Flavonoids and Terpenes • Analytical Standards for Terpenes and Flavonoid Analysis • Single-Element Standards and Mixes Available
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Retention Indices for Frequently Reported Compounds of Plant Essential Oils
Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5. -
Borneol - Camphor - Isoborneol
EXP. 35 A & B OXIDATION-REDUCTION SCHEME: BORNEOL - CAMPHOR - ISOBORNEOL LEARNING OBJECTIVES: To illustrate the concepts of oxidation and reduction in organic chemistry, to illustrate the stereochemical effects of these reactions in certain systems, to use IR spectroscopy to characterize diastereomers and monitor reactions. QUIZ PREPARATION: Recitation notes and readings assigned in the syllabus. OXIDATION AND REDUCTION IN ORGANIC CHEMISTRY The concepts of oxidation and reduction in chemistry are fundamentally related to the loss and gain of electrons, respectively. For a specific atom, oxidation brings about an increase in the oxidation number, whereas reduction does the opposite. This is of course true in organic reactions as well, but it is frequently less clear where the gain or loss of electrons is taking place. For this reason, the concepts of oxidation and reduction are addressed from a different perspective in organic chemistry. Since carbon is the most important element in organic chemistry, we can define oxidation as a process whereby carbon gains bonds to more electronegative atoms. These can be any atoms more electronegative than carbon, such as chlorine or sulphur, but the most commonly seen in organic oxidations is oxygen. The more bonds to oxygen, the higher the oxidation state of the carbon involved. Examples of oxidation reactions are those that convert alkanes into alcohols, or alcohols into carbonyl compounds. The functional groups that contain the most highly oxidized form of carbon in organic compounds are the carboxylic acids and their derivatives. Reduction is the opposite of oxidation. We can define reduction as a process whereby carbon adds bonds to less electronegative atoms. -
Variation in the Composition of the Essential Oil of Valeriana Officinalis L
Proc. Estonian Acad. Sci. Chem., 2007, 56, 2, 67–74 Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia Ain Raala, Anne Oravb*, Elmar Araka, Tiiu Kailasb, and Mati Müüriseppb a Institute of Pharmacy, University of Tartu, Nooruse 1, 50411 Tartu, Estonia b Institute of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia Received 31 January 2007, in revised form 12 March 2007 Abstract. The volatile constituents from roots of Valeriana officinalis L. were investigated using GC and GC/MS methods. Valerianae radix samples were obtained from retail pharmacies or cultivated in Estonia. The roots of five V. officinalis samples yielded 0.28–1.16% essential oil in the cut drug, which usually corresponded (four samples) to the European Pharmacopeia standard (0.3%). The basic oil components among the identified 84 compounds were isovaleric acid (0–2.1%), α-pinene (0.4–3.6%), α-fenchene (0.6–5.8%), camphene (0.6–5.9%), bornyl acetate (8.8–33.7%), myrtenyl acetate (2.0–7.2%), alloaromadendrene (0.3–7.6%), myrtenyl isovalerate (1.1–2.5%), spathulenol (0.7–4.1%), sesquiterpene alcohol (0.8–6.6%), valerianol (0.3–16.7%), valeranone (0.5–9.4%), and valerenal (tr–14.7%). Valerian root oil from Estonia (four samples) was rich in bornyl acetate and valerenal. Bornyl acetate, valerianol, and valeranone dominated in one Estonian sample. Key words: Valeriana officinalis L., essential oil, bornyl acetate, valerenal, valerianol, valeranone. INTRODUCTION Valerian (Valeriana officinalis L.) is a well-known and frequently used medicinal plant, which has a long proven history of efficacy. -
An Artifact in a Synthetic Pine Oil
RESEARCH NOTE J. Ess. Oil Res., 3, 41-42 (Jan/Feb 1991) An Artifact in a Synthetic Pine Oil Duane F. Zinkel USDA Forest Service, Forest Products Laboratory* One Gifford Pinchot Drive Madison, WI 53705-2398 ABSTRACT: The isopropyl ether of a-terpineol was identified as an artifact in the synthetic pine oil produced when isopropyl alcohol was used as the emulsifier. KEY WORD INDEX: Synthetic pine oil, a-terpineol isopropyl ether, terpinen-4-ol isopropyl ether, turpentine. INTRODUCTION: The manufacture of synthetic pine oil is the primary use for turpentine. The synthesis involves the acid-catalyzed hydration of a-pinene at the in terface ofan emulsion of pinene/mineral acid (1). Various emulsifiers have been used, one of which is isopropyl alcohol. Our gas chromatographic examination of a commercial distilled pine oil, produced using the isopropyl alcohol emulsifier, revealed the presence of 4-5% of a higher boiling component product not present originally in the turpentine. EXPERIMENTAL: NMR spectra were obtained at 310 K with a Bruker WM250 (250 MHz proton and 62.9 MHz carbon) FT spectrometer controlled by an Aspect 2000A minicomputer; DEPT spectra were obtained with a standard Bruker program. Gas chromatography was done with a Hewlett Packard 5880 gas chromatograph (FID) and fused-silica columns: a DB-1 (a methyl silicone) column from J & W Scientific (Folsom, CA), 15m x 0.25mmi.d. witha 0.1-µmfilmoperatedat60°Cand a Carbowaxcolumn,30m x 0.25mm with a 0.25-µm film temperature programmed from 60°C to 225°C at 8°C/min. isopropyl etherwas isolated by liquid chromatography. -
(19) United States (12) Patent Application Publication (10) Pub
US 20060081822A1 (19) United States (12) Patent Application Publication (10) Pub. N0.: US 2006/0081822 A1 Koetzle (43) Pub. Date: Apr. 20, 2006 (54) METHOD TO INCREASE FLASH POINTS OF (52) US. Cl. ............................................................ .. 252/601 FLAMMABLE SOLVENTS (76) Inventor: A. Richard Koetzle, Rochester, NY (57) ABSTRACT (Us) Correspondence AddreSSI The present invention relates to a method to decrease the A- RICHARD KOETZLE ?ammability of normally ?ammable alcohols and solvents. 134 STONECLIFF DRIVE The additive is Alpha Terpineol, Which Will increase the ROCHESTER’ NY 14616 (Us) ?ash point of ?ammable alcohols or solvents, by blending the Terpineol into the ?ammable solvent or alcohol. Solvents (21) Appl' NO" 10/968’441 such as acetone, methanol, ethylacetate, ethanol and Xylene, (22) Filed, Oct 20 2004 to name a feW, increases ?ash points by 50° C. to 60° C., by i ’ addition of 12-14% terpineol. The said solvent can then be Publication Classi?cation blended With other organic solvents to produce performance solvents, such as paint strippers With ?ash points greater (51) Int. Cl. than 1400 F. and meet Federal and state Volatile Organic C 09K 21/00 (2006.01) Compound regulations. US 2006/0081822 A1 Apr. 20, 2006 METHOD TO INCREASE FLASH POINTS OF [0008] The organic solvent or combination of solvents can FLAMMABLE SOLVENTS comprise up to 99 Weight percent of the composition in total, and may be the combination of tWo or more different types BACKGROUND OF THE INVENTION of organic solvents. A typical combination may comprise; [0001] Many industrial processing cleaning compositions [0009] 1.0 to 99 Weight percent organic solvent. -
A New Source of Natural D-Borneol and Its Characteristic
Journal of Medicinal Plants Research Vol. 5(15), pp. 3440-3447, 4 August, 2011 Available online at http://www.academicjournals.org/JMPR ISSN 1996-0875 ©2011 Academic Journals Full Length Research Paper A new source of natural D-borneol and its characteristic Lei Chen 1, Jianyu Su 1*, Lin Li 1, Bing Li 1 and Wang Li 2 1Department of Food Science and Technology, South China University of Technology, 510642 Guangzhou, Peoples Republic of China. 2Food Safety Key Laboratory of Guangdong Province, College of Food Science, South China Agricultural University, 510642 Guangzhou, Peoples Republic of China. Accepted 28 February, 2011 The essential oils from leaves of Mei Pian tree (a Cinnamomun burmannii physiological type), were obtained by hydro-distillation and analyzed by gas chromatography and mass spectrometry (GC/MS). Forty compounds representing 99.61% of the total oil containing D-borneol (78.6%) as the major component were obtained. D-borneol was purified by sublimation, and the characteristic of the refined D-borneol was compared with standard D-borneol and synthetic borneol by infrared spectra analysis and optical activity analysis. The chemical composition and the optical rotation of refined D-borneol from leaves of Mei Pian tree were extremely similar to the standard D-borneol and materially surpass synthetic borneol. Antioxidant activities of the refined D-borneol and standard D-borneol were determined by testing their DPPH and hydroxyl radicals scavenging activities and the reducing power. The refined D-borneol and standard D-borneol had the same antioxidant activity. They exhibited higher hydroxyl radicals scavenging activity, but weaker reducing power, compared with the synthetic borneol. -
Valencene Synthase Polypeptides, Encoding Nucleic Acid Molecules and Uses Thereof
(19) TZZ¥Z_T (11) EP 3 085 778 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 26.10.2016 Bulletin 2016/43 C12N 9/88 (2006.01) C12P 5/00 (2006.01) C12N 15/60 (2006.01) C12N 5/10 (2006.01) (2006.01) (2006.01) (21) Application number: 16171175.9 C12N 15/82 C12P 7/26 (22) Date of filing: 11.03.2014 (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • SARAN, Dayal GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Lexington, KY (US) PL PT RO RS SE SI SK SM TR • PARK, Grace Eunyoung Lexington, KY (US) (30) Priority: 14.03.2013 US 201361852462 P (74) Representative: Rees, Kerry (62) Document number(s) of the earlier application(s) in WP Thompson accordance with Art. 76 EPC: 138 Fetter Lane 14718824.7 / 2 970 934 London EC4A 1BT (GB) (71) Applicant: Evolva, Inc. Wilmington, New Castle County, DE 19808 (US) (54) VALENCENE SYNTHASE POLYPEPTIDES, ENCODING NUCLEIC ACID MOLECULES AND USES THEREOF (57) The present invention is directed to a recom- thase polypeptide, or a catalytically active fragment binant cell that produces valencene and aristolochene, thereof. The presnt invention also provides methods of wherein the recombinant cell comprises a heterologous producing valencene and aristolochene using a recom- nucleic acid that encodes a valencene synthase polypep- binant cell of the invention and compositions comprising tide, or a catalytically active fragment thereof; or the re- valencene and aristolochene. -
Natural Borneol Recycling from Cinnamomum Camphor Chvar
Chen et al Tropical Journal of Pharmaceutical Research September 2014; 13 (9): 1463-1470 ISSN: 1596-5996 (print); 1596-9827 (electronic) © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved . Available online at http://www.tjpr.org http://dx.doi.org/10.4314/tjpr.v13i9.12 Original Research Article Natural Borneol Recycling from Cinnamomum camphor chvar. Borneol Oil Residue by Fractional Distillation and Recrystallization Xiao Ying Chen 1, Xiao Ning Zhao 2, Hui Fang Zeng 2, Jian Hui Xie 1,3 , Xiao Lu Chen 2, Yong Zhuo Liang 1, Qi Duan Wu 2, Zi Ren Su 1,5 , Hong Feng Wang 4* and Xiao Ping Lai 1,5 * 1School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510006, 2The First Affiliated Hospital of Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510405, 3The Second Affiliated Hospital of Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510405, 4Biotechnology Division, Guangdong Academy of Forestry, Guangzhou, 5Dongguan Mathematical Engineering Academy of Chinese Medicine, Guangzhou University of Chinese Medicine, Dongguan, 523808, China *For correspondence: Email: [email protected], [email protected]; Tel: +86-20-39358517; Fax: +86-20-39358390 Received: 10 May 2014 Revised accepted: 7 August 2014 Abstract Purpose: To establish an efficient method to recycle natural borneol from Cinnamomum camphor chvar. Borneol oil residue. Methods: The fractions and raffinate of the oil residue of Cinnamomum camphor chvar. Borneol were obtained by fractional distillation, and analyzed by gas chromatography with flame ionization detector (GC-FID) and gas chromatography- mass spectrometry (GC-MS). Natural borneol was purified by recrystallization and suction filtration. -
Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol. Qiang Tan Louisiana State University and Agricultural & Mechanical College
Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1996 Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol. Qiang Tan Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Tan, Qiang, "Immobilization of P. Digitatum and Bioconversion of Limonene to Alpha-Terpineol." (1996). LSU Historical Dissertations and Theses. 6312. https://digitalcommons.lsu.edu/gradschool_disstheses/6312 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand comer and continuing from left to right in equal sections with small overlaps. -
Essential Oil Components of Alaska Cedar Heartwood Signature Redacted for Privacy
AN ABSTRACT OF THE THESIS OF Yeping Xiong for the degree of Master of Science in Forest Products presented on December 8, 2000. Title: Essential Oil Components of Alaska Cedar Heartwood Signature redacted for privacy. Abstract approved: 0 JosephVKarchesy C/7 The essential oil of Alaska cedar heartwood is known to contain compounds which contribute to the remarkable durability of this species. While previous research has identified several compounds, a complete description of this oil, which has a "burnt-grape fruit" odor, has not been undertaken. In this research a profile of the oil is given in which the major components are identified by GC-MS, isolation and spectroscopic techniques. The major components of the steam distilled essential oil were identified as nootkatin, nootkatone, valencene, nootaktene, carvacrol, methyl carvacrol, nootkatol, and eremophil- 1(10),11-dien-13-ol. In addition, it was found that the diethyl ether extract of the heartwood contained 1(10)- eremophilen-11,12-epoxide as a major component in addition to the compounds found in the steam distilled essential oil. 1(10)-Eremophilen-11,12-epoxide apparently does not survive the condition of steam distillation. Nootkatol, eremophil-1(10),11-dien-13-ol and 1(10)- eremophilen-11,12-epoxide have not been previously reported in Alaska cedar. Nootkatol is a known compound having been reported in other plants. However, eremophil-1(10),11-dien-13-ol and 1(10)-eremophilen- 11,12-epoxide represent new chemical structures to science being described here for the first time. Essential Oil Components of Alaska Cedar Heartwood by Yeping Xiong A THESIS submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science Presented December 8, 2000 Commencement June, 2001 Master of Science thesis of Yeping Xiong presented on December 8, 2000 APPROVED: Signature redacted for privacy. -
Odor Impact of Volatiles Emitted from Marijuana, Cocaine, Heroin and Their Surrogate Scents Somchai Rice Iowa State University, [email protected]
Agricultural and Biosystems Engineering Agricultural and Biosystems Engineering Publications 12-2015 Odor impact of volatiles emitted from marijuana, cocaine, heroin and their surrogate scents Somchai Rice Iowa State University, [email protected] Jacek A. Koziel Iowa State University, [email protected] Follow this and additional works at: http://lib.dr.iastate.edu/abe_eng_pubs Part of the Agriculture Commons, Bioresource and Agricultural Engineering Commons, and the Toxicology Commons The ompc lete bibliographic information for this item can be found at http://lib.dr.iastate.edu/ abe_eng_pubs/707. For information on how to cite this item, please visit http://lib.dr.iastate.edu/ howtocite.html. This Article is brought to you for free and open access by the Agricultural and Biosystems Engineering at Iowa State University Digital Repository. It has been accepted for inclusion in Agricultural and Biosystems Engineering Publications by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Odor impact of volatiles emitted from marijuana, cocaine, heroin and their surrogate scents Abstract Volatile compounds emitted into headspace from illicit street drugs have been identified, but until now odor impact of these compounds have not been reported. Data in support of identification of these compounds and their odor impact to human nose are presented. In addition, data is reported on odor detection thresholds for canines highlighting differences with human ODTs and needs to address gaps in knowledge. New data presented here include: (1) compound identification, (2) gas chromatography (GC) column retention times, (3) mass spectral data, (4) odor descriptors from 2 databases, (5) human odor detection thresholds from 2 databases, (6) calculated odor activity values, and (7) subsequent ranking of compounds by concentration and ranking of compounds by odor impact (reported as calculated odor activity values). -
Kinetics and Mechanism of Oxidation of Borneol (Cyclic Secondary Alcohol) by Trichloroisocyanuric Acid in Acidic Medium
Jr. of Industrial Pollution Control 25 (1) (2009) pp 1-8 © Enviromedia Printed in India. All rights reserved KINETICS AND MECHANISM OF OXIDATION OF BORNEOL (CYCLIC SECONDARY ALCOHOL) BY TRICHLOROISOCYANURIC ACID IN ACIDIC MEDIUM NAVNEET SHARMA* AND MAMTA GOEL** * Department of Chemistry, H.R. Institute of Technology, Ghaziabad, U.P., India **Department of Chemistry, SGIT, Ghaziabad, U.P., India Key words : Kinetics, Oxidation, Borneol, Trichloroisocyanuric acid, Perchloric acid. ABSTRACT The kinetics of Oxidation of borneol (C10H18O) [endo-1, 7, 7-Trimethyl bicyclo (2, 2, 1) heptan-2-ol] by aqueous perchloric system, yields of ketone in the presence of Trichloroisocyanuric acid at 300C. The stoichiometry is (1:1) and the main oxidation product is Camphor which is studied by TLC using benzene as a solvent and by spraying with 2, 4-dinitrophenyl hydrazine reagent. The observed rate of oxidation shows a first order dependence on both borneol and TCICA (Oxidant). INTRODUCTION have been studied by various oxidants such as N- Bromo-acetamide8, N-Bromoseccharin9, N-Chloro R- Oxidation of organic compounds is one of the most 2, C-6 Diphenyl-t-3 Methyl piperedin-4-on (NCP)10, important reaction in organic synthesis. For this pur- Cerium (IV) Catalysed by chromium (III)11,Cromium pose, some new oxidizing reagents have been pre- (VI) in presence of oxalic acid12, by aqueous chlorine13 pared1-3. In the recent years, studies of oxidation of and oxidation of organic alcohol by pyrazinium various organic compounds in presence of perchlo- dichromate14. The Oxidation of Borneol has been stud- ric acid by halo-compounds4. Borneol is a white crys- ied by chlorine15 and copper (II)-ß-cyclodextrin in py- talline bicyclic terpene alcohol and a component of ridine acetic acid-hydrogen peroxide system16, but many essential oils 5 and it is natural insect repel- there is no references in the literature on the oxida- lent.6 Borneol is easily oxidized to ketone and occurs tion of borneol by TCICA.