STANDARDS ANALYTICAL STANDARDS AND CERTIFIED REFERENCE MATERIALS FOR CONSTITUENTS OF MEDICINAL PLANTS

sh9885_Update Phytopharma Standards Brochure_v1.indd 1 07/07/16 2:27 pm PHYTOCHEMICAL STANDARDS Analytical Standards and certified reference materials for constituents of medicinal plants

Long before the advent of modern medicine and synthetically produced pharmaceuticals, herbal medicines have been used for the treatment and prevention of diseases and afflictions. Based on the empirical knowledge of generations, rich traditions of natural medicine have evolved independently in different regions of the globe. Nowadays, herbal medicinal products continue to play an important role in global health care. Traditional Indian medicine (Ayurveda) and traditional Chinese medicine (TCM) are increasingly popular in the Western world. Due to the complexity of plant derived materials, and the fact that herbal medicinal products have supposedly been safely used for ages, until a few years ago, no significant quality control had been demanded for these products by the authorities (quite the opposite of synthetically produced pharmaceuticals). However, in the last two decades, the perception has changed, and it is agreed that herbal medicinal products do in fact need effective quality control in order to ensure that the products are safe and meet established quality standards. The composition of a plant may vary dramatically depending on season or location of harvest. Therefore, active or potentially harmful toxic components may vary in concentration and need to be controlled. Sigma-Aldrich offers a substantial portfolio of analytical standards and reference materials for key ingredients of the most widely used medicinal herbs. The portfolio comprises more than 600 products and continues to grow. If you don’t find the product that you require in this brochure, please browse the up-to-date portfolio on sigma-aldrich.com/medicinalplants or contact us. While all analytical standards are tested thoroughly for identity and chromatographic purity, we also offer an expanding portfolio of primary pharmaceutical standards for herbal medicinal product analysis as well as an increasing number of TraceCERT® Certified Reference Materials (CRM). This brochure is focusing on the natural plant constituents. However, as shown on page 40, Sigma-Aldrich offers also other standards and reference materials that are required for the testing of herbal medicines such as , mycotoxins, inorganic standards and microbiological CRMs.

Contents

Product Listings Primary Pharmaceutical Standards...... 3 Index by Plant Genus...... 14–33 Plant Extracts...... 4 Alphabetical Index ...... 34–39 Organic Certified Reference Materials TraceCERT®...... 5

Other Reference Materials Selected Analytical Applications Pharmacopoeia Compendial Standards...... 40 Separation of Silymarin Components...... 6 Inorganic Certified Reference Materials ...... 40 Separation of the Components of Withania somnifera (Ashwagandha) ...... 8 Standards...... 40 Separation of the Components of Boswellia ...... 10 Mycotoxin Standards...... 40 Separation of Ginsenosides ...... 12 Microbiological CRMs (Vitroids)...... 40

2 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 2 07/07/16 2:28 pm Primary Pharmaceutical Standards

Description Package Cat. No. trans-Anethol 100 mg 00130595 p-Anisaldehyde 50 mg 05320590 10 mg 01760595 Apigenin-6,8-diglucoside (Vicenin 2) 10 mg 03980585 Apigenin 7-glucoside 10 mg 00720585 Apigenin 7-O-glucuronide 10 mg 04490590 Arbutin 50 mg 00890590 β-Asarone 25 mg 02890590 Asiaticoside 10 mg 04560590 Aspalathin 10 mg 03520585 25 mg 00090590 Bilobalide 10 mg 00760595 (−)-α-Bisabolol 100 mg 00320188 Bisabolol oxide A 25 mg 00630590 (−)-Bornyl 50 mg 00400585 Camphene 100 mg 01410590 (dl) 100 mg 02070595 (+)-3-δ-Carene 100 mg 00410590 Carnosic acid 10 mg 05330590 50 mg 04270590 (−)-Carvone 100 mg 00290595 10 mg 01940590 (+)- 10 mg 03910590 Our selection of analytical standards for active substances 25 mg 00500590 and marker compounds of herbal medicinal products includes a growing range of primary pharmaceutical standards. These standards 1,8-Cineole () 100 mg 00020590 are manufactured and qualified by HWI-Analytik in Rülzheim p-Coumaric acid 50 mg 03200595 (Germany) and exclusively distributed by Sigma-Aldrich. Coumarin 50 mg 01260595 10 mg 00280590 The absolute content determination of these products is performed 50 mg 05340590 by quantitative NMR (qNMR). qNMR is increasingly applied not 10 mg 05370590 only for content assignment of natural products, but also by the 10 mg 01710580 pharmaceutical industry in general as an orthogonal method and alternative to the very common but laborious “mass balance” Ellagic acid 50 mg 05350590 approach. The Sigma-Aldrich in-house produced organic TraceCERT® Epicatechin 10 mg 03940590 certified reference materials also use qNMR for quantification (−)-Epicatechin 3-gallate 10 mg 03950590 (see page 5). Epigallocatechin 10 mg 03960590 10 mg 03970590 In addition to the quantitative value determined by qNMR, the Eriocitrin 10 mg 02660590 certificates of the primary pharmaceutical standards from HWI also Eucalyptol (1,8-Cineole) 100 mg 00020590 list a value for the chromatographic purity. These two values may differ since not all impurities are detected by chromatography. 100 mg 01050595 For quantitative calculations, the qNMR value should be used. (+)-Fenchone 100 mg 00380590 50 mg 05360590 25 mg 05380590 More detailed information about these products can be found Geranyl acetate 100 mg 01290190 in articles published in our Analytix magazine (issue 1/2010 Ginkgolic acid C15:1 10 mg 02580185 pages 11 – 15) to be downloaded at Ginkgolic acid C17:1 10 mg 01390590 sigma-aldrich.com/analytix Ginkgolid A 25 mg 00770590 Ginkgolide C 25 mg 01490590 The portfolio of primary pharmaceutical standards currently Ginsenoside Rb1 10 mg 00170580 consists of over 100 products listed below. This selection is Ginsenoside Re 10 mg 03000590 continuously growing, and an up-to-date listing can be found at: Ginsenoside Rg1 10 mg 00370580 sigma-aldrich.com/phytopharma Glycyrrhizic acid ammonium salt 50 mg 01250570 Harpagoside 25 mg 00420580 Hederacoside C 10 mg 00930585

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sh9885_Update Phytopharma Standards Brochure_v1.indd 3 07/07/16 2:28 pm Description Package Cat. No. Description Package Cat. No. α-Hederin 10 mg 01240585 10 mg 03920590 Herniarin 10 mg 02250595 10 mg 05400590 Hesperidin 25 mg 04650590 10 mg 03810585 Hulupinic acid 10 mg 01090595 Osthole 10 mg 02150595 Hypericin 10 mg 00190585 (−)-β-Pinene 100 mg 00080590 Hyperoside 25 mg 00180585 α-Pinene 100 mg 00040590 (1S,2R,5R)-(+)-Isomenthol 25 mg 04280590 50 mg 03930590 10 mg 03820585 (+)- 100 mg 04620590 (−)-Isopulegol 50 mg 04570595 dihydrate 50 mg 00200595 Isoquercitrin 25 mg 00140585 Quercetin 3-glucuronide 25 mg 00310590 Isorhamnetin 10 mg 04290585 25 mg 00740580 Isorhamnetin-3-O-β-D glucopyranosyl-(1š2)-β- 10 mg 00960590 25 mg 00390580 D glucopyranosyl-(1š6)-β-D glucopyranoside Rutin trihydrate 50 mg 00300590 10 mg 01120590 Sabinen hydrate 50 mg 04630590 10 mg 00550580 Salidroside 10 mg 05410590 Kämpferol-3-glucosid 10 mg 04500585 Sennoside A 25 mg 01870575 Larixylacetat 50 mg 02730595 Sennoside B 25 mg 00530580 (R)-(+)- 100 mg 00590590 β-Sitosterol 10 mg 05410590 100 mg 00350190 Silybin 25 mg 02000585 25 mg 03880590 Stevioside 25 mg 05420590 Luteolin 7-glucoside 10 mg 03600585 Taxifolin 10 mg 03890585 Luteolin-7-O-β-D-glucuronide 10 mg 04480585 Terpinen 4-ol 50 mg 03900590 Menthofuran 50 mg 04580595 γ-Terpinene 100 mg 04640590 (+)-Menthofuran 50 mg 04580595 α-Terpineol 100 mg 03420590 (−)- 100 mg 00580590 100 mg 00670590 (-)-Menthone 100 mg 04660585 10 mg 03240595 Menthylacetat 100 mg 04590595 10 mg 02010595 Myrcene 50 mg 04600585 10 mg 00820580 10 mg 05390590 10 mg 00840595 Myricitrin 10 mg 02180585 Vitexin 2-O-rhamnoside 10 mg 00660585 trans-Nerolidol 50 mg 04610590 Xanthohumol 10 mg 01130595

Plant Extracts

As a brand new addition to the HWI portfolio we are introducing extracts of some of the most widely used medicinal plants. The extracts are qualified as secondary standards, providing quantitative values for one or several marker ingredients. The values are traceable to HWI primary pharmaceutical standards.

Description Marker Ingredients Package Size Product Number Camellia sinensis extract Epigallocatechin gallate 150 mg 05495001 Crataegus spp extract Vitexin rhamnoside 150 mg 05095001 Ginkgo biloba extract Blobalide, Ginkgolide A 150 mg 05485001 Harpagophytum procumbens extract Harpagoside 150 mg 05125001 extract Hypericin 150 mg 05295001 Panax ginseng extract Ginsenosides Rb1+Rg1 150 mg 05115001 incarnata extract Isovitexin 150 mg 05085001 Senna extract Sennoside B 150 mg 05475001 Silybum marianum extract Silybin A+B 150 mg 05135001 Valeriana officinalis extract Valerenic acid 150 mg 05105001

4 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 4 07/07/16 2:28 pm Certified Reference Materials (CRM) TraceCERT®

For ISO/IEC 17025 accredited labs, it is important to show traceability of all results to an internationally recognized standard, so for calibration, certified reference materials (CRMs) must be used. Our rapidly expanding TraceCERT® product range includes an increasing number of certified reference materials for natural products. TraceCERT products are manufactured under ISO/IEC 17025 and ISO Guide 34 double accreditation, which is the highest achievable quality level for reference material producers and which is also referred to as “the gold standard”. All TraceCERT products are delivered with a comprehensive certificate according to ISO Guide 35 including properly calculated uncertainties taking into account homogeneity and stability of the material. These neat CRMs are certified by quantitative NMR (qNMR) and traceable to NIST SRM.

The complete range of organic TraceCERT products can be found at: sigma-aldrich.com/organiccrm So far the following natural products CRMs are available:

Description Package Cat. No. Description Package Cat. No. p-Anisaldehyde 100 mg 43621 Glutaric acid 100 mg 89147 L-Ascorbic acid 100 mg 57803 Glycolic acid 100 mg 94815 Benzyl 100 mg 39971 Linalool 50 mg 61706 Benzyl benzoate 1mL 55177 Magnesium L-lactate hydrate 100 mg 40394 Betaine 50 mg 30056 L-(−)-Malic acid 100 mg 09172 Biotin 50 mg 91827 Malonic acid 100 mg 68714 trans- 50 mg 51868 Quinine 50 mg 69311 100 mg 56396 50 mg 06859 (+)-Carvone 100 mg 79245 Resorcinol 100 mg 53363 Citric acid 100 mg 94676 trans- 100 mg 76511 Coumarin 100 mg 72609 Safrole 100 mg 08010 p-Cymene 100 mg 49679 50 mg 52341 Digoxin 50 mg 04599 Sodium propionate 100 mg 49894 Eucalyptol 100 mg 95656 Succinic acid 100 mg 49893 Eugenol 100 mg 79891 L-(+)- 100 mg 41447 trans- 50 mg 52229 Vanillic acid 50 mg 68654 Fumaric acid 100 mg 76635 50 mg 30304 100 mg 91215

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sh9885_Update Phytopharma Standards Brochure_v1.indd 5 07/07/16 2:28 pm HPLC Methods for Separation of Medicinal Plant

To demonstrate the excellent separation capability and versatility of Supelco brand Ascentis Express columns and sample preparation 1. MILK THISTLE (SILYBUM MARIANUM) products, examples of analytical applications for the separation of key ingredients of widely used herbal medicinal products are shown on Introduction the following pages. Silymarin, derived from the milk thistle plant (Silybum sp.), has been Since the characteristic components of a plant are often structurally used as a natural remedy for the treatment of a number of liver very similar, their separation can be challenging and requires both diseases as well as in the protection of the liver from potential toxins. good skills and the best suited separation columns. The applications More recently, silymarin has been connected to antitumor promoting have usually been developed and optimized using a mixture of the activity [1]. It is therefore of interest to have available analytical available analytical standards, and are then applied to either plant methods for the analysis of silymarin components in various matrices. extracts or commercially available herbal medicinal products. The The silymarin complex consists of several closely related, biologically four examples include various chemical compound classes such as active components. The objective of this study was to investigate (Silybum), Steroidal lactones (Withania), Triterpenoids several modern stationary-phase chemistries for optimal selectivity (Boswellia and Ginseng). towards the development of an efficient method for the analysis of silymarin. The method would optimally provide baseline resolution Figure 1. Structures of known biologically active silymarin components for nine of the known components of silymarin in less than 15 minutes. Silybin A Initial screening experiments were used to select a single combination of stationary phase and organic modifier that demonstrates the greatest potential for the separation. The information from subsequent optimization experiments was processed with simulation software to predict an optimized set of conditions. Finally, the predicted conditions were confirmed using the analysis of an herbal supplement obtained from a local drug store.

Silybin B Experimental The screening protocol utilized five Ascentis® Express stationary phases including C18, C8, RP-Amide, Phenyl-Hexyl and Taxifolin Isosilybin A pentafluorophenylpropyl (F5). Gradient elution with two distinct organic modifiers was performed. Injections of a standard containing nine of the known constituents of silymarin (Figure 1) were made under each condition. The HPLC screening method employed gradient elution from 5%–95% of either or acetonitrile. The aqueous component of the mobile phase was 0.1% formic acid (pH 2.6). Isosilybin B In order to optimize the separation, separate chromatographic Silydianin analyzes at two different gradient slopes and two temperatures were performed. These four runs were then processed using ACD LC-Simulator software (Toronto, ON, Canada) and a predictive model was used to develop conditions that would provide baseline resolution of all peaks in less than 15 minutes. The conditions were then confirmed, using both standards and a commercially available milk thistle herbal supplement. Quercitrin Results and Discussion Using a simple peak counting approach, the combination of the C18 stationary phase along with methanol as the organic modifier resulted in the highest number (nine) of visible peaks. Apigenin-7-D- A representative chromatogram is shown in Figure 2. Other combinations of stationary phase and organic modifier produced between six and eight peak responses.

6 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 6 07/07/16 2:28 pm Four separate chromatographic runs using the C18 stationary phase Finally, an herbal supplement labeled as containing milk thistle along and methanol modifier were conducted, where the gradient slopes with dandelion, and licorice was extracted using water: were varied (5% and 10% ramp) at two different temperatures 50:50, v/v and analyzed. As shown in Figure 4, all 9 of the targeted (30 °C and 60 °C). The data was then analyzed using ACD LC-Simulator components could be observed in the herbal supplement material. to predict the most suitable optimized conditions. Comparison to the experimental data shown in Figure 3 confirms good agreement Figure 4. Identification of silymarin components from a commercial between the predicted (not shown) and actual chromatography. Because the suggested conditions ran to just 45% organic, an natural supplement additional step to 100% organic was included to elute potential See Figure 3 for conditions and peak IDs. Sample extracted with 50:50 hydrophobic components from a natural sample. water:ethanol. Gradient extended to 100% methanol to elute potential hydrophobic sample components.

Figure 2. Initial separation of silymarin components using C18 2 stationary phase and methanol as the organic modifier

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0 10 10 Min

02468 10 12 Min Conclusions Figure 3. Experimental confirmation of predicted optimized conditions Stationary phase screening at the onset of method development, column: Ascentis® Express C18, 10 cm × 3.0 mm I.D., 2.7 µm especially when dealing with a complex set of analytes, provides particle size an easy means of analytical method development. As shown in the mobile phase A: water with 0.1% formic acid study, a few short experiments, coupled with powerful prediction software, provided chromatographic conditions suitable for the mobile phase B: methanol analysis of biologically active milk thistle components. The conditions gradient: min %A %B that were developed should prove useful in natural supplement, 0 65 35 raw material and/or biological monitoring of silymarin complex 3 65 35 components. The analytical standards for the analytes described in 13 55 45 this article are listed in the table below. 15 55 45 flow rate: 0.6 mL/min temp.: 35 °C 1. Taxifolin Description Pack Size Cat. No. det.: UV, 254 nm 2. Silychristin Apigenin-7-glucoside 10 mg 00720585 injection: 20 µL 3. Apigenin-7-D-glucose 4. Silydianin Isosilybin A 5 mg 97326 sample: 9 milk thistle related 20 µg/µL in 86:14, 5. Quercitrin Isosilybin B 5 mg 95684 water:methanol 6. Silybin A Quercitrin 25 mg 00740580 7. Silybin B Silybin A, primary reference standard 10 mg 02000585 3 8. Isosilybin A Silybin B 5 mg 59527 5 9. Isosilybin B Silychristin 10 mg 51681 Silydianin 10 mg 30494 Taxifolin 25 mg 78666 1 2 Reference standards for active components of silymarin. 6 7 4 8 9

0246 8 10 12 14 Reference Min 1. Lee, J. I.; Hsu, B. H.; Wu, D.; Barrett, J. S. Journal of Chromatography A 2006, 1116, 57–68.

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sh9885_Update Phytopharma Standards Brochure_v1.indd 7 07/07/16 2:28 pm 2. ASHWAGANDHA (WITHANIA SOMINFERA) Figure 1. Structures of Selected Withania Constituents The dried roots of Withania somnifera are the source for 12-Deoxywithastramonolide Withaferin A Ashwagandha, one of the most popular remedies in traditional­ Indian medicine (Ayurveda). Ayurvedic medicine is becoming increasingly popular in the western world, too, as reflected by the existence of a United States Pharmacopeia (USP) monograph for powdered Ashwagandha roots2 and a British Pharmacopeia (BP) monograph for W. sominerfa root for use in Traditional Herbal Medicinal Products (THMP).3 Withanolide A Withanolide B Withanone The traditionally benign health effects are very diverse and include aphrodisiac, rejuvenative and life-prolonging properties.4 Beneficial effects are also supported by recent bioactivity studies: Withaferin A has been shown to have significant anticancer activity in animals.5 The characteristic constituents belong to a group of steroidal lactones consisting of a steroidal scaffold attached to a six-membered lactone ring. The structures are shown in Figure 1. Withanoside IV Withanoside V Fresh Plant

HPLC Analysis of Withania Constituents Using Ascentis® Express Columns As part of a large number of natural health product studies recently conducted, many of the main constituents of Withania were screened on several modern Fused-Core® stationary phases. The results from the screening effort showed that the Ascentis Express F5 and the Ascentis® Express Phenyl-Hexyl phases provided improved selectivity over the C18 stationary phase. Both phases, presumably due to their intrinsic rigidity, are known to provide enhanced shape selectivity. The shape selectivity component is often found to be useful for the separation of closely related compounds with rigid structures. Dried Root Figure 2 shows a comparison of Withania standard constituents separated using the USP method to an optimized separation with Ascentis Express Phenyl-Hexyl. The USP method calls for a long, 40-minute gradient and the use of a 25 cm × 4.6 mm C18 column. Even with this lengthy system, only marginal separation of Withanolide A and Withanone is obtained. Conversely, a 15-minute gradient utilizing a shorter 10 cm × 2.1 mm phenyl-hexyl phase provides baseline separation of all components. Figure 3 shows the separation of Ashwagandha extract constituents using both systems. The use of the phenyl hexyl column is again shown to provide improved resolution in a shorter period of time and with approximately 3x greater sensitivity. Note that only those components that could be confidently identified are noted. Similar results were obtained utilizing the Ascentis Express F5 stationary phase (data not shown). Conclusion A fast method with full resolution of 7 constituents from the Ashwagandha root was achieved on an Ascentis Express Phenyl-Hexyl Fused-Core particle column.

8 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 8 07/07/16 2:29 pm Figure 2. Comparison of Withania Standard Separation Using a Discovery C18 Conditions for Figures 2 and 3 Standard C18 vs Optimized Ascentis Express Phenyl-Hexyl Method column: Discovery C18, 25 cm × 4.6 mm I.D., 5 µm (504971) 4 5 Discovery® C18 3 6 mobile phase A: phosphate buffer* compound 7 elutes 4 5 mobile phase B: acetonitrile atDiscov 24 minutesery® C18 3 6 compound 7 elutes gradient: Min. %A %B at 24 minutes 7 1 0.0 95.0 5.0 2 7 18.0 55.0 45.0 Discovery® C18 1 4 5 3 2 6 25.0 20.0 80.0 compound 7 elutes 4 5 28.0 20.0 80.0 Discovat 24 minutesery® C18 3 6 compound 7 elutes 30.0 95.0 5.0 7 at 24 minutes 1 40.0 95.0 5.0 12 14 16 18 2 20 22 24 7 flow rate: 1.5 mL/min. 1 12 14 16 18Min 2 20 22 24 temp.: 27 °C Min det.: 227 nm injection: 20 µL samples: S tandard: 20 µg/mL each in 80:20 14 16 18 20 22 24 12 water: methanol Ascentis® Express Phenyl-Hexyl Min 4 12 14 16 18 205 22 24 Extract: As per USP (1) compound 7 elutes Ascentis® Express Phenyl-Hexyl 3 4 6 * Dissolve 0.14 g of potassium dihydrogen phosphate in 900 mL water, at <9 minutes Min 5 compound 7 elutes add 0.5 mL of phosphoric acid, dilute with water to 1000 mL, and mix. 3 6 at <9 minutes

Ascentis® Express Phenyl-Hexyl 4 7 1 2 5 Discovery C18 Conditions for Figures 2 and 3 compound 7 elutes 6 Ascentis® Express Phenyl-Hexyl 3 4 7 at <9 minutes 1 2 5 column: Ascentis Express Phenyl-Hexyl, 10 cm × 2.1 mm I.D., compound 7 elutes 3 6 2.7 µm (53336-U) at <9 minutes mobile phase A: water 0 24687 10 mobile phase B: acetonitrile 1 2 Min gradient: Min. %A %B 0 246810 1 7 0.0 80.0 20.0 Min 2 10.0 0.0 100.0 FigureDiscovery® 3. Comparison C18 of Ashwagandha Extract3 Component 10.5 0.0 100.0 compound0 7 elutes246810 11.0 20.0 80.0 SeparationDiscovery® C18 Using a Standard C18 vs Optimized3 Ascentis Express at 24 minutes Min 15.0 20.0 80.0 0compound 7 elutes241 6810 Phenyl-Hexylat 24 minutes 4 flow rate: 0.3 mL/min. Min 2 5 1 temp.: 35 °C 2 4 Discovery® C18 3 5 7 det.: 227 nm compound 7 elutes injection: 5 µL Discovat 24 minutesery® C18 3 7 compound 7 elutes 1 samples: same as Discovery C18 4 at 24 minutes 2 5 10 1 20 4 2 5 7 Description Pack Size Cat. No. 10 Min 20 12-Deoxywithastramonolide 10 mg 94187 Ascentis® Express Phenyl-Hexyl Min 3 7 compound 7 elutes Withaferin A 10 mg 89910 Ascentis® Express Phenyl-Hexyl 3 at <9 minutes Withanolide A 10 mg 74776 compound 7 elutes 10 20 at <9 minutes 4 Withanolide B 10 mg 94284 Min1 5 10 20 Withanone 10 mg 90896 2 4 Ascentis® Express Phenyl-Hexyl 1 3 5 Min Withanoside IV 10 mg 94186 compound 7 elutes 7 2 Withanoside V 10 mg 66042 Ascentis®at <9 minutes Express Phenyl-Hexyl 3 7 compound 7 elutes Ascentis Express Phenyl-Hexyl Column 10 — 53336-U 4 at <9 minutes 1 5 cm x 2.1 mm I.D., 2.7 µm 0246810 2 4 Standards and Columns used for this application. 1 5 024Min 687 10 2 Min References 7 1. USP 34, Dietary Supplements, Ashwagandha 1079. 0246810 2. BP 2011, Withania somnifera roots for THMP, 3674. 3. Agarwal, A.; Murali, B.; “Quality Assessment of Selected Indian Medicinal Plants”; Min 0246810 Volume 1. Min 4. Singh, G.; Sharma, P.K.; Dudhe, R.; Singh, S.; Annals of Biological Research, 1 (3); 56–63.

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sh9885_Update Phytopharma Standards Brochure_v1.indd 9 07/07/16 2:29 pm 3. FRANKINCENSE (BOSWELLIA SACRA) The trees of the genus boswellia have been used in traditional medicine for thousands of years as an anti-inflammatory agent. Its resin is known as frankincense or olibanum and is still widely used in dietary supplements and in herbal medicinal products. The most characteristic components are a group of pentacyclic triterpene acids of which β-boswellic acids are the major biologically active constituents. Sigma-Aldrich® offers six boswellic acids as analytical standards and two neat standards of α+β mixtures for use in research and quality control. Separation of Boswellic Acids Several conditions, using a variety of solid phases, have been screened for their suitability to separate six boswellic acids. The shortest analysis time was achieved using an Ascentis Express Column (2.7 μm particle size, L × I.D. 10 cm × 3.0 mm) and acetonitrile/phosphoric acid as eluents. Figure 2 shows the chromatograms of the ethanolic extract of a boswellia herbal supplement as well as of a mixture of the six analytical standards.

Figure 1. Chemical Structures of the Boswellic Acids

CH3 H3C CH3 CH3 H3C H3C

CH3 CH3 CH3 H C H3C CH3 H 3 CH3 H H3C CH3 H O H CH3 H CH3 H CH3 HO HO H3C O H3C H H3C H H3C H O OH O OH O OH

80342 06813 49873 β-boswellic acid α-boswellic acid 3-O-Acetyl-β-boswellic acid

H3C CH3 CH3 CH3 H3C H3C CH CH CH 3 O 3 O 3 H C 3 CH3 H H3C CH3 H H3C CH3 H O O H CH3 H CH3 H CH3 H3C O H3C O HO H3C H H3C H H3C H O OH O OH O OH

56208 74607 78535 3-O-Acetyl-α-boswellic acid 3-O-Acetyl-11-keto-β-boswellic acid 11-keto-β-boswellic acid

10 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 10 07/07/16 2:29 pm Figure 2. Experimental Conditions and Chromatograms of the Description Pack Size Cat. No. Separation of Boswellic Acids 3-O-Acetyl-11-keto-β-boswellic acid 5 mg 74607 3-O-Acetyl-α-boswellic acid 5 mg 56208 Column: Ascentis Express Phenyl-Hexyl, 10 cm × 3.0 mm 3-O-Acetyl-β-boswellic acid 5 mg 49873 I.D., 2.7 µm (53345-U) 3-O-Acetylboswellic acid, mixture of α 5 mg 96729 Mobile Phase: (A) 0.1% phosphoric acid; (B) acetonitrile and β Gradient: 50% B for 0.5 min; to 100% B in 4.5 min; α-Boswellic acid 10 mg 06813 held at 100% B for 5 min β-Boswellic acid 5 mg 80342 Flow Rate: 0.6 mL/min Boswellic acid, mixture of α and β 5 mg 63850 Pressure: 2390 psi (165 bar) 11-Keto-β-boswellic acid 5 mg 78535 Column temp.: 35 °C Ascentis Express Phenyl-Hexyl, 2.7 10 cm × 3.0 mm 53345-U Detector: UV at 210 nm Micron HPLC Column Injection: 5 µL Analytical Standards of Boswellic Acids and Column Used. Sample(s): 6 Boswellic acids 50 µg/mL in 70:30, water:methanol extract in 50:50, water:ethanol Extraction: 1. Weigh 100 mg Bosewellia Herbal Supplement 2. Add 10 mL ethanol 3. Sonicate for 30 min at 40 °C 4. Dilute: 100 µL extract in ethanol, 400 µL ethanol, 500 µL water

1. 11-Keto-β-boswellic-acid 2. 3-O-Acetyl-11-keto-β-boswellic-acid 3. α-boswellic-acid 4. β-boswellic-acid 5. 3-O-Acetyl-α-boswellic-acid 6. 3-O-Acetyl-β-boswellic-acid A. Boswellia Extract

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B. Analytical Standards at 3 5 50 µg/mL of Each Component 4 6 1 2

0246810 Min

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sh9885_Update Phytopharma Standards Brochure_v1.indd 11 07/07/16 2:29 pm 4. AMERICAN GINSENG (PANAX QUINQUEFOLIUS) Belonging to the plant genus panax, ginseng is one of the most well-known herbal medicines. It has been used in traditional Chinese medicine for centuries, but has also become very popular in the Western world. Medicines derived from the ginseng root are used in the treatment or prevention of many health problems including anxiety, asthma, diabetes, headache, stress, depression and erectile dysfunction, among many others. The unique compounds of panax are triterpenoid , called ginsenosides. Their potential effects in humans are being studied intensively.

Figure 1 Chemical structures of the analyzed ginsenosides

OH OH OH OH OH OH OH OH OH OH O OH OH OH O O OH OH OH OH OH OHO O O O OH OH OH OO O O O OH OHO OH CHOH O O OO O OH OH 3 O O CH O O OH OH OH CH OH CH 3CH OO 3 OH OH 3 OH 3 CH CH CH CH OO OO OH OH OH CH3 3 3 OH3 CH 3 O CH CH CH OHOH H CH3 CH3 OH H 3 O 3 OH 3 3 OH OH OH H OH OH OH OH O O OH OHOH OH CH H H OH H CH3 OH OH 3 OH CH H H OH OH OH CHOH3 OH OH 3 CH CH CH3 CH3 H CH3 CH3 CH CH H 3 3 CH CH 3 3 3 3 H CH CHCH CH OH CH3 CH3 H CH CH 3 33 H 3 H OH CH3 CH33 H 3 H OH O OH OH OH H CH3 O CH3 HOH CHOH H OCH O 3 H HCH CH3 H 3 CH CH O 3 OH O H H 3 3 OO H OHO O O OH O H OH O 3CH CHH O O CH OH H O OH CH 3 OH OH H H OO 3 CH3 H H 3 CH3 3CH CH3CH CH OH OO 3CH CH CH CH OH OH 3 3 3 OO OO 3 CH3 3 CH3 OH OH OH OH OH OH OHOH OH O OH OH OO Ginsenoside RB Ginsenoside RB O O 1 OH OH OH OH OH OH 2 OHO O O OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH O OHO O O OH OH OH OH OH OH O OH OH OH O O O OH OH OH O OH OH OH OH OH OHCH3 CH OH OH OH OO OH OH OH O O OH OH 3 OH OHO OHCH O O OH 3 OH OH OH CH3 CH3 CH3 CH3 CH OH CH CH CH OO OH OH3 OH OH OH H OH3 OH 3 3 CH OO OO OH OH OH 3OO CH3OO CH OH H H H OH3CH CH3CH 3CH CH CH 3 CH3 3CH CH 3 3 3 OH OH CHOH CH CH OH H OH3 OH CH CH 3 3 3 OH OH H 3 3 H OH H H CH3H CH3 CH CH H CH3 CHCH33 CHH 3 H OH OH OH CH CH CH3 3 3 CH3 3 3 CH 3CH H OH OH 3 CH CHCH CH H OH HOH OH CH3 OH CHCH3 CH3 H H CH3 3 3 3 H H CH3 H HCH3 CH3 OH O OH 3 OH 3 O O 3CH CH3 O O H O O OH OO O O CH3 H OHO H O O H H CHCH H CH3 CH3 3CH CHH OH H H 3 3 OH CH 3 OH CH CHCH CH OH OH O 3 CH3 3 3 3 3 OH OH OH O OH OHOH H OH OOH O OH O OH OH OO 3CH H CHH H H OH OHOH OH CH OO3 OOCH 3CH OH OH OO 3CH 3 CHCH3 O O 3 CH3 CH3 OH OH O 3 O OO O O OH O O O OH OH OH OH OH Ginsenoside Rc OH OH OH OH O OH OHOH Ginsenoside RD OH OH OH OH OH OH OH OH OH OH OH OH OH OH O OH OH OH

OH CH3 OH OH OH OH CH3 CH OH OH OH CH CH 3 OH OH OH OH 3 3 OH OH OH CH 3CH 3 OH OO CHCH3 CH OO 3 OO 3CH CHCH3 H C OH O3 3 3 CH3 OH OHH CH OH HH CH3 3 H CHCH3 CH 3 OHOH 3 CHCH3 CHCH3 HH CH CH CH CH H 3 3 O O O O3CH 3 CH3 3 3 3 OH OH H CH H CH33 H CH3 OH O OH OH OHOH OH O OH OH HH H CH CH OH OH 33CH CH33OO OO OH OH 3CH CH O OH O O 3

O OO OHOH OHOH OH OH OH OHOH OHOH OH OH OO OH

OH OH CHCH33 Ginsenoside Re Ginsenoside Rf Ginsenoside Rg1 OHOH OHOH OH OH OHOH

OH OH OOOO HHC 3 3C CHCH3 3 12 OHOH Phytochemical Standards HH CHCH3 3 CH CH H CH3 3 CH3 3 H

H CH H CH3 3 sh9885_Update Phytopharma Standards Brochure_v1.indd 12 07/07/16 2:29 pm OH OH OHOH HH 3CH CH CH O OH 3 CH3 3 O OH

OO OHOH

OHOH Gensenoside Re Ginsenoside Rb1 Ginsenoside Rd

Separation of Ginsenosides in American Ginseng Figure 3 Chromatogram of theGinsenoside Rc American ginseng root extract We achieved a very good separation of seven different ginsenosides Extraction method used for ginseng root: Ginsenoside Rg1 using an Ascentis Express C18 column. The application was first NSF International Ground Plant Material:Ginsenoside Rb2 320 mg optimized using a ginsenoside standard mixture (Figure 2) and was (or 36 mg for XRM material) then applied to a sample of American ginseng root (Figure 3). 0246 Extraction Solvent: 8110 mL 50:50,01 water:ethanol21 4 The seven targeted analytes are ginsenosides RB1, RB2, Re, Rc, RD, Rf STimeonication: (min) 30 min and Rg (structures shown in Figure 1). The experimental conditions 1 Temp.: 50 °C and chromatograms are shown below.

Figure 2. Chromatogram of the standard mixture (50 µg/mL each component in 82:18, water:methanol) Ginsenoside Rb1 Experimental Conditions Ginsenoside Rc Gensenoside Re

Column: Ascentis Express C18 15 cm × 4.6 mm, Ginsenoside Rg1 2.7 µm particle size Mobile Phase: (A) water

Mobile Phase: (B) acetonitrile Ginsenoside Rb2 Gradient: min %A %B 0 75 25 02468101214 1.5 75 25 Time (min) 13.5 15 85 14.5 15 85 Flow Rate: 1.5 mL/min Description Pack Size Cat. No. Temp.: 60 °C Ginsenoside Rb1 primary pharmaceutical 10 mg 00170580 Detector: 205 nm reference standard

Injection: 10 µL Ginsenoside Rb2 analytical standard 10 mg 41868 Ginsenoside Rc analytical standard 10 mg 44987 Ginsenoside Rd analytical standard 10 mg 01518 Ginsenoside Re primary pharmaceutical 10 mg 03000590 reference standard Gensenoside Re Ginsenoside Rb1

Ginsenoside Rd Ginsenoside Rf primary pharmaceutical 10 mg 01580590 reference standard Ginsenoside Rc Ginsenoside Rg1 primary pharmaceutical 10 mg 00370580 reference standard Ginsenoside Rg1

Ginsenoside Rb2 Ginseng root from Panax quinquefolium 5 mg G7253 (American ginseng) 02468101214 Ascentis Express C18 15 cm x 4.6 mm, 2.7 µm 1 EA 53829-U particle size Time (min) Products Used. Ginsenoside Rb1 Ginsenoside Rc Gensenoside Re Ginsenoside Rg1 Ginsenoside Rb2

02468101214 Time (min)

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sh9885_Update Phytopharma Standards Brochure_v1.indd 13 07/07/16 2:29 pm Product List by Plant Genus

On the following pages, a list of almost 100 of the most widely used medicinal plant genera are listed, showing the most relevant constituents that can be used as analytical markers for each corresponding plant.

Compound Cat. No. Compound Cat. No. Acacia sp. Luteolin 72511 Apigenin 7-glucoside* 00720585 Luteolin 7-glucoside* 03600585 Apigenin 7-glucoside 44692 Luteolin 7-glucoside 49968 Catechin 5-O-gallate 89106 Rutin trihydrate* 00300590 (+)-Catechin* 03910590 Scopoletin 38332 (+)-Catechin 43412 Aesculus sp. 3,3'-Di-O-methylellagic acid 4'-xylopyranoside 90905 Allantoin 93791 Epicatechin* 03940590 Esculin hydrate 06212 (−)-Epicatechin 68097 Fraxin 80533 Epicatechin 3-gallate (-)* 03950590 Kaempferol* 00550580 Epigallocatechin gallate* 03970590 Kaempferol 96353 (−)-Epigallocatechin gallate 93894 Quercetin dihydrate* 00200595 Gallic acid** 91215 Allium sp. (−)-Gallocatechin 01388 (+)-L-Alliin 72805 48798 trans-Ferulic acid** 52229 Hordenine 61207 Kaempferol* 00550580 Hyperoside* 00180585 Kaempferol 96353 Isovitexin* 01120590 Kaempferol 3-glucoside 68437 Isovitexin 67135 Protocatechuic acid* 03930590 Luteolin 7-glucoside* 03600585 Protocatechuic acid 08992 Luteolin 7-glucoside 49968 Quercetin 3-glucoside 16654 (±)- 52186 Quercetin dihydrate* 00200595 Oleanolic acid* 03920590 Resorcinol** 53363 Oleanolic acid 42515 Spiraeoside 91802 p-Hydroxybenzoic acid PHR1048 Aloe sp. Quercetin 3-glucoside 16654 Aloe-emodin 93938 Quercetin dihydrate* 00200595 Aloenin A 41757 Quercitrin* 00740580 Aloin A 50292 Rutin trihydrate* 00300590 Chrysophanol 01542 Salicylic acid** 52341 Salicylic acid** 52341 Spiraeoside 91802 Ammi sp. (+)-α-Terpineol 83073 Khellin 00899 Vitexin* 00840595 Anacardium sp. Vitexin 49513 (15:0)-Anacardic acid 05506 Achillea sp. Cardanol 04016 Apigenin* 01760595 5-Pentadecylresorcinol 91822 Apigenin 42251 Protocatechuic acid* 03930590 Apigenin 7-glucoside* 00720585 Protocatechuic acid 08992 Apigenin 7-glucoside 44692 Andrographis sp. (−)-Bornyl acetate 45855 Andrograpanin 19443 Casticin 16382 Andrographolide 90281 Chamazulen 91595 14-Deoxy-11,12-didehydroandrographolide 55549 1,5-Dicaffeoylquinic acid 16917 7-O-Methylwogonin 41442 (−)-β-Elemene 63965 Neoandrographolide 49879 Eucalyptol (1,8-Cineole)** 95656 Angelica sp. Eucalyptol (1,8-Cineole)* 00020590 Angelicin 18118 Eucalyptol (1,8-Cineole) 29210 Bergapten 69664 Luteolin* 03880590 (−)-α-Bisabolol* 00320188

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

14 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 14 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. (−)-α-Bisabolol 95426 Isoquercitrin* 00140585 (+)- 68878 Kaempferide 69545 Biacangelicin 77686 Matairesinol 04157 trans-Caffeic acid** 51868 Naringenin 4',7-dimethylether 76716 Camphor (dl)* 02070595 Quercetin 3-glucoside 16654 Camphene 442505 Quercetin dihydrate* 00200595 Chlorogenic acid* 00500590 (−)-α-Santonin 53653 Eucalyptol (1,8-Cineole)** 95656 Artemisia sp. Eucalyptol (1,8-Cineole)* 00020590 Artemisinin 69532 Eucalyptol (1,8-Cineole) 29210 (−)-α-Bisabolol* 00320188 Eugenol** 79891 (−)-α-Bisabolol 95426 Eugenol* 01050595 (+)-Borneol 68878 Eugenol 35995 (−)-Bornyl acetate 45855 trans-Ferulic acid** 52229 Camphor (dl)* 02070595 Fumaric acid** 76635 Camphene 442505 8-Geranyloxypsoralen 40594 Casticin 16382 Hesperidin 50162 Chlorogenic acid* 00500590 Isoimperatorin 68771 67403 Isopimpinellin 61419 Eucalyptol (1,8-Cineole)** 95656 (−)-α-Pinene 80599 Eucalyptol (1,8-Cineole)* 00020590 α-Pinene* 00040590 Eucalyptol (1,8-Cineole) 29210 (+)-β-Pinene 80607 Eupalitin 66324 Psoralen 73633 Isofraxidin 91214 Quercetin 3-glucoside 16654 Matricin 77347 Quercetin dihydrate* 00200595 Naringenin 4',7-dimethylether 76716 Scopoletin 38332 α-Pinene 80599 Umbelliferone 54826 α-Pinene* 00040590 Vanillic acid** 68654 Resorcinol** 53363 Xanthotoxin 56448 Rutin trihydrate 00300590 Arctostaphylos sp. Scopoletin 38332 Arbutin 66468 Sesamin 59867 (+)-Catechin* 03910590 Aspalathus sp. (+)-Catechin 43412 Aspalathin 03520585 Corilagin 75251 Orientin 55736 Ellagic acid 14668 Quercetin 3-glucoside 16654 Gallic acid** 91215 Quercitrin 00740580 Hydroquinone 74347 Asparagus sp. Hyperoside* 00180585 Chelidonic acid 49526 Myricetin 72576 Hyperoside 00180585 Myricitrin 67268 Quercetin 3-glucoside 16654 Protocatechuic acid* 03930590 Rutin trihydrate* 00300590 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Shatavarin IV 30151 Quercetin 3-glucoside 16654 Azadirachta sp. Quercetin dihydrate* 00200595 2’,3’-Dehydrosalannol 80098 Quercitrin* 00740580 Kaempferol* 00550580 Rutin trihydrate* 00300590 Kaempferol 96353 Ursolic acid* 03240595 Quercetin dihydrate* 00200595 Ursolic acid 89797 Bacopa sp. Armoracia sp. Bacopasaponin C 76092 (−)-Sinigrin hydrate 00290 Bacopaside I 56619 Arnica sp. Bacopaside X 42488 Chlorogenic Acid* 00500590 Bacopaside-II 44698 Cynarin 91801 Bacoside A, mixture of Bacoside A3, Bacopaside II, 76091 1,5-Dicaffeoylquinic acid 16917 Bacopaside X and Bacopasaponin C

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

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sh9885_Update Phytopharma Standards Brochure_v1.indd 15 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Bacoside A3 53889 18692 Bacosine 69528 α-Pinene 80599 Apigenin 7-glucoside* 00720585 α-Pinene* 00040590 Apigenin 7-glucoside 44692 Serratol 78689 Genistein 92136 Brassica sp. Kaempferol* 00550580 trans-Ferulic acid** 52229 Kaempferol 96353 Lutein 07168 Luteolin 7-glucoside* 03600585 trans-Sinapic acid 93878 Luteolin 7-glucoside 49968 (−)-Sinigrin hydrate 00290 Quercetin 3-glucoside 16654 Calendula sp. Quercetin dihydrate* 00200595 Allantoin 93791 Rutin trihydrate* 00300590 trans-Caffeic acid** 51868 Scopoletin 38332 trans-p-Coumaric acid 55823 89948 trans-Ferulic acid** 52229 67359 Hyperoside* 00180585 Betula sp. Isorhamnetin 38907 Betulin 92648 Oleanolic acid* 03920590 Betulin 3,28-diacetate 59919 Oleanolic acid 42515 91466 Protocatechuic acid* 03930590 trans-Caffeic acid** 51868 Protocatechuic acid 08992 (+)-Catechin* 03910590 Quercetin 3-glucoside 16654 (+)-Catechin 43412 Quercetin dihydrate* 00200595 Chlorogenic Acid* 00500590 Rutin trihydrate* 00300590 Hyperoside* 00180585 Scopoletin 38332 Lupeol 18692 Umbelliferone 54826 Myricitrin* 02180585 Camellia sp. Myricitrin 67268 Camellia sinensis extract 05495001 Pyrogallol 06931 trans-Caffeic acid** 51868 Quercetin 3-glucuronide* 00310590 Caffeine** 56396 Quercetin 3-O-glucuronid 90733 (+)-Catechin* 03910590 Quercitrin* 00740580 (+)-Catechin 43412 Rutin trihydrate* 00300590 trans-p-Coumaric acid 55823 Salicylic acid** 52341 Epigallocatechin 03960590 73577 (−)-Epigallocatechin* 08108 Vanillic acid** 68654 Gallic acid** 91215 Boerhaavia sp. (−)-Gallocatechin 01388 Boeravinone B 96844 (−)-Gallocatechin gallate 80352 Eupalitin 66324 Theaflavin 55016 Eupalitin 3-Oβ-D-galactopyranoside 89165 Theaflavin monogallate 53963 Boswellia sp. Theaflavin 3,3'-digallate 92223 3-O-Acetyl-β-boswellic acid 49873 PHR1023 3-O-Acetyl-11-keto-β-boswellic acid 74607 sp. 3-O-Acetyl-α-boswellic acid 56208 Hordenine 61207 3-O-Acetylboswellic acid, mixture of α and β 96729 Isovitexin* 01120590 (+)-Borneol 68878 Isovitexin 67135 (−)-Bornyl acetate 45855 Methyl eugenol 04607 β-Boswellic acid 80342 α-Pinene 80599 Boswellic acid, mixture of α and β 63850 α-Pinene* 00040590 α-Boswellic acid 06813 (+)-β-Pinene 80607 (+)-Catechin* 03910590 (delta9) 56296 (+)-Catechin 43412 Trigonelline hydrochloride 61407 Elemolic acid, mixture of α and β 73527 Vitexin* 00840595 β-Elemonic acid 00708 Vitexin 49513 11-Keto- b-boswellic acid 78535

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

16 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 16 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Capsicum sp. Rubiadin 74553 Apigenin* 01760595 Sennoside A* 01870575 Apigenin 42251 Sennoside B* 00530580 12084 Sennosid C 73235 03813 Sennoside D 16383 Esculin hydrate 06212 Chamomilla sp. Isovitexin* 01120590 Apigenin* 01760595 Isovitexin 67135 Apigenin 42251 Luteolin 7-glucoside* 03600585 Apigenin 7-glucoside* 00720585 Luteolin 7-glucoside 49968 Apigenin 7-glucoside 44692 N-Vanillylnonamide 15971 (−)-α-Bisabolol* 00320188 Orientin* 03810585 (−)-α-Bisabolol 95426 Orientin 55736 Bisabolol oxide A* 00630590 Scopoletin 38332 Bisabolol oxide A 59761 Vitexin* 00840595 (+)-Borneol 68878 Vitexin 49513 (−)-Bornyl acetate 45855 Carica sp. trans-Caffeic acid* 51868 Eucalyptol (1,8-Cineole)** 95656 Chamazulen 91595 Eucalyptol (1,8-Cineole)* 00020590 Luteolin* 03880590 Eucalyptol (1,8-Cineole) 29210 Luteolin 72511 Geraniol 48798 Matricin 77347 Carum sp. Quercetin dihydrate* 00200595 Bergapten 69664 Umbelliferone 54826 (−)-Carveol, mixture of isomers 61370 Vanillic acid** 68654 (−)-Carvone* 00290595 Cichorium sp. (+)-Carvone** 79245 trans-Caffeic acid** 51868 (+)-Carvone 22070 88656 Chlorogenic acid* 00500590 ( −)- 06957 Cryptochlorogenic acid 90467 Chlorogenic acid* 00500590 (+)-Dihydrocarvone, mixture of isomers 09164 trans-p-Coumaric acid 55823 (R)-(+)-Limonene 62118 Esculin hydrate 06212 Neochlorogenic acid 91213 trans-Ferulic acid** 52229 Protocatechuic acid* 03930590 Hyperoside* 00180585 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Isorhamnetin 38907 Quercetin 3-glucoside 16654 Kaempferol 3-glucoside 68437 Quercetin dihydrate* 00200595 Quercetin 3-glucoside 16654 Quercetin 3-glucuronide* 00310590 Quercetin 3-glucuronide* 00310590 Quercetin 3-O-glucuronid 90733 Quercetin 3-O-glucuronid 90733 Salicylic acid** 52341 Quercitrin* 00740580 trans-Sinapic acid 93878 Scopoletin 38332 Vanillic acid** 68654 Umbelliferone 54826 Xanthotoxin 56448 Cimicifuga sp. Cassia sp. Friedelin 92187 Aloe-emodin 93938 Kaempferol* 00550580 (+)-Catechin* 03910590 Kaempferol 96353 (+)-Catechin 43412 Cinchona sp. Chrysophanol 01542 Epiquinidine 00998 Dihydrokaempferol 92204 Epiquinine 89457 Emodin 30269 Cinnamomum sp. Isorhamnetin 38907 Quinine** 69311 Kaempferol* 00550580 Benzyl benzoate** 55177 Kaempferol 96353 Benzyl benzoate 68183 Physcion 93893 (+)-Borneol 68878 Rhein 30873 trans-Caffeic acid** 51868

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

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sh9885_Update Phytopharma Standards Brochure_v1.indd 17 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Camphor (dl)* 02070595 p-Cymene** 49679 Camphene 442505 p-Cymene 30039 (−)-trans- 75541 Didymin 38964 (+)-Catechin* 03910590 Dimethyl anthranilate 49919 (+)-Catechin 43412 90985 trans- 06536 61386 trans- 97013 Eleutheroside B 90974 Cinnamyl acetate 42759 6’,7’-Epoxybergamottin 69779 Cinnamyl alcohol 93066 Eriodictyol 89061 m-Coumaric acid 92649 trans, trans-Farnesol 92386 trans-p-Coumaric acid 55823 trans-Ferulic acid** 52229 Coumarin** 72609 Friedelin 92187 Coumarin* 01260595 Geranyl Acetate 45896 Epicatechin* 03940590 8-Geranyloxypsoralen 40594 (−)-Epicatechin 68097 (±)-Hesperetin 51864 Eucalyptol (1,8-Cineole)** 95656 Hesperidin 50162 Eucalyptol (1,8-Cineole)* 00020590 Isoimperatorin 68771 Eucalyptol (1,8-Cineole) 29210 Isopimpinellin 61419 Eugenol** 79891 Isovitexin* 01120590 Eugenol* 01050595 Isovitexin 67135 Eugenol 35995 (R)-(+)-Limonene 62118 trans-Ferulic acid** 52229 Limonin 64081 Kaempferol* 00550580 Linalool** 61706 Kaempferol 96353 Linalool* 00350190 Linalool** 61706 Linalool 51782 Linalool 51782 Linalyl acetate 49599 trans-p-Methoxycinnamaldehyde 61384 Myrcene 64643 Methyl eugenol 04607 (±)-Naringenin 52186 α-Pinene 80599 Naringin 91842 α-Pinene* 00040590 Neohesperidin 40927 Procyanidin B1 19542 trans-Nerolidol 18143 Procyanidin B2 42157 Neryl acetate 46015 Procyanidin C1 50878 92600 Protocatechuic acid* 03930590 Nomilin 77518 Protocatechuic acid 08992 Obacunone 74191 Salicylic acid* 52341 Octanal 52466 trans-Sinapic acid 93878 Poncirin 77536 (+)-α-Terpineol 83073 Sabinene hydrate 96573 Vanillic acid* 68654 trans-Sinapic acid 93878 Citrus sp. 89392 Bergamottin 01338 Synephrine 75256 Bergapten 69664 91004 Bergaptol 62707 Taxifolin** 03890585 (−)-α-Bisabolol* 00320188 Taxifolin 78666 (−)-α-Bisabolol 95426 γ-Terpinene 86476 Biacangelicin 77686 Theophylline PHR1023 trans-Caffeic acid** 51868 Umbelliferone 54826 Caffeine** 56396 (+)- 06808 (−)-Carvone* 00290595 Xanthotoxin 56448 (+)-Carvone** 79245 Coleus sp. (+)-Carvone 22070 Crocetin dialdehyde 18804 (−)-trans-Caryophyllene 75541 1,9-Dideoxyforskolin 92589 Citropten 08941 Forskolin 93049 trans-p-Coumaric acid 55823 Isoforskolin 94597

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

18 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 18 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Commiphora sp. Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 (E)- 68797 Tetrahydrocurcumin 50202 (Z)-Guggulsterone 78251 (S)-ar-Turmerone 42258 Linalool** 61706 Vanillic acid** 68654 Linalool* 00350190 Cynara sp. Linalool 51782 trans-Caffeic acid** 51868 α-Pinene* 80599 Chlorogenic Acid* 00500590 α-Pinene 00040590 Cryptochlorogenic acid 90467 Sesamin 59867 Cynarin 91801 Crataegus sp. 1,5-Dicaffeoylquinic acid 16917 Crataegus spp extract 05095001 Luteolin* 03880590 trans-Caffeic acid** 51868 Luteolin 72511 (+)-Catechin* 03910590 Luteolin 7-glucoside* 03600585 (+)-Catechin 43412 Luteolin 7-glucoside 49968 Chlorogenic Acid* 00500590 Neochlorogenic acid 91213 Epicatechin* 03940590 Rutin trihydrate* 00300590 (−)-Epicatechin 68097 Echinacea sp. Hyperoside* 00180585 Betaine** 30056 Kaempferol* 00550580 (+)-Borneol 68878 Kaempferol 96353 (−)-Bornyl acetate 45855 Luteolin* 03880590 Caftaric acid 88656 Luteolin 72511 ( −)-Chicoric acid 06957 Luteolin 7-glucoside* 03600585 Chlorogenic acid* 00500590 Luteolin 7-glucoside 49968 Cynarin 91801 Oleanolic acid* 03920590 Echinacoside* 01710580 Oleanolic acid 42515 Echinacoside 07538 Procyanidin A2 28660 Kaempferol* 00550580 Procyanidin B1 19542 Kaempferol 96353 Procyanidin C1 50878 Kuromanin chloride (Chrysanthemin) 44689 Rutin trihydrate* 00300590 α-Pinene 80599 Spiraeoside 91802 α-Pinene* 00040590 Ursolic acid* 03240595 Quercetin dihydrate* 00200595 Ursolic acid 89797 Rutin trihydrate* 00300590 Vanillic acid 4-β-D-glucoside 14515 Verbascoside* 00820580 Vitexin* 00840595 Eclipta sp. Vitexin 49513 Eclalbasaponin I 79736 Vitexin 2-O-rhamnoside* 00660585 Eclalbasaponin II 77084 Vitexin 4''-O-glucoside 43907 Eleutherococcus sp. Curcuma sp. trans-Caffeic acid** 51868 (+)-Borneol 68878 Chlorogenic Acid* 00500590 Camphor (dl)* 02070595 Isofraxidin 91214 Camphene 442505 Eleutheroside E 08198 trans-Cinnamic acid 97013 Oleanolic acid* 03920590 trans-p-Coumaric acid 55823 Oleanolic acid 42515 Curcumin* 00280590 Eleutheroside B 90974 Curcumin 08511 Epilobium sp. ( −)-Curcumol 36236 Hyperoside* 00180585 Demethoxycurcumin 90593 Kaempferol* 00550580 Ethyl trans-4-methoxycinnamate 42479 Kaempferol 96353 Eucalyptol (1,8-Cineole)** 95656 Myricetin 72576 Eucalyptol (1,8-Cineole)* 00020590 Myricitrin 67268 Eucalyptol (1,8-Cineole) 29210 Oenothein B 03805 Hexahydrocurcumin 69727 Oleanolic acid* 03920590 Protocatechuic acid* 03930590 Oleanolic acid 42515

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

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sh9885_Update Phytopharma Standards Brochure_v1.indd 19 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Quercetin 3-glucoside 16654 Isorhamnetin 38907 Quercetin dihydrate* 00200595 Kaempferol* 00550580 Quercitrin* 00740580 Kaempferol 96353 Ursolic acid* 03240595 (R)-(+)-Limonene 62118 Ursolic acid 89797 Oleanolic acid* 03920590 Equisetum sp. Oleanolic acid 42515 Apigenin* 01760595 (−)-α-Pinene 80599 Apigenin 42251 α-Pinene* 00040590 Dihydrokaempferol 92204 Protocatechuic acid* 03930590 Kaempferol 3-glucoside 68437 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Luteolin* 03880590 Psoralen 73633 Luteolin 72511 Quercetin 3-glucoside 16654 (±)-Naringenin 52186 Quercetin dihydrate 00200595 Quercetin 3-glucoside 16654 Quercetin 3-glucuronide* 00310590 Taxifolin* 03890585 Quercetin 3-O-glucuronid 90733 Taxifolin 78666 Rutin trihydrate* 00300590 Eucalyptus sp. Scopoletin 38332 Camphor (dl)* 02070595 Umbelliferone 54826 Camphene 442505 Vanillic acid** 68654 (+)-Catechin* 03910590 (+)-Catechin 43412 Xanthotoxin 56448 Ellagic acid 14668 Galium sp. Eucalyptol (1,8-Cineole)** 95656 Apigenin* 01760595 Eucalyptol (1,8-Cineole)* 00020590 Apigenin 42251 Eucalyptol (1,8-Cineole) 29210 trans-Caffeic acid** 51868 Gallic acid* 91215 Chlorogenic Acid* 00500590 Hyperoside* 00180585 Coumarin** 72609 Kaempferol* 00550580 Coumarin* 01260595 Kaempferol 96353 Diosmetin 90985 Myricetin 72576 Gallic acid** 91215 α-Pinene 80599 Hesperidin 50162 α-Pinene* 00040590 Kaempferol* 00550580 Quercetin 3-glucoside 16654 Kaempferol 96353 Quercetin dihydrate* 00200595 Luteolin* 03880590 Quercitrin* 00740580 Luteolin 72511 Rutin trihydrate* 00300590 Myricetin 72576 Sabinene hydrate 96573 Quercetin 3-glucoside 16654 Foeniculum sp. Rubiadin 74553 4-Allylanisole (Estragole) 05818 Rutin trihydrate* 00300590 trans-Anethol 10368 Salicylic acid** 52341 trans-Anethol* 00130595 Scopoletin 38332 p-Anisaldehyde** 43621 Garcinia sp. p-Anisaldehyde 97063 18571 Bergapten 69664 Betulin 92648 trans-Caffeic acid** 51868 (+)-Garcinia acid 44292 Camphor (dl)* 02070595 (−)-Calcium hydroxycitrate tribasic 75450 Camphene 442505 Kuromanin chloride (Chrysanthemin) 44689 Chlorogenic Acid* 00500590 trans-Cinnamic acid 97013 Gentiana sp. 1,5-Dicaffeoylquinic acid 16917 Isoorientin 78109 (+)-Fenchone* 00380590 Isovitexin* 01120590 (+)-Fenchone 46208 Isovitexin 67135 trans-Ferulic acid 52229 Mangiferin 06279 Fumaric acid** 76635 Swertiamarine 90957

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20 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 20 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Ginkgo sp. Genistin 73822 Ginkgo biloba extract 05485001 Glycyrrhizic acid ammonium salt* 01250570 Amentoflavone 18571 Glycyrrhizic acid ammonium salt 91443 Apigenin 7-glucoside* 00720585 38986 Apigenin 7-glucoside 44692 Isorhamnetin 38907 Benzyl alcohol** 39971 Isovitexin* 01120590 Benzyl alcohol 08421 Isovitexin 67135 (−)-Bilobalide 79593 Kaempferol* 00550580 Dihydrokaempferol 92204 Kaempferol 96353 Epicatechin* 03940590 Kaempferol 3-glucoside 68437 (−)-Epicatechin 68097 Lupeol 18692 Epigallocatechin* 03960590 (±)-Naringenin 52186 (−)-Epigallocatechin 08108 Quercetin dihydrate* 00200595 Ginkgolic acid C13:0 49962 Rutin trihydrate* 00300590 Ginkgolic acid C15:1* 02580185 Scopoletin 38332 Ginkgolic acid C17:1* 01390590 Umbelliferone 54826 Ginkgolid A* 00770590 Vitexin* 00840595 Ginkgolid B 94970 Vitexin 49513 Ginkgolide C 18309 Gossypium sp. Ginkgolid J 89556 trans-Caffeic acid** 51868 Ginkgotoxin 89960 (+)-Catechin* 03910590 Isorhamnetin 38907 (+)-Catechin 43412 Kaempferol* 00550580 Chlorogenic acid* 00500590 Kaempferol 96353 Kaempferide 69545 Kaempferol 3-glucoside 68437 Kaempferol* 00550580 Luteolin* 03880590 Kaempferol 96353 Luteolin 72511 Kaempferol 3-glucoside 68437 N-Malonyl-DL-tryptophan 77556 Kuromanin chloride (Chrysanthemin) 44689 Protocatechuic acid* 03930590 Quercitrin* 00740580 Protocatechuic acid 08992 Rutin trihydrate* 00300590 Quercetin 3-glucoside 16654 β-Sitosterol 43623 Quercetin dihydrate* 00200595 β-Sitosterol β-D-glucoside 89851 Quercitrin* 00740580 Gymnema sp. Rutin trihydrate* 00300590 Deacylgymnemic acid 40501 69686 Gymnemangenin 52181 Thymol* 00670590 Hamamelis sp. Thymol 72477 trans-Caffeic acid** 51868 Vanillic acid** 68654 Glycine sp. (+)-Catechin* 03910590 Daidzein 16587 (+)-Catechin 43412 Daidzin 42926 Epigallocatechin gallate* 03970590 Fumaric acid** 76635 (−)-Epigallocatechin gallate 93894 Genistein 92136 Gallic acid** 91215 Genistin 73822 (−)-Gallocatechin 01388 N-Malonyl-DL-tryptophan 77556 Hamamelitannin 04646 β-Sitosterol 43623 Kaempferol* 00550580 β-Sitosterol β-D-glucoside 89851 Kaempferol 96353 Vitexin* 00840595 Kaempferol 3-glucoside 68437 Vitexin 49513 Myricetin 72576 Vitexin 2-O-rhamnoside* 00660585 Myricitrin 67268 Glycyrrhiza sp. Quercetin 3-glucoside 16654 Betulinic acid 91466 Quercetin dihydrate* 00200595 Docosyl caffeate 40971 Quercitrin* 00740580 Genistein 92136 Spiraeoside 91802

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sh9885_Update Phytopharma Standards Brochure_v1.indd 21 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Harpagophytum sp. (+)-Catechin* 03910590 Harpagophytum procumbens extract 05125001 (+)-Catechin 43412 Harpagoside* 00420580 Chlorogenic Acid* 00500590 Verbascoside* 00820580 Hypericin* 00190585 Hedera sp. Hyperoside* 00180585 trans-Caffeic acid** 51868 Kaempferol* 00550580 Chlorogenic acid* 00500590 Kaempferol 96353 trans-p-Coumaric acid 55823 Luteolin* 03880590 trans-Ferulic acid 52229 Luteolin 72511 Hederacoside C* 00930585 Luteolin 7-glucoside* 03600585 Hederacoside C 79737 Luteolin 7-glucoside 49968 α-Hederin* 01240585 Mangiferin 06279 α-Hederin 07512 Myricetin 72576 Oleanolic acid* 03920590 Orientin* 03810585 Oleanolic acid 42515 Orientin 55736 Quercetin 3-glucoside 16654 Oxybenzone 59647 Rutin trihydrate* 00300590 Procyanidin B2 42157 Apigenin 7-glucoside* 00720585 Quercetin 3-glucoside 16654 Humulus sp. Quercetin dihydrate 00200595 Apigenin 7-glucoside 44692 Quercitrin 00740580 trans-Caffeic acid** 51868 Illicium sp. Chlorogenic Acid* 00500590 4-Allylanisole (Estragole) 05818 trans-p-Coumaric acid 55823 trans-Anethol 10368 Epicatechin* 03940590 trans-Anethol* 00130595 (−)-Epicatechin 68097 p-Anisaldehyde** 43621 trans-Ferulic acid** 52229 p-Anisaldehyde 97063 Gallic acid** 91215 Anisatin 80478 Hulupinic acid* 01090595 trans-Caffeic acid** 51868 α-Humulene 12448 (+)-Catechin* 03910590 55423 (+)-Catechin 43412 Kaempferol 3-glucoside 68437 1,4-Cineole 27393 Luteolin 7-glucoside* 03600585 trans-p-Coumaric acid 55823 Luteolin 7-glucoside 49968 Epicatechin* 03940590 2-Methyl-3-buten-2-ol 05392 (−)-Epicatechin 68097 Neochlorogenic acid 91213 Epigallocatechin* 03960590 6-Prenylnaringenin 75602 (−)-Epigallocatechin 08108 8-Prenylnaringenin 75119 (+)-Fenchone 00380590 Protocatechuic acid* 03930590 (+)-Fenchone 46208 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 trans-Ferulic acid** 52229 Quercetin 3-glucoside 16654 Hyperoside* 00180585 Rutin trihydrate* 00300590 Kaempferol 3-glucoside 68437 Vanillic acid** 68654 Linalool** 61706 Vitexin* 00840595 Linalool* 00350190 Vitexin 49513 Linalool 51782 Xanthohumol 01130595 Methyl eugenol 04607 Huperzia sp. Protocatechuic acid* 03930590 (−)-Huperzine A 42643 Protocatechuic acid 08992 Hypericum sp. Quercetin 3-glucoside 16654 Hypericum perforatum extract 05295001 Quercitrin* 00740580 Amentoflavone 18571 Rutin trihydrate* 00300590 Apigenin 7-glucoside* 00720585 Shikimic acid 69686 Apigenin 7-glucoside 44692 (+)-α-Terpineol 83073 Avicularin 44006 Vanillic acid** 68654 I3,II8-Biapigenin 73962

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

22 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 22 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Justicia sp. Magnolia sp. Vanillic acid** 68654 (−)-Bornyl acetate 45855 Vasicine 92951 Camphene 442505 Lagerstroemia sp. Eucalyptol (1,8-Cineole)** 95656 Eucalyptol (1,8-Cineole)* 00020590 Corosolic acid 89067 Eucalyptol (1,8-Cineole) 29210 3-O-Methylellagic acid 93026 42612 Lavandula sp. α-Pinene 80599 Betulinic acid 91466 α-Pinene* 00040590 (+)-Borneol 68878 (+)-β-Pinene 80607 trans-Caffeic acid** 51868 Sesamin 59867 Camphor (dl)* 02070595 (+)-α-Terpineol 83073 Camphene 442505 Malus sp. Coumarin** 72609 trans-Caffeic acid** 51868 Coumarin* 01260595 (+)-Catechin* 03910590 Eucalyptol (1,8-Cineole)** 95656 (+)-Catechin 43412 Eucalyptol (1,8-Cineole)* 00020590 trans-p-Coumaric acid 55823 Epicatechin* 03940590 Eucalyptol (1,8-Cineole) 29210 (−)-Epicatechin 68097 trans- 05407 (−)-Gallocatechin 01388 Lavandulol 42583 Hyperoside* 00180585 (R)-(+)-Limonene 62118 91897 Linalool** 61706 Phloridzin dihydrate 79589 Linalool* 00350190 Procyanidin B1 19542 Linalool 51782 Procyanidin B2 42157 Linalyl acetate 49599 Procyanidin C1 50878 Lupeol 18692 Quercetin 3-glucoside 16654 Luteolin* 03880590 Quercetin dihydrate* 00200595 Luteolin 72511 Quercitrin* 00740580 3-Octanone 46214 Rutin trihydrate* 00300590 Oleanolic acid* 03920590 Mangifera sp. Iriflophenone 3-C-β-D-glucopyranoside 91627 Oleanolic acid 42515 3β- 75934 (+)-β-Pinene 80607 Matricaria sp. Protocatechuic acid* 03930590 Apigenin* 01760595 Protocatechuic acid 08992 Apigenin 42251 Rosmarinic acid* 00390580 (−)-α-Bisabolol* 00320188 trans-Sinapic acid 93878 (−)-α-Bisabolol 95426 Terpinen 4-ol* 03900590 Chamazulen 91595 (−)-Terpinen-4-ol 49598 Luteolin* 03880590 (+)-α-Terpineol 83073 Luteolin 72511 Umbelliferone 54826 Matricin 77347 Ursolic acid* 03240595 Melilotus sp. Ursolic acid 89797 (+)-Borneol 68878 (−)-Bornyl acetate 45855 Vanillic acid** 68654 trans-p-Coumaric acid 55823 Vitexin 00840595 Coumarin** 72609 Vitexin 49513 Coumarin* 01260595 Lycium sp. Protocatechuic acid* 03930590 Kaempferol* 00550580 Protocatechuic acid 08992 Kaempferol 96353 Salicylic acid* 52341 Quercetin dihydrate* 00200595 Scopoletin 38332 Rutin trihydrate* 00300590 trans-Sinapic acid 93878 Scopoletin 38332 (+)-α-Terpineol 83073 Vanillic acid** 68654 Thujone Standard Mixture 04314 Withanolide A 74776 Umbelliferone 54826 Withanolide B 94284 Vanillic acid** 68654

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sh9885_Update Phytopharma Standards Brochure_v1.indd 23 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Melissa sp. Luteolin 7-glucoside* 03600585 Apigenin 7-glucoside* 00720585 Luteolin 7-glucoside 49968 Apigenin 7-glucoside 44692 (+)-Menthofuran* 04580595 Betulinic acid 91466 (+)-Menthofuran 63661 trans-Caffeic acid** 51868 (−)-Menthol 00580590 (−)-trans-Caryophyllene 75541 (−)-Menthol 63660 Chlorogenic Acid* 00500590 (−)-Menthone 63677 (±)-Citronellal 72638 (1R)-(−)-Menthyl acetate 45985 trans-p-Coumaric acid 55823 (+)-Pulegone* 04620590 trans-Ferulic acid** 52229 (+)-Pulegone 82569 Geraniol 48798 Rosmarinic acid* 00390580 Luteolin 7-glucoside* 03600585 (+)-α-Terpineol 83073 Luteolin 7-glucoside 49968 Ursolic acid* 03240595 Oleanolic acid* 03920590 Ursolic acid 89797 Oleanolic acid 42515 Momordica sp. Protocatechuic acid* 03930590 Vicine 78260 Protocatechuic acid 08992 Murraya sp. Quercetin 3-glucoside 16654 Koenigicine 94500 Rosmarinic acid* 00390580 Koenimbine 41096 Salicylic acid** 52341 Mahanimbine 77875 trans-Sinapic acid* 93878 Myristica sp. Ursolic acid 03240595 (+)-Borneol 68878 Ursolic acid 89797 Kaempferol* 00550580 Vanillic acid** 68654 Kaempferol 96353 sp. (R)-(+)-Limonene 62118 Apigenin* 01760595 Myristicin 09237 Apigenin 42251 (−)-α-Pinene 80599 Apigenin 7-glucoside* 00720585 α-Pinene* 00040590 Apigenin 7-glucoside 44692 (+)-β-Pinene 80607 trans-Caffeic acid* 51868 Sabinene hydrate 96573 Camphor (dl)* 02070595 Terpinen 4-ol* 03900590 Camphene 442505 (−)-Terpinen-4-ol 49598 (+)-Carvone** 79245 γ-Terpinene 86476 (−)-Carvone* 00290595 (+)-α-Terpineol 83073 (−)-Carvone 22060 Myroxylon sp. (+)-Carvone 22070 Benzyl cinnamate 69139 trans-p-Coumaric acid 55823 Methyl trans-cinnamate 75032 Diosmetin 90985 Nerium sp. Diosmin 61386 Betulin 92648 Eriocitrin 94113 Betulinic acid 91466 Eriodictyol 89061 Oleandrin 06069 Eucalyptol (1,8-Cineole)** 95656 Oleanolic acid* 03920590 Eucalyptol (1,8-Cineole)* 00020590 Oleanolic acid 42515 Eucalyptol (1,8-Cineole) 29210 Rutin trihydrate* 00300590 trans-Ferulic acid** 52229 Ursolic acid* 03240595 Geraniol 48798 Ursolic acid 89797 Hesperidin 50162 Ocimum sp. (1S,2R,5R)-(+)-Isomenthol 59802 Apigenin* 01760595 (−)-Isopulegol* 04570595 Apigenin 42251 (−)-Isopulegol 59770 Cirsilineol 67403 Jasmon 59975 Eucalyptol (1,8-Cineole)** 95656 (R)-(+)-Limonene 62118 Eucalyptol (1,8-Cineole)* 00020590 Luteolin* 03880590 Eucalyptol (1,8-Cineole) 29210 Luteolin 72511 Isoeugenol 34038

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24 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 24 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Methyl eugenol 04607 Vanillin** 30304 Orientin* 03810585 Vitexin* 00840595 Orientin 55736 Vitexin 49513 Ursolic acid* 03240595 Paeonia sp. Ursolic acid 89797 Apigenin 7-glucoside* 00720585 Olea sp. Apigenin 7-glucoside 44692 Apigenin* 01760595 Kaempferol* 00550580 Apigenin 42251 Kaempferol 96353 Apigenin 7-glucoside* 00720585 Kaempferol 3-glucoside 68437 Apigenin 7-glucoside 44692 Paeoniflorin 75603 Betulinic acid 91466 Quercetin dihydrate* 00200595 trans-Caffeic acid* 51868 Panax sp. trans-Cinnamic acid 97013 Panax ginseng extract* 05115001 trans-p-Coumaric acid 55823 Ginsenoside Rb1* 00170580 Esculin hydrate 06212 Ginsenoside Rb2 41868 trans-Ferulic acid** 52229 Ginsenoside Rb3 42635 Kaempferol* 00550580 Ginsenoside Rd 01518 Kaempferol 96353 Ginsenoside Re* 03000590 Luteolin 7-glucoside* 03600585 Ginsenoside Re 77960 Luteolin 7-glucoside 49968 Ginsenoside Rf* 01580590 68594 Ginsenoside Rg1* 00370580 Oleanolic acid* 03920590 Ginsenoside Rg2 08171 Oleanolic acid 42515 Ginsenoside Rg3 64139 Oleuropein 92167 Ginsenoside Rh1 56805 Protocatechuic acid* 03930590 Notoginsenoside R1 77089 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Protopanaxadiol 62685 Quercetin dihydrate* 00200595 Protopanaxatriol 42476 Quercitrin* 00740580 Pseudoginsenoside F11 67530 Rutin trihydrate* 00300590 Vanillic acid** 68654 Scopoletin 38332 Papaver sp. Vanillic acid** 68654 Fumaric acid** 76635 Ononis sp. hydrochloride PHR1182 Apigenin* 01760595 Quercetin 3-glucoside 16654 Apigenin 42251 Vanillic acid** 68654 Apigenin 7-glucoside* 00720585 Passiflora sp. Apigenin 7-glucoside 44692 extract 05085001 trans-Caffeic acid** 51868 Apigenin* 01760595 trans-Cinnamic acid 97013 Apigenin 42251 trans-p-Coumaric acid 55823 95082 trans-Ferulic acid** 52229 Geraniol 48798 Gallic acid** 91215 Isoorientin 78109 Genistein 92136 Hyperoside* 00180585 Hyperoside* 00180585 Isoorientin* 03820585 Kaempferol* 00550580 Isovitexin 01120590 Kaempferol 96353 Isovitexin 67135 Luteolin* 03880590 Oleanolic acid* 03920590 Luteolin 72511 Oleanolic acid 42515 Luteolin 7-glucoside* 03600585 Orientin* 03810585 Luteolin 7-glucoside 49968 Orientin 55736 Myricitrin 67268 Schaftoside 42925 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Scopoletin 38332 Quercetin dihydrate* 00200595 (+)-α-Terpineol 83073 Quercitrin* 00740580 Umbelliferone 54826 Resorcinol** 53363 Rutin trihydrate* 00300590 Vitexin* 00840595 trans-Sinapic acid 93878 Vitexin 49513

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sh9885_Update Phytopharma Standards Brochure_v1.indd 25 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Pelargonium sp. Pinus sp. Umckalin 50792 (+)-Borneol 68878 Peumus sp. (−)-Bornyl acetate 45855 Boldine 67592 Camphene 442505 Phyllanthus sp. (−)-trans-Caryophyllene 75541 Chebulagic acid 69455 (+)-Catechin* 03910590 (+)-Catechin 43412 Friedelin 92187 Chrysin 95082 1-O-Galloyl-β-D-glucose 69288 p-Cymene** 49679 Hypophyllanthin 75142 p-Cymene 30039 Phyllanthin 75110 Dihydrokaempferol 92204 Pimpinella sp. Guaiacol PHR1136 4-Allylanisole (Estragole) 05818 Kaempferol* 00550580 Anethol trans 10368 Kaempferol 96353 Anethol trans* 00130595 (R)-(+)-Limonene 62118 Angelicin 18118 Linalool** 61706 p-Anisaldehyde** 43621 Linalool* 00350190 p-Anisaldehyde 97063 Linalool 51782 Apigenin* 01760595 Myrcene 64643 Apigenin 42251 Myricetin 72576 Apigenin 7-glucoside* 00720585 (−)-α-Pinene 80599 Apigenin 7-glucoside 44692 α-Pinene* 00040590 Bergapten 69664 (+)-β-Pinene 80607 trans-Caffeic acid** 51868 Pinoresinol 06709 Chlorogenic Acid* 00500590 Quercetin 3-glucoside 16654 Quercetin dihydrate* 00200595 Cryptochlorogenic acid 90467 Shikimic acid 69686 (+)-Fenchone* 00380590 Taxifolin* 03890585 (+)-Fenchone 46208 Taxifolin 78666 Fumaric acid** 76635 (+)-α-Terpineol 83073 Isoorientin 78109 Piper sp. Isoorientin* 03820585 4-Allylpyrocatechol 18078 Isopimpinellin 61419 trans-Caffeic acid** 51868 Isovitexin* 01120590 Camphor (dl)* 02070595 Isovitexin 67135 Camphene 442505 Kaempferol* 00550580 trans-Cinnamic acid 97013 Kaempferol 96353 51773 Luteolin* 03880590 (S)-(+)-7,8- 41866 Luteolin 72511 (+)- 52007 Luteolin 7-glucoside* 03600585 Eucalyptol (1,8-Cineole)** 95656 Luteolin 7-glucoside 49968 Eucalyptol (1,8-Cineole)* 00020590 Neochlorogenic acid 91213 Eucalyptol (1,8-Cineole) 29210 Protocatechuic acid* 03930590 trans-Ferulic acid** 52229 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 DL- 59780 Methyl eugenol 04607 Quercetin 3-glucoside 16654 R-(+)- 80488 Quercetin dihydrate* 00200595 Naringenin 4',7-dimethylether 76716 Quercetin 3-glucuronide* 00310590 75047 Quercetin 3-O-glucuronid 90733 Piperyline 55805 Rutin trihydrate* 00300590 Protocatechuic acid* 03930590 Scopoletin 38332 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 (+)-α-Terpineol 83073 Salicylic acid** 52341 Umbelliferone 54826 trans-Sinapic acid 93878 Vanillic acid** 68654 (+)-α-Terpineol 83073 Vanillic acid 4-β-D-glucoside 14515 Vanillic acid** 68654 Xanthotoxin 56448 75575

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26 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 26 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Plantago sp. Quercetin dihydrate* 00200595 Apigenin 7-glucoside* 00720585 Quercetin 3-glucuronide* 00310590 Apigenin 7-glucoside 44692 Quercetin 3-O-glucuronid 90733 Aucubine 55561 Quercitrin* 00740580 trans-Caffeic acid** 51868 Scopoletin 38332 Chlorogenic Acid* 00500590 trans-Sinapic acid 93878 Neochlorogenic acid 91213 Umbelliferone 54826 Verbascoside 00820580 Ursolic acid* 03240595 Polygonum sp. Ursolic acid 89797 Aloe-emodin* 93938 Vanillic acid** 68654 trans-Caffeic acid** 51868 Primula sp. Chlorogenic acid* 00500590 Apigenin* 01760595 Chrysophanol 01542 Apigenin 42251 trans-p-Coumaric acid 55823 trans-Caffeic acid** 51868 Emodin 30269 (+)-Catechin* 03910590 Epicatechin* 03940590 (+)-Catechin 43412 (−)-Epicatechin 68097 Epicatechin 03940590 Epicatechin 3-gallate (-)* 03950590 (−)-Epicatechin 68097 Gallic acid* 91215 Epigallocatechin* 03960590 Hyperoside* 00180585 (−)-Epigallocatechin 08108 Isovitexin* 01120590 Isorhamnetin 38907 Isovitexin 67135 Kaempferol* 00550580 Luteolin* 03880590 Kaempferol 96353 Luteolin 72511 Kaempferol 3-glucoside 68437 Physcion 93893 Myricetin 72576 Quercitrin* 00740580 chloride 04288 trans-Resveratrol** 76511 Primulaverin 30147 Rhein 30873 Primverin 90657 Scopoletin 38332 Quercetin 3-glucoside 16654 Umbelliferone 54826 Quercetin dihydrate* 00200595 Vitexin* 00840595 Rutin trihydrate* 00300590 Vitexin 49513 Psoralea sp. Potentilla sp. Bakuchicin 75747 trans-Caffeic acid** 51868 Bakuchiol 68612 (+)-Catechin* 03910590 Pueraria sp. (+)-Catechin 43412 Daidzein 16587 Chlorogenic Acid* 00500590 Daidzin 42926 trans-p-Coumaric acid 55823 96006 Coumarin** 72609 Tectoridin 89948 Coumarin* 01260595 Tectorigenin 67359 3-O-rutinoside chloride (Keracyanin chloride) 36428 Punica sp. Ellagic acid 14668 Asiatic acid 89773 Epigallocatechin* 03960590 Asiaticoside 43191 (−)-Epigallocatechin 08108 Betulinic acid 91466 trans-Ferulic acid** 52229 Chlorogenic acid* 00500590 Gallic acid** 91215 Corilagin 75251 (−)-Gallocatechin 01388 trans-p-Coumaric acid 55823 trans-Isoferulic acid 05407 3-O-β-D-glucoside chloride 73705 Kaempferol* 00550580 Ellagic acid 14668 Kaempferol 96353 Gallic acid** 91215 Kuromanin chloride (Chrysanthemin) 44689 Kuromanin chloride (Chrysanthemin) 44689 Myricetin 72576 Neochlorogenic acid 91213 Protocatechuic acid* 03930590 Protocatechuic acid* 03930590 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

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sh9885_Update Phytopharma Standards Brochure_v1.indd 27 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Punicalagin 50793 Sennoside A* 01870575 Punicalin, mixture of anomers 67988 Sennoside B* 00530580 Ursolic acid* 03240595 Rosmarinus sp. Ursolic acid 89797 Betulin 92648 Quercus sp. (+)-Borneol 68878 Betulin 92648 (−)-Bornyl acetate 45855 (+)-Catechin* 03910590 trans-Caffeic acid** 51868 (+)-Catechin 43412 Camphor (dl)* 02070595 Epicatechin* 03940590 Camphene 442505 (−)-Epicatechin 68097 Carnosic acid 91209 Friedelin 92187 Carnosol (Pikrosalvin) 49702 Gallic acid** 91215 trans-p-Coumaric acid 55823 (−)-Gallocatechin 01388 Cryptotanshinone 80709 Hyperoside* 00180585 p-Cymene** 49679 Lupeol 18692 p-Cymene 30039 Quercetin 3-glucoside 16654 Diosmetin 90985 Quercetin dihydrate* 00200595 Diosmin 61386 Quercitrin* 00740580 Eucalyptol (1,8-Cineole)** 95656 Tiliroside 79257 Eucalyptol (1,8-Cineole)* 00020590 Rhamnus sp. Eucalyptol (1,8-Cineole) 29210 Aloe-emodin 93938 trans-Ferulic acid** 52229 Aloin A 50292 (±)-Hesperetin 51864 Chelidonic acid 49526 Hesperidin 50162 Chrysophanol 01542 (R)-(+)-Limonene 62118 Emodin 30269 Luteolin* 03880590 Frangulin A 61237 Luteolin 72511 Frangulin B 68912 Luteolin 7-glucoside* 03600585 Isorhamnetin 38907 Luteolin 7-glucoside 49968 Kaempferide 69545 Myrcene 64643 Kaempferol* 00550580 Oleanolic acid* 03920590 Kaempferol 96353 Oleanolic acid 42515 Kaempferol 3-glucoside 68437 (−)-α-Pinene 80599 Physcion 93893 α-Pinene* 00040590 Quercetin 3-glucoside 16654 Protocatechuic acid 03930590 Quercetin dihydrate* 00200595 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Rheum sp. Rosmarinic acid* 00390580 Aloe-emodin 93938 trans-Sinapic acid 93878 (+)-Catechin* 03910590 (+)-α-Terpineol 83073 (+)-Catechin 43412 Ursolic acid* 03240595 Chrysophanol 01542 Ursolic acid 89797 trans-p-Coumaric acid 55823 Vanillic acid** 68654 Cyanidin 3-O-rutinoside chloride (Keracyanin chloride) 36428 Salix sp. Emodin 30269 (1S)-(−)-Verbenone 94882 Epicatechin* 03940590 Amentoflavone 18571 (−)-Epicatechin 68097 Apigenin* 01760595 Gallic acid** 91215 Apigenin 42251 (−)-Gallocatechin 01388 (+)-Catechin* 03910590 Kuromanin chloride (Chrysanthemin) 44689 (+)-Catechin 43412 Physcion 93893 Chlorogenic Acid* 00500590 Quercetin 3-glucoside 16654 Dihydrokaempferol 92204 Quercitrin* 00740580 Eleutheroside B 90974 Rhapontin 94168 Epicatechin* 03940590 Rhein 30873 (−)-Epicatechin 68097 Rutin trihydrate* 00300590 Eriodictyol 89061

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

28 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 28 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Hyperoside* 00180585 trans-Sinapic acid 93878 Luteolin* 03880590 Sodium 3-(3,4-dihydroxyphenyl)-DL-lactate 39363 Luteolin 72511 Tanshinone I 80714 Luteolin 7-glucoside* 03600585 Tanshinone II A 51704 Luteolin 7-glucoside 49968 (+)-α-Terpineol 83073 (±)-Naringenin 52186 Thujone Standard Mixture 04314 Neochlorogenic acid 91213 Ursolic acid* 03240595 Picein 74192 Ursolic acid 89797 Procyanidin B1 19542 Sambucus sp. Quercitrin* 00740580 Betulin 92648 D-(−)-Salicin 79588 trans-Caffeic acid** 51868 Salidroside 43866 Chlorogenic Acid* 00500590 Taxifolin* 03890585 trans-p-Coumaric acid 55823 Taxifolin 78666 Cyanidin 3-O-rutinoside chloride (Keracyanin chloride) 36428 Salvia sp. trans-Ferulic acid** 52229 Apigenin* 01760595 Hyperoside* 00180585 Apigenin 42251 Isoquercitrin* 00140585 Apigenin 7-glucoside* 00720585 Kaempferol* 00550580 Apigenin 7-glucoside 44692 Kaempferol 96353 Betulin 92648 Kaempferol 3-glucoside 68437 (+)-Borneol 68878 Kuromanin chloride (Chrysanthemin) 44689 (−)-Bornyl acetate 45855 Lupeol 18692 trans-Caffeic acid** 51868 Oleanolic acid* 03920590 Camphor (dl)* 02070595 Oleanolic acid 42515 Camphene 442505 Quercetin 3-glucoside 16654 Carnosic acid 91209 Quercetin dihydrate* 00200595 Carnosol (Pikrosalvin) 49702 Quercitrin* 00740580 Chlorogenic Acid* 00500590 Rutin trihydrate* 00300590 Eucalyptol (1,8-Cineole)* 00020590 Ursolic acid* 03240595 Cirsilineol 67403 Ursolic acid 89797 trans-p-Coumaric acid 55823 Schisandra sp. Cryptochlorogenic acid 90467 Schizandrin A 90139 Cryptotanshinone 80709 Scrophularia sp. Diosmetin 90985 Aucubine 55561 Eucalyptol (1,8-Cineole) 29210 trans-Caffeic acid** 51868 trans-Ferulic acid** 52229 trans-Cinnamic acid 97013 trans-Isoferulic acid 05407 trans-p-Coumaric acid 55823 (R)-(+)-Limonene 62118 Diosmetin 90985 Linalool 51782 Diosmin 61386 Linalyl acetate 49599 trans-Ferulic acid** 52229 Luteolin* 03880590 Harpagoside* 00420580 Luteolin 72511 Hesperidin 50162 Luteolin 7-glucoside* 03600585 trans-Isoferulic acid 05407 Luteolin 7-glucoside 49968 Protocatechuic acid* 03930590 Neochlorogenic acid 91213 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Oleanolic acid* 03920590 trans-Sinapic acid 93878 Oleanolic acid 42515 Vanillic acid** 68654 (−)-α-Pinene 80599 Senecio sp. α-Pinene* 00040590 Apigenin 7-glucoside* 00720585 (+)-β-Pinene 80607 Apigenin 7-glucoside 44692 Rosmarinic acid* 00390580 (−)-α-Bisabolol* 00320188 Salvianolic acid A 97599 (−)-α-Bisabolol 95426 Salvianolic acid B 49724 Kaempferol 3-glucoside 68437 Sclareol 49944 Quercetin 3-glucoside 16654

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

For more information, visit sigma-aldrich.com/medicinalplants 29

sh9885_Update Phytopharma Standards Brochure_v1.indd 29 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Quercetin dihydrate* 00200595 Quercitrin* 00740580 Quercitrin* 00740580 38462 Rutin trihydrate* 00300590 Rebaudioside B 49747 Senecionine, dried down 37031 Rebaudioside C 30987 Senecionine 50351 Rebaudioside D 19189 Seneciphylline, dried down 37033 Rubusoside 62933 Seneciphylline 73913 Steviol 19345 Senkirkine, dried down 37032 Steviolbioside 59754 Senna sp. Stevioside 50956 Senna extract 05475001 Syzygium sp. Sennoside A* 01870575 Acetyleugenol 04733 Sennoside B* 00530580 80479 Sennosid C 73235 Betulinic acid 91466 Sennoside D 16383 (+)-Borneol 68878 Serenoa sp. (−)-Bornyl acetate 45855 Kaempferol 3-glucoside 68437 trans-Caffeic acid** 51868 Rutin trihydrate* 00300590 Camphor (dl)* 02070595 β-Sitosterol 43623 Camphene 442505 β-Sitosterol β-D-glucoside 89851 (−)-trans-Caryophyllene 75541 Silybum sp. trans-p-Coumaric acid 55823 Silybum marianum extract 05135001 Cryptochlorogenic acid 90467 Apigenin* 01760595 Ellagic acid 14668 Apigenin 42251 Eucalyptol (1,8-Cineole)** 95656 Apigenin 7-glucoside* 00720585 Eucalyptol (1,8-Cineole)* 00020590 Apigenin 7-glucoside 44692 Eucalyptol (1,8-Cineole) 29210 Dihydrokaempferol 92204 Eugenol** 79891 Eriodictyol 89061 Eugenol* 01050595 Fumaric acid* 76635 Eugenol 35995 Isofraxidin 91214 trans-Ferulic acid** 52229 Isosilybin A 97326 Gallic acid** 91215 Isosilybin B 95684 Geraniol 48798 Kaempferide 69545 Guaiacol PHR1136 (±)-Naringenin 52186 Hyperoside* 00180585 Quercetin dihydrate* 00200595 Isoeugenol 34038 Silybin 02000585 Kaempferol* 00550580 Silybin B 59527 Kaempferol 96353 Silychristin 51681 Kaempferol 3-glucoside 68437 Silydianin 30494 Kuromanin chloride (Chrysanthemin) 44689 Taxifolin* 03890585 Methyl eugenol 04607 Taxifolin 78666 Myricetin 72576 Solanum sp. Oleanolic acid* 03920590 trans-Caffeic acid** 51868 Oleanolic acid 42515 trans-p-Coumaric acid 55823 (−)-α-Pinene 80599 Degalactotigonin 92056 α-Pinene* 00040590 N-Malonyl-DL-tryptophan 77556 (+)-β-Pinene 80607 Scopoletin 38332 Protocatechuic acid* 03930590 Umbelliferone 54826 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 sp. Quercetin 3-glucoside 16654 Dulcoside A 90378 Quercetin dihydrate* 00200595 Geraniol 48798 (+)-α-Terpineol 83073 Isosteviol 92273 Vanillic acid** 68654 Luteolin 7-glucoside* 03600585 Tanacetum sp. Luteolin 7-glucoside 49968 Apigenin* 01760595 Quercetin 3-glucoside 16654 Apigenin 42251

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

30 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 30 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Apigenin 7-glucoside* 00720585 Thymus sp. Apigenin 7-glucoside 44692 Apigenin* 01760595 (−)-Bornyl acetate 45855 Apigenin 42251 trans-Caffeic acid** 51868 Apigenin 7-glucoside* 00720585 Camphor (dl)* 02070595 Apigenin 7-glucoside 44692 Camphene 442505 (+)-Borneol 68878 Chamazulen 91595 (−)-Bornyl acetate 45855 Chlorogenic Acid* 00500590 trans-Caffeic acid** 51868 Cirsilineol 67403 Camphor (dl)* 02070595 Diosmetin 90985 Camphene 442505 Eucalyptol (1,8-Cineole)** 95656 Carvacrol 42632 Eucalyptol (1,8-Cineole)* 00020590 Carvacrol 42632 Eucalyptol (1,8-Cineole) 29210 Carvacrol methyl ether 43778 trans-Ferulic acid** 52229 Cirsilineol 67403 Isofraxidin 91214 p-Cymene** 49679 Isorhamnetin 38907 p-Cymene 30039 Linalyl acetate 49599 Dihydrokaempferol 92204 Luteolin* 03880590 Eriocitrin 94113 Luteolin 72511 Eriodictyol 89061 Luteolin 7-glucoside* 03600585 Eucalyptol (1,8-Cineole)** 95656 Luteolin 7-glucoside 49968 Eucalyptol (1,8-Cineole)* 00020590 (±)-Naringenin 52186 Eucalyptol (1,8-Cineole) 29210 Orientin* 03810585 trans-Ferulic acid** 52229 Orientin 55736 Geraniol 48798 (−)-α-Pinene 80599 Linalool** 61706 α-Pinene* 00040590 Linalool* 00350190 (+)-β-Pinene 80607 Linalool 51782 Protocatechuic acid* 03930590 Linalyl acetate 49599 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Luteolin* 03880590 Quercetin dihydrate* 00200595 Luteolin 72511 Scopoletin 38332 Luteolin 7-glucoside* 03600585 Sesamin 59867 Luteolin 7-glucoside 49968 Thymol* 00670590 Myrcene 64643 Thymol 72477 (±)-Naringenin 52186 Terminalia sp. Oleanolic acid* 03920590 Arjunetin 90331 Oleanolic acid 42515 Arjunic acid 06244 (−)-α-Pinene 80599 (+)-Catechin* 03910590 α-Pinene* 00040590 (+)-Catechin 43412 Protocatechuic acid* 03930590 Chebulagic acid 69455 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Corilagin 75251 Rosmarinic acid* 00390580 3,3’-Di-O-methyl ellagic acid 4’-O-β-D-xylopyranoside 90905 Sakuranetin 73422 Ellagic acid 14668 Salicylic acid* 52341 Friedelin 92187 trans-Sinapic acid 93878 Gallic acid** 91215 Taxifolin* 03890585 Kaempferol* 00550580 Taxifolin 78666 Kaempferol 96353 Terpinen 4-ol* 03900590 Naringenin 4',7-dimethylether 76716 (−)-Terpinen-4-ol 49598 Oleanolic acid* 03920590 γ-Terpinene 86476 Oleanolic acid 42515 (+)-α-Terpineol 83073 Punicalagin 50793 Thymol* 00670590 Quercetin dihydrate* 00200595 Thymol 72477 Shikimic acid 69686 Ursolic acid* 03240595 trans-Sinapic acid 93878 Ursolic acid 89797 1,3,6-Tri-O-galloyl-β-D-glucose 78864 Vanillic acid** 68654

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

For more information, visit sigma-aldrich.com/medicinalplants 31

sh9885_Update Phytopharma Standards Brochure_v1.indd 31 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Tilia sp. 3-O-β-D-glucoside chloride 30638 trans-Caffeic acid** 51868 Procyanidin B1 19542 Chlorogenic Acid* 00500590 Procyanidin B2 42157 trans-p-Coumaric acid 55823 Procyanidin C1 50878 Ellagic acid 14668 Protocatechuic acid* 03930590 Esculin hydrate 06212 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Fraxetin 18224 Quercetin 3-glucoside 16654 Fraxin 80533 Quercetin dihydrate* 00200595 Gallic acid** 91215 Quercitrin* 00740580 Hyperoside* 00180585 Salicylic acid* 52341 Isoquercitrin* 00140585 Salidroside 43866 Kaempferol* 00550580 63627 Kaempferol 96353 Ursolic acid* 03240595 Kaempferol 3-glucoside 68437 Ursolic acid 89797 Procyanidin B2 42157 Valeriana sp. Protocatechuic acid* 03930590 Valeriana officinalis extract 05105001 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Acetoxyvalerenic acid 18543 Quercetin 3-glucoside 16654 (+)-Borneol 68878 Quercetin dihydrate* 00200595 (−)-Bornyl acetate 45855 Quercitrin 00740580 trans-Caffeic acid** 51868 Rutin trihydrate* 00300590 Camphor (dl)* 02070595 Tiliroside 79257 Camphene 442505 Tribulus sp. Tribulosin 51675 Chlorogenic acid* 00500590 Triticum sp. Eucalyptol (1,8-Cineole)** 95656 N-Malonyl-DL-tryptophan 77556 Eucalyptol (1,8-Cineole)* 00020590 β-Sitosterol 43623 Eucalyptol (1,8-Cineole) 29210 β-Sitosterol β-D-glucoside 89851 Hesperidin 50162 Urtica sp. Hydroxyvalerenic acid 55507 Oleanolic acid* 03920590 trans-Isoferulic acid 05407 Oleanolic acid 42515 (−)-α-Pinene 80599 β-Sitosterol 43623 α-Pinene* 00040590 Vaccinum sp. (+)-β-Pinene 80607 Arbutin 66468 (+)-α-Terpineol 83073 (+)-Catechin* 03910590 Valerenic acid* 02010595 (+)-Catechin 43412 sp. Chlorogenic Acid* 00500590 Vanillin** 30304 Cyanidin 3-O-α-L-arabinoside chloride 05098 Verbascum sp. Cyanidin 3-galactoside chloride (Idaein chloride) 91635 Apigenin* 01760595 Cyanidin chloride 94099 Apigenin 42251 Delphinidin chloride 14389 Apigenin 7-glucoside* 00720585 Delphinidin 3-O-β-D-galactoside chloride 04301 Apigenin 7-glucoside 44692 Delphinidin 3-O-β-D-glucoside chloride 73705 Aucubine 55561 Epicatechin* 03940590 trans-Caffeic acid** 51868 (−)-Epicatechin 68097 Chlorogenic acid* 00500590 Hyperoside* 00180585 trans-p-Coumaric acid 55823 Kuromanin chloride (Chrysanthemin) 44689 Diosmin 61386 chloride 92607 Eriodictyol 89061 Malvidin 3-galactoside chloride 79311 trans-Ferulic acid** 52229 Myricetin 72576 Harpagoside* 00420580 Oenin chloride 04288 Hesperidin 50162 Oleanolic acid* 03920590 Kaempferol* 00550580 Oleanolic acid 42515 Kaempferol 96353 3-O-glucoside chloride 42008

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

32 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 32 07/07/16 2:29 pm Compound Cat. No. Compound Cat. No. Luteolin* 03880590 Vitis sp. Luteolin 72511 Caftaric acid 88656 Luteolin 7-glucoside* 03600585 (+)-Catechin* 03910590 Luteolin 7-glucoside 49968 (+)-Catechin 43412 Protocatechuic acid* 03930590 Chlorogenic acid* 00500590 trans-p-Coumaric acid 55823 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Delphinidin 3-O-β-D-glucoside chloride 73705 Quercetin dihydrate* 00200595 Epicatechin* 03940590 Rutin trihydrate* 00300590 (−)-Epicatechin 68097 Vanillic acid* 68654 Geraniol 48798 Verbascoside* 00820580 Kuromanin chloride (Chrysanthemin) 44689 Viscum sp. Malvidin chloride 92607 Betulinic acid 91466 Oenin chloride 04288 trans-Caffeic acid** 51868 Oleanolic acid* 03920590 Eleutheroside B 90974 Oleanolic acid 42515 Eleutheroside E 08198 Petunidin 3-O-β-D-glucoside chloride 30638 trans-Ferulic acid** 52229 Procyanidin B1 19542 Isorhamnetin 38907 Procyanidin B2 42157 Oleanolic acid* 03920590 Procyanidin C1 50878 Oleanolic acid 42515 Quercetin 3-glucoside 16654 Protocatechuic acid* 03930590 Quercetin 3-glucuronide* 00310590 Protocatechuic acid (3,4-Dihydroxybenzoic acid) 08992 Quercetin 3-O-glucuronid 90733 Quercetin dihydrate* 00200595 trans-Resveratrol** 76511 Withania sp. Sakuranetin 73422 12-Deoxywithastramonolide 94187 trans-Sinapic acid 93878 β-Sitosterol β-D-glucoside 89851 Ursolic acid* 03240595 Withaferin A 89910 Ursolic acid 89797 Withanolide A 74776 Vanillic acid** 68654 Withanolide B 94284 Vitex sp. Withanone 90896 12274 Withanoside IV 94186 Aucubine 55561 Withanoside V 66042 (−)-Bornyl acetate 45855 Zingiber sp. Casticin 16382 Asarylaldehyde 16219 Eucalyptol (1,8-Cineole)** 95656 (+)-Borneol 68878 Eucalyptol (1,8-Cineole)* 00020590 Camphor (dl)* 02070595 Eucalyptol (1,8-Cineole) 29210 Camphene 442505 Isoorientin 78109 (+)-Carvone** 79245 Isoorientin* 03820585 (−)-Carvone* 00290595 Isovitexin* 01120590 (−)-Carvone 22060 Isovitexin 67135 (+)-Carvone 22070 trans-p-Coumaric acid 55823 Luteolin 7-glucoside* 03600585 Eucalyptol (1,8-Cineole)** 95656 Luteolin 7-glucoside 49968 Eucalyptol (1,8-Cineole)* 00020590 Negundoside 80724 Eucalyptol (1,8-Cineole) 29210 Orientin* 03810585 trans-Ferulic acid** 52229 Orientin 55736 [10]- 42630 (−)-α-Pinene 80599 [6]-Gingerol 50866 α-Pinene* 00040590 [8]-Gingerol 01514 (+)-β-Pinene 80607 Kuromanin chloride (Chrysanthemin) 44689 Ursolic acid* 03240595 Resorcinol* 53363 Ursolic acid 89797 [6]- 39303 Vitexin* 00840595 trans-Sinapic acid 93878 Vitexin 49513 Vanillic acid** 68654

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

For more information, visit sigma-aldrich.com/medicinalplants 33

sh9885_Update Phytopharma Standards Brochure_v1.indd 33 07/07/16 2:29 pm Phytochemical Standards Product List

On the following pages, a complete list of phytochemical standards available through Sigma-Aldrich is shown in alphabetical order. The over 600 products include primary pharmaceutical standards from HWI (*) and TraceCERT® certified reference materials (**).

Description Package Cat. No. Description Package Cat. No. 10 mg 49975 Avicularin 5 mg 44006 Acetoxyvalerenic acid 10 mg 18543 Bacopasaponin C 5 mg 76092 3-O-Acetyl-β-boswellic acid 5 mg 49873 Bacopaside I 5 mg 56619 3-O-Acetyl-11-keto-β-boswellic acid 5 mg 74607 Bacopaside X 5 mg 42488 3-O-Acetyl-α-boswellic acid 5 mg 56208 Bacopaside-II 5 mg 44698 3-O-Acetylboswellic acid, mixture of 5 mg 96729 Bacoside A, mixture of Bacoside A3, 5 mg 76091 α and β Bacopaside II, Bacopaside X and Acetyleugenol 100 mg 04733 Bacopasaponin C Aconitine 10 mg 44787 Bacoside A3 5 mg 53889 Agnuside 10 mg 12274 Bacosine 5 mg 69528 Allantoin 50 mg 93791 Bakuchicin 10 mg 75747 (+)-L-Alliin 10 mg 72805 Bakuchiol 10 mg 68612 4-Allylanisole (Estragole) 1 mL, 5 mL 05818 Benzyl alcohol** 100 mg 39971 4-Allylpyrocatechol 10 mg 18078 Benzyl alcohol 5 mL, 25 mL 08421 Aloe-emodin 10 mg 93938 Benzyl benzoate** 1 mL 55177 Aloenin A 10 mg 41757 Benzyl benzoate 1 mL 68183 Aloin A 10 mg 50292 Benzyl cinnamate 100 mg 69139 Amentoflavone 10 mg 18571 Bergamottin 5 mg 01338 (15:0)-Anacardic acid 10 mg 05506 Bergapten 25 mg 69664 Andrograpanin 5 mg 19443 Bergaptol 10 mg 62707 Andrographolide 5 mg 90281 Bergenin 10 mg 80479 trans-Anethol* 100 mg 00130595 Betaine** 50 mg 30056 trans-Anethol 1 mL, 5 mL 10368 Betulin 50 mg 92648 Angelicin 10 mg 18118 Betulin 3, 28-diacetate 25 mg 59919 p-Anisaldehyde** 100 mg 43621 Betulinic acid 10 mg 91466 p-Anisaldehyde* 50 mg 05320590 Biacangelicin 10 mg 77686 p-Anisaldehyde 1 mL, 5 mL 97063 I3,II8-Biapigenin 10 mg 73962 Anisatin 10 mg 80478 Bilobalide* 10 mg 00760595 Apigenin 10 mg 01760595 (−)-Bilobalide 10 mg 79593 Apigenin 10 mg 42251 Biotin** 50 mg 91827 Apigenin-6,8-diglucoside (Vicenin 2)* 10 mg 03980585 (−)-α-Bisabolol* 100 mg 00320188 Apigenin 7-glucoside* 10 mg 00720585 (−)-α-Bisabolol 1 mL 95426 Apigenin 7-glucoside 5 mg, 25 mg 44692 Bisabolol oxide A* 25 mg 00630590 Apigenin 7-O-glucuronide* 10 mg 04490590 Bisabolol oxide A 10 mg 59761 Arbutin 50 mg 66468 Boeravinone B 10 mg 96844 Arbutin* 50 mg 00890590 Boldine 100 mg 67592 Arjunetin 5 mg 90331 (+)-Borneol 10 mg 68878 Arjunic acid 5 mg 06244 (−)-Bornyl acetate* 50 mg 00400585 Artemisinin 10 mg 69532 (−)-Bornyl acetate 1 mL, 5 mL 45855 β-Asarone* 25 mg 02890590 α-Boswellic acid 10 mg 06813 Asarylaldehyde 50 mg 16219 β-Boswellic acid 5 mg 80342 L-Ascorbic acid** 100 mg 57803 Boswellic acid, mixture of α and β 5 mg 63850 Asiatic acid 10 mg 89773 Butein 10 mg 72795 Asiaticoside* 10 mg 04560590 trans-Caffeic acid** 50 mg 51868 Asiaticoside 1 mg, 5 mg 43191 Caffeine** 100 mg 56396 Aspalathin* 10 mg 03520585 Caftaric acid 10 mg 88656 Aspidinol 10 mg 55659 Camellia sinensis extract 150 mg 05495001 Aucubin* 25 mg 00090590 Camphene* 100 mg 01410590 Aucubine 5 mg, 25 mg 55561 Camphor (dl)* 100 mg 02070595

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

34 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 34 07/07/16 2:29 pm Description Package Cat. No. Description Package Cat. No. Camphene 1000 mg 442505 Crocetin dialdehyde 10 mg 18804 Capsaicin 10 mg, 50 mg 12084 Cryptochlorogenic acid 5 mg 90467 Cardanol 50 mg 04016 Cryptotanshinone 10 mg 80709 (+)-3-δ-Carene* 100 mg 00410590 Curcumin* 10 mg 00280590 Carnosic acid* 10 mg 05330590 Curcumin 10 mg 08511 Carnosic acid 5 mg 91209 ( −)-Curcumol 10 mg 36236 Carnosol (Pikrosalvin) 10 mg 49702 Cyanidin 3-O-α-L-arabinoside chloride 10 mg 05098 Carvacrol 50 mg 42632 Cyanidin chloride 10 mg 94099 Carvacrol* 50 mg 04270590 Cyanidin 3-galactoside chloride 10 mg 91635 Carvacrol methyl ether 50 mg 43778 (Idaein chloride) (−)-Carveol, mixture of isomers 50 mg 61370 Cyanidin 3-O-rutinoside chloride 1 mg, 5 mg 36428 (Keracyanin chloride) (−)-Carvone* 100 mg 00290595 Cyanidin-3-sambubiosidchlorid 5 mg 43046 (+)-Carvone** 100 mg 79245 Cyanidin-3-sophorosidchlorid 5 mg 42739 (−)-Carvone 1 mL, 5 mL 22060 Cycloolivil 10 mg 56523 (+)-Carvone 1 mL 22070 p-Cymene 5 mL 30039 (−)-trans-Caryophyllene 1 mL 75541 p-Cymene** 100 mg 49679 Castalagin 10 mg 61221 Cynarin 5 mg 91801 Casticin 10 mg 16382 Daidzein* 50 mg 05340590 Casticin* 10 mg 01940590 Daidzein 10 mg 16587 (+)-Catechin* 10 mg 03910590 Daidzin* 10 mg 05370590 (+)-Catechin 10 mg 43412 Daidzin 10 mg 42926 Catechin 5-O-gallate 10 mg 89106 Deacylgymnemic acid 5 mg 40501 Chamazulen 20 mg 91595 Degalactotigonin 10 mg 92056 Chebulagic acid 10 mg 69455 Dehydrocostus lactone 10 mg 42575 Chebulinic acid 10 mg 40820 2’,3’-Dehydrosalannol 10 mg 80098 Chelidonic acid 100 mg 49526 Delphinidin chloride 10 mg 14389 ( −)-Chicoric acid 10 mg 06957 Delphinidin 3-O-β-D-galactoside chloride 10 mg 04301 Chlorogenic acid* 25 mg 00500590 Delphinidin 3-O-β-D-glucoside chloride 10 mg 73705 Chrysanthemin (Kuromanin chloride) 5 mg 44689 Delphinidin-3-sambubioside chloride 5 mg 42883 Chrysin 50 mg 95082 Demethoxycurcumin 10 mg 90593 Chrysophanol 25 mg 01542 14-Deoxy-11,12-didehydroandrographolide 5 mg 55549 2CR-Cinchonin 50 mg 30729 12-Deoxywithastramonolide 10 mg 94187 1,4-Cineole 1 mL, 5 mL 27393 Desmethoxyyangonin 5 mg 51773 1,8-Cineole (Eucalyptol)** 100 mg 95656 1,5-Dicaffeoylquinic acid 5 mg 16917 1,8-Cineole (Eucalyptol)* 100 mg 00020590 1,9-Dideoxyforskolin 10 mg 92589 1,8-Cineole (Eucalyptol) 1 mL 29210 Didymin 10 mg 38964 trans-Cinnamaldehyde 50 mg 06536 Digoxin** 50 mg 04599 trans-Cinnamic acid 50 mg 97013 Dihydrocapsaicin 5 mg 03813 Cinnamyl acetate 1 mL 42759 (+)-Dihydrocarvone, mixture of isomers 50 mg 09164 Cinnamyl alcohol 50 mg 93066 Dihydrokaempferol 5 mg 92204 Cirsilineol 5 mg 67403 (S)-(+)-7,8-Dihydrokavain 5 mg 41866 Citral 1 mL 43318 (+)-Dihydromethysticin 5 mg 52007 Citric acid** 100 mg 94676 Dihydromyricetin 10 mg 42866 (±)-Citronellal 1 mL 72638 (-)-Dihydroquinine 50 mg 11532 Citropten 100 mg 08941 Dimethyl anthranilate 1 mL 49919 Coptisin chloride 10 mg 39273 Dimethylpropiothetin hydrochloride 100 mg 80828 Corilagin 10 mg 75251 3,3'-Di-O-methylellagic acid 10 mg 90905 Corosolic acid 10 mg 89067 4'-xylopyranoside m-Coumaric acid 10 mg 92649 Diosmetin 10 mg 90985 p-Coumaric acid* 50 mg 03200595 Diosmin 50 mg 61386 trans-p-Coumaric acid 50 mg 55823 Docosyl caffeate 10 mg 40971 Coumarin* 50 mg 01260595 Dulcoside A 10 mg 90378 Coumarin** 100 mg 72609 Echinacoside* 10 mg 01710580 Crataegus spp extract 150 mg 05095001 Echinacoside 10 mg 07538

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

For more information, visit sigma-aldrich.com/medicinalplants 35

sh9885_Update Phytopharma Standards Brochure_v1.indd 35 07/07/16 2:29 pm Description Package Cat. No. Description Package Cat. No. Eclalbasaponin I 10 mg 79736 Genistin 10 mg 73822 Eclalbasaponin II 10 mg 77084 10 mg 42734 (−)-β-Elemene 25 mg 63965 Geraniol 1 mL, 5 mL 48798 Elemolic acid, mixture of α and β 5 mg 73527 Geranyl Acetate 1 mL 45896 β-Elemonic acid 5 mg 00708 Geranyl acetate* 100 mg 01290190 Eleutheroside B (Syringin) 10 mg 90974 8-Geranyloxypsoralen 10 mg 40594 Ellagic acid* 50 mg 05350590 Germacron 10 mg 42924 Ellagic acid 50 mg 14668 [10]-Gingerol 10 mg 42630 Emodin 10 mg 30269 [6]-Gingerol 10 mg 50866 Epicatechin* 10 mg 03940590 [8]-Gingerol 10 mg 01514 (−)-Epicatechin 10 mg 68097 Ginkgo biloba extract 150 mg 05485001 (−)-Epicatechin 3-gallate* 10 mg 03950590 Ginkgolic acid C13:0 10 mg 49962 Epigallocatechin* 10 mg 03960590 Ginkgolic acid C15:1* 10 mg 02580185 (−)-Epigallocatechin 1 mg 08108 Ginkgolic acid C17:1* 10 mg 01390590 Epigallocatechin gallate* 10 mg 03970590 Ginkgolid A* 25 mg 00770590 (−)-Epigallocatechin gallate 10 mg 93894 Ginkgolid B 10 mg 94970 Epiquinidine 50 mg 00998 Ginkgolide C 10 mg 18309 Epiquinine 50 mg 89457 Ginkgolid J 5 mg 89556 6’,7’-Epoxybergamottin 10 mg 69779 Ginkgotoxin 10 mg 89960 Eriocitrin 5 mg 94113 Ginkgolide C* 25 mg 01490590 Eriocitrin* 10 mg 02660590 Ginsenoside R0 10 mg 94381 Eriodictyol 10 mg 89061 Ginsenoside Rb1* 10 mg 00170580 Esculin hydrate 100 mg 06212 Ginsenoside Rb2 10 mg 41868 Estragole (4-Allylanisole) 1 mL, 5 mL 05818 Ginsenoside Rb3 10 mg 42635 Ethyl trans-4-methoxycinnamate 10 mg 42479 Ginsenoside Rc 5 mg 44987 Eucalyptol (1,8-Cineole)** 100 mg 95656 Ginsenoside Rd 10 mg 01518 Eucalyptol (1,8-Cineole)* 100 mg 00020590 Ginsenoside Re* 10 mg 03000590 Eucalyptol (1,8-Cineole) 1 mL 29210 Ginsenoside Re* 10 mg 77960 Eugenol** 100 mg 79891 Ginsenoside Rf* 10 mg 01580590 Eugenol* 100 mg 01050595 Ginsenoside Rg1* 10 mg 00370580 Eugenol 250 mg 35995 Ginsenoside Rg2 10 mg 08171 Eupalitin 10 mg 66324 Ginsenoside Rg3 10 mg 64139 Eupalitin 3-Oβ-D-galactopyranoside 10 mg 89165 Ginsenoside Rg6 5 mg 43019 Eupatorin 10 mg 52559 Ginsenoside Rh1 10 mg 56805 trans, trans-Farnesol 100 mg 92386 Ginsenoside Rh3 5 mg 43084 (+)-Fenchone* 100 mg 00380590 Ginsenoside Rh4 5 mg 42776 (+)-Fenchone 1 mL, 5 mL 46208 Glutaric acid** 100 mg 89147 trans-Ferulic acid** 50 mg 52229 Glycolic acid** 100 mg 94815 50 mg 94334 10 mg 43534 Forskolin 10 mg 93049 Glycyrrhizic acid ammonium salt* 50 mg 01250570 Frangulin A 10 mg 61237 Glycyrrhizic acid ammonium salt 10 mg 91443 Frangulin B 10 mg 68912 Guaiacol 1.5g PHR1136 Fraxetin 50 mg 18224 Guajaverin 5 mg 94821 Fraxin 10 mg 80533 (E)-Guggulsterone 10 mg 68797 Friedelin 10 mg 92187 (Z)-Guggulsterone 10 mg 78251 Fumaric acid** 100 mg 76635 Gymnemangenin 5 mg 52181 Gallic acid** 100 mg 91215 Hamamelitannin 5 mg 04646 (−)-Gallocatechin 10 mg 01388 Harpagophytum procumbens extract 150 mg 05125001 (−)-Gallocatechin gallate 10 mg 80352 Harpagoside* 25 mg 00420580 1-O-Galloyl-β-D-glucose 10 mg 69288 Hederacoside C* 10 mg 00930585 (+)-Garcinia acid 10 mg 44292 Hederacoside C 10 mg 79737 Genistein* 50 mg 05360590 α-Hederin* 10 mg 01240585 Genistein 10 mg 92136 α-Hederin 10 mg 07512 Genistin* 25 mg 05380590 Herniarin* 10 mg 02250595

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

36 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 36 07/07/16 2:29 pm Description Package Cat. No. Description Package Cat. No. (±)-Hesperetin 50 mg 51864 DL-Kavain 500 mg 59780 Hesperidin* 25 mg 04650590 Keracyanin chloride (Cyanidin 1 mg, 5 mg 36428 Hesperidin 10 mg 50162 3-O-rutinoside chloride) Hexahydrocurcumin 10 mg 69727 11-Keto- b-boswellic acid 5 mg 78535 Isoorientin 5 mg 78109 Khellin 100 mg 00899 Honokiol 25 mg 42612 Koenigicine 10 mg 94500 Hordenine 50 mg 61207 Koenimbine 10 mg 41096 Kuromanin chloride (Chrysanthemin) 5 mg 44689 Hulupinic acid* 10 mg 01090595 Larixylacetat* 50 mg 02730595 α-Humulene 250 mg 12448 Lavandulol 50 mg 42583 (−)-Huperzine A 25 mg 42643 (R)-(+)-Limonene* 100 mg 00590590 Hydroquinone 100 mg 74347 (R)-(+)-Limonene 1 mL, 5 mL 62118 (−)-Calcium hydroxycitrate tribasic 10 mg 75450 Limonin 10 mg 64081 Hydroxyvalerenic acid 5 mg 55507 Linalool** 50 mg 61706 Hypericin* 10 mg 00190585 Linalool* 100 mg 00350190 Hypericum perforatum extract 150 mg 05295001 Linalool 1 mL 51782 Hyperoside* 25 mg 00180585 Linalyl acetate 100 mg 49599 dicyclohexylammonium salt 5 mg 42891 Eleutheroside E 10 mg 08198 Hypophyllanthin 10 mg 75142 Lupeol 10 mg 18692 25 mg 56601 Lutein 1 mg, 5 mg 07168 Idaein chloride 10 mg 91635 Luteolin* 25 mg 03880590 (Cyanidin 3-galactoside chloride) Luteolin 10 mg 72511 Imperatorin (Marmelosin) 10 mg 55193 Luteolin 7-glucoside* 10 mg 03600585 Iriflophenone 3-C-β-D-glucopyranoside 10 mg 91627 Luteolin 7-glucoside 10 mg 49968 (+)-Isocorydin 10 mg 42899 Luteolin-7-O-β-D-glucuronide* 10 mg 04480585 Isoeugenol 5 mL 34038 Magnesium L-lactate hydrate** 100 mg 40394 trans-Isoferulic acid 10 mg 05407 Mahanimbine 10 mg 77875 Isoforskolin 10 mg 94597 L-(−)-Malic acid** 100 mg 09172 Isofraxidin 5 mg 91214 Malonic acid** 100 mg 68714 Isoimperatorin 10 mg 68771 N-Malonyl-DL-tryptophan 10 mg 77556 Isoliquiritigenin 50 mg 38986 Malvidin chloride 10 mg 92607 (1S,2R,5R)-(+)-Isomenthol* 25 mg 04280590 Malvidin 3-galactoside chloride 1 mg 79311 (1S,2R,5R)-(+)-Isomenthol 25 mg 59802 Mangiferin 10 mg 06279 Isoorientin* 10 mg 03820585 Marmelosin (Imperatorin) 10 mg 55193 Isopimpinellin 10 mg 61419 Maslinic acid 5 mg 68594 (−)-Isopulegol* 50 mg 04570595 Matairesinol 5 mg 04157 (−)-Isopulegol 5 mL 59770 Matricin 5 mg 77347 Isoquercitrin* 25 mg 00140585 Menthofuran* 50 mg 04580595 Isorhamnetin 10 mg 38907 (+)-Menthofuran* 50 mg 04580595 Isorhamnetin* 10 mg 04290585 (+)-Menthofuran 1 mL, 5 mL 63661 Isorhamnetin-3-O-β-D glucopyranosyl- 10 mg 00960590 (−)-Menthol* 100 mg 00580590 (1š2)-β-D glucopyranosyl-(1š6)-β-D (−)-Menthol 1g 63660 glucopyranoside* (−)-Menthone 5 mL 63677 Isosilybin A 5 mg 97326 (−)-Menthone* 100 mg 04660585 Isosilybin B 5 mg 95684 Menthylacetat* 100 mg 04590595 Isosteviol 10 mg 92273 (1R)-(−)-Menthyl acetate 1 mL, 5 mL 45985 Isovitexin* 10 mg 01120590 trans-p-Methoxycinnamaldehyde 50 mg 61384 Isovitexin 5 mg 67135 Methyl trans-cinnamate 50 mg 75032 Isoxanthohumol 5 mg 55423 2-Methyl-3-buten-2-ol 1 mL 05392 Jasmon 1 mL 59975 3-O-Methylellagic acid 10 mg 93026 Kaempferide 10 mg 69545 Methyl eugenol 50 mg 04607 Kaempferol* 10 mg 00550580 7-O-Methylwogonin 5 mg 41442 Kaempferol 10 mg 96353 R-(+)-Methysticin 5 mg 80488 Kaempferol 3-glucoside 5 mg 68437 Myrcene* 50 mg 04600585 Kaempferol-3-glucoside* 10 mg 04500585 Myrcene 100 mg 64643

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

For more information, visit sigma-aldrich.com/medicinalplants 37

sh9885_Update Phytopharma Standards Brochure_v1.indd 37 07/07/16 2:29 pm Description Package Cat. No. Description Package Cat. No. Myricetin* 10 mg 05390590 Pinoresinol 10 mg 06709 Myricetin 10 mg 72576 Piperine 50 mg 75047 Myricitrin* 10 mg 02180585 Piperyline 10 mg 55805 Myricitrin 10 mg 67268 Poncirin 10 mg 77536 Myristicin 10 mg, 50 mg 09237 6-Prenylnaringenin 5 mg 75602 (±)-Naringenin 50 mg 52186 8-Prenylnaringenin 5 mg 75119 Naringenin 4',7-dimethylether 5 mg 76716 Primulaverin 5 mg 30147 Naringin 500 mg 91842 Primverin 5 mg 90657 Negundoside 10 mg 80724 Procyanidin A2 10 mg 28660 Neoandrographolide 5 mg 49879 Procyanidin B1 1 mg 19542 Neochlorogenic acid 5 mg 91213 Procyanidin B2 1 mg 42157 Neohesperidin 10 mg 40927 Procyanidin C1 5 mg 50878 Neohesperidin dihydrochalcone 100 mg 75041 Progoitrin potassium salt 10 mg 76197 trans-Nerolidol* 50 mg 04610590 Protocatechuic acid* 50 mg 03930590 trans-Nerolidol 100 mg 18143 Protocatechuic acid 50 mg 08992 Neryl acetate 1 mL 46015 Protopanaxadiol 10 mg 62685 Nobiletin 10 mg 92600 Protopanaxatriol 10 mg 42476 Nomilin 10 mg 77518 Protopin 10 mg 07267 Notoginsenoside R1 10 mg 77089 Pseudoginsenoside F11 10 mg 67530 N-Vanillylnonamide 50 mg, 15971 Pseudohypericin 5 mg 51593 100 mg Psoralen 10 mg 73633 Obacunone 10 mg 74191 Puerarin 10 mg 96006 Octanal 1 mL, 5 mL 52466 (+)-Pulegone* 100 mg 04620590 3-Octanone 5 mL 46214 (+)-Pulegone 5 mL 82569 Oenin chloride 10 mg 04288 Punicalagin 10 mg 50793 Oenothein B 10 mg 03805 Punicalin, mixture of anomers 10 mg 67988 Oleandrin 5 mg 06069 Pyrogallol 50 mg 06931 Oleanolic acid* 10 mg 03920590 Quercetin dihydrate* 50 mg 00200595 Oleanolic acid 10 mg 42515 Quercetin 3-glucoside 10 mg 16654 Oleuropein* 10 mg 05400590 Quercetin 3-glucuronide* 25 mg 00310590 Oleuropein 10 mg 92167 Quercetin 3-O-glucuronid 5 mg 90733 Orientin* 10 mg 03810585 Quercetin 3-O-rutinoside-7-O-glucoside 10 mg 55836 Orientin 5 mg 55736 Quercitrin* 25 mg 00740580 Osthole* 10 mg 02150595 trans-Quercus lactone 100 mg 72777 Oxybenzone 50 mg 59647 Quinine** 50 mg 69311 Oxypeucedanin 5 mg 42904 Rebaudioside A 10 mg 38462 Paeoniflorin 10 mg 75603 Rebaudioside B 10 mg 49747 Panax ginseng extract 150 mg 05115001 Rebaudioside C 10 mg 30987 Papaverine hydrochloride 500 mg PHR1182 Rebaudioside D 10 mg 19189 Passiflora incarnata extract 150 mg 05085001 Reserpine** 50 mg 06859 5-Pentadecylresorcinol 10 mg 91822 Resorcinol** 100 mg 53363 Peonidin 3-O-glucoside chloride 1 mg 42008 trans-Resveratrol** 100 mg 76511 Petunidin 3-O-β-D-glucoside chloride 10 mg 30638 Rhapontin 50 mg 94168 Phloretin 10 mg 91897 Rhein 10 mg 30873 Phloridzin dihydrate 50 mg 79589 Rosmarinic acid* 25 mg 00390580 p-Hydroxybenzoic acid 1g PHR1048 Rubiadin 10 mg 74553 Phyllanthin 10 mg 75110 Rubusoside 10 mg 62933 Physcion 10 mg 93893 Rutin trihydrate* 50 mg 00300590 Picein 10 mg 74192 Sabinen hydrate* 50 mg 04630590 Pikrosalvin (Carnosol) 10 mg 49702 Sabinene hydrate 500 mg 96573 (−)-β-Pinene* 100 mg 00080590 Safrole** 100 mg 08010 α-Pinene* 100 mg 00040590 Sakuranetin 10 mg 73422 (−)-α-Pinene 1 mL, 5 mL 80599 D-(−)-Salicin 100 mg 79588 (+)-β-Pinene 1 mL, 5 mL 80607 Salicylic acid** 50 mg 52341

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

38 Phytochemical Standards

sh9885_Update Phytopharma Standards Brochure_v1.indd 38 07/07/16 2:29 pm Description Package Cat. No. Description Package Cat. No. Salidroside* 10 mg 05410590 L-(+)-Tartaric acid** 100 mg 41447 Salidroside 25 mg 43866 Taxifolin* 10 mg 03890585 Salvianolic acid A 10 mg 97599 Taxifolin 25 mg, 100 mg 78666 Salvianolic acid B 10 mg 49724 Tectoridin 50 mg 89948 (−)-α-Santonin 10 mg 53653 Tectorigenin 25 mg 67359 Schaftoside 5 mg 42925 Terpinen 4-ol* 50 mg 03900590 Terpinen-4-ol 50 mg 49598 Schizandrin A 50 mg 90139 α-Terpinene 100 mg 72777 Sclareol 100 mg 49944 γ-Terpinene 1 mL, 5 mL 86476 Scopoletin 10 mg 38332 γ-Terpinene* 100 mg 04640590 Scutellarin 10 mg 73577 α-Terpineol* 100 mg 03420590 Senecionine, dried down solution 0.05 mg 37031 (+)-α-Terpineol 5 mL 83073 Senecionine 5 mg 50351 (−)-Δ9-Tetrahydrocannabinol, solution ~1 1 mL 56296 Seneciphylline, dried down solution 0.05 mg 37033 mg/ mL in ethanol Seneciphylline 5 mg 73913 Tetrahydrocurcumin 10 mg 50202 Senkirkine, dried down solution 0.05 mg 37032 Theaflavin 1 mg 55016 Senna extract 150 mg 05475001 Theaflavin 3,3'-digallate 1 mg 92223 Sennoside A* 25 mg 01870575 Theaflavin monogallate 1 mg 53963 Sennoside A 5 mg, 25 mg 68909 Theophylline 1g PHR1023 Sennoside B* 25 mg 00530580 Thujone Standard Mixture 1 mL, 5 mL 04314 Thymol* 100 mg 00670590 Sennoside B 25 mg 75412 Thymol 500 mg 72477 Sennosid C 10 mg 73235 Tiliroside 10 mg 79257 Sennoside D 10 mg 16383 Tribulosin 10 mg 51675 Serratol 5 mg 78689 Trigonelline hydrochloride 100 mg 61407 Sesamin 10 mg 59867 1,3,6-Tri-O-galloyl-β-D-glucose 10 mg 78864 Shatavarin IV 10 mg 30151 (S)-ar-Turmerone 10 mg 42258 Shikimic acid 50 mg 69686 Umbelliferone 50 mg 54826 [6]-Shogaol 10 mg 39303 Umckalin 10 mg 50792 Silybin* 25 mg 02000585 Ursolic acid* 10 mg 03240595 Silybin B 5 mg 59527 Ursolic acid 5 mg, 25 mg 89797 Silybum marianum extract 150 mg 05135001 (+)-Valencene 50 mg 06808 Silychristin 10 mg 51681 Valerenic acid* 10 mg 02010595 Silydianin 10 mg 30494 Valeriana officinalis extract 150 mg 05105001 trans-Sinapic acid 50 mg 93878 Vanillic acid** 50 mg 68654 Sinensetin 10 mg 89392 Vanillic acid 4-β-D-glucoside 5 mg 14515 Vanillin** 50 mg 30304 (−)-Sinigrin hydrate 10 mg 00290 N-Vanillylnonanamide 50 mg, 100 mg 15971 β-Sitosterol* 10 mg 05410590 Vasicine 10 mg 92951 β-Sitosterol 10 mg 43623 Verbascoside* 10 mg 00820580 β-Sitosterol β-D-glucoside 10 mg 89851 (1S)-(−)-Verbenone 1 mL, 5 mL 94882 Sodium 3-(3,4-dihydroxyphenyl)-DL-lactate 5 mg, 25 mg 39363 Vescalagin 5 mg 76418 Sodium propionate** 100 mg 49894 Vicine 10 mg 78260 Spiraeoside 5 mg 91802 Vincamine 50 mg 75778 Steviol 10 mg 19345 Vitexin* 10 mg 00840595 Steviolbioside 10 mg 59754 Vitexin 10 mg 49513 Stevioside* 25 mg 05420590 Vitexin 2-O-rhamnoside* 10 mg 00660585 Stevioside 10 mg 50956 Vitexin 4''-O-glucoside 5 mg 43907 Succinic acid** 100 mg 49893 10 mg 56639 Swertiamarine 10 mg 90957 Withaferin A 10 mg 89910 Synephrine 50 mg 75256 Withanolide A 10 mg 74776 Syringic acid 100 mg 63627 Withanolide B 10 mg 94284 Withanone 10 mg 90896 Syringin (Eleutherosid B) 10 mg 90974 Withanoside IV 10 mg 94186 Tangeretin 10 mg 91004 Withanoside V 10 mg 66042 Tanshinone I 10 mg 80714 Xanthohumol* 10 mg 01130595 Tanshinone II A 10 mg 51704 Xanthotoxin 50 mg 56448 3β-Taraxerol 10 mg 75934 Yangonin 5 mg 75575

*Primary pharmaceutical reference standard HWI **TraceCERT®, certified reference material

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Pharmacopeia Compendial Standards Mycotoxins For testings according to pharmacopoeia monographs, Sigma- Fungal infection of plants can lead to mycotoxin contamination Aldrich distributes compendial standards from the USP and the of plant derived products. To ensure the safety of these products, European Pharmacopoeia (EP). Find the corresponding product testing for mycotoxins is therefore important. Find a comprehensive listings at sigma-aldrich.com/usp and sigma-aldrich.com/ep product list as well as the mycotoxin standards brochure on sigma- respectively. aldrich.com/mycotoxins. Inorganic Certified Reference Materials (CRMs) Microbiological CRMs (Vitroids™) Herbal Medicinal Products should be tested for the presence of • Defined CFU & low standard deviation (ISO 17025) potentially harmful inorganics such as Cadmium, Lead or Mercury. • Economic, convenient and easy to use Under the TraceCERT brand, Sigma-Aldrich offers a comprehensive range of inorganic CRM solutions, suitable for ICP, AAS and Ion • Long shelf life Chromatography. The products are manufactured according to Vitroids™ contain viable microorganisms in a certified quantity (ISO ISO/IEC 17025 and ISO Guide 34 accreditation. An overview and 17025), produced under reproducible conditions (ISO Guide 34) comprehensive information as well as a brochure download link can with strains obtained from ATCC and NCTC. Consisting of bacteria or be found on sigma-aldrich.com/inorganiccrm. fungi in a solid water soluble matrix, they are stable for at least one year and are in a viable stage with a shelf life of 1-3 years. The disc to disc reproducibility goes down 4% at a level of 100 colony forming Pesticides units (CFU). Each batch poses a comprehensive certificate of analysis Especially in plant materials originating from cultivation, traces of reporting the CFU, an expanded uncertainty, more details about the pesticides might be present. For their analysis, Sigma-Aldrich offers one method and the number of passages. Visit our website at sigma- of the most comprehensive product range of pesticide Standards and aldrich.com/vitroids. CRMs, under the well known brands PESTANAL and TraceCERT. A complete list of the more than 1400 products are listed on Visit sigma-aldrich.com/standards for our complete sigma-aldrich.com/pesticides. offering of analytical standards and certified reference materials.

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sh9885_Update Phytopharma Standards Brochure_v1.indd 40 07/07/16 2:29 pm