Cannabis Testing Standards

As the industry grows, various stakeholders are working towards standardization within the industry. Cayman provides analytical reference standards and ISO 17034-produced Certified Reference Materials to identify and quantitatively measure the components found in Cannabis products to aid in potency testing, terpene profiling, and analysis of contaminants. Along with single-component standards, we specialize in the production of pre-made, multi-component mixtures that are designed to improve quantitation accuracy and streamline workflows.

PHYTOCANNABINOIDS

TERPENES IMPROVE ACCURACY & REDUCE CONSUMABLE RESIDUAL SOLVENTS COST, VARIABILITY, AND TIME!

PESTICIDES & MYCOTOXINS

www.caymanchem.com · (800) 364-9897 Request a PHYTOCANNABINOID POSTER for your lab!

PHYTOCANNABINOID GUIDE NAMING BIOSYNTHESIS, NAMING, AND NUMBERING NUMBERING CONVENTIONS CONVENTIONS When naming phytocannabinoids, the prefix “cannabi” always appears in the main scaffold which CLASSIC OLIVETOL SERIES The two most common conventions for numbering THC are the dibenzopyran and 1 drives the name and acronym of each compound. The resorcinol root will designate the original C5 monoterpene systems.2,3 The biphenyl and Lord Alexander Todd numbering series and its C3 and C1 homologs. Listed here are the main scaffolds observed in phytocannabinoids. Olivetolic phytocannabinoids are considered classic, as these are systems are older and less common.2,3 A simple terpenoid numbering system is Because of the prevalence of the olivetolic root, the standard names will all contain the suffix -OL or used for CBC, CBG, CBE, and CBL structures.3,4 –NOL, with a few exceptions. When describing the C3 and C1 homologs, the scaffold name is amended the compounds that are ubiquitous to all varietals of marijuana. This by dropping the -OL and replacing the suffix with -VARIN/VARINOL (C3) or -ORCIN/ORCINOL (C1). series is not only the most dominant in the Cannabis species but The orcinolic series is unique in that the suffix has also been placed within the scaffold name Most Common Systems (-ORC- as in → cannabiorcochromene). OH also the most widely studied in the literature. OH Dibenzopyran Numbering Monoterpene Numbering

11 7

9 Resorcinol Root Name O HO 6 8 10 1 Δ8- (Δ8-THC) OH 6 2 5 7 OH OH OH (CBD) H 1 5 3 8 (ISO60158 | 14042) 6a 2' (ISO60156 | 90080) 7 4 4 2' 10a 2 1' 3 3' 1' H 3' OH O 8 2 3 HO HO HO H OH 6 6' H O 4' 6' Olivetol Divarin Orcinol OH 5 4 10 9 1 4' 7 5' 5' -OL -VARIN, -VARINOL -ORCIN, -ORCINOL, -ORC- OH 11 11 7 H O 9 9 O 9 9 8 8 10 OH Δ -Tetrahydrocannabinolic Acid A (THCA-A) (Δ -THCA-A) 10 OH 2 6 OH O OH OH Main Scaffold Motifs and Names (ISO60175) H H 5 3 (CBL) 1 1 2' 5 3 HO 7 6a 7 6a 4 4 2' (22036 | 9002438) 10a 2 10a 2 1' 1' (CBG) (E isomer) OH 3' 3' Monocyclic Bicyclic Tricyclic Tetracyclic H H OH (20164 | 15293) 8 8 O 3 3 6' 6 O 6 O 4' 6' OH 9 9 Cannabinerol (CBNR) (Z isomer) HO 9 4' OH HO 5 4 5 4 10 10 9 OH Δ -Tetrahydrocannabinol (THC) (Δ -THC) 5' 5' OH O (CBND) (ISO60157 | 12068) Cannabidiolic Acid (CBDA) Δ8 Δ9 Δ6 Δ1(2) O (18090) (9002479) Monoterpene numbering designates the dibenzopyran Δ8 HO R O R Dibenzopyran numbering designates the double bond of O R 6 9 1 2 OR HO R 8 9 configuration as Δ . The dibenzopyran Δ configuration is Δ (or Δ ). CannaBiGerol O OH interest as Δ or Δ . CannaBiChromene CBG iso-TetraHydroCannabinol CannaBicycLol 9 9 CBC Δ -Tetrahydrocannabinolic Acid B (Δ -THCA-B) CBN iso-THC CBL HO HO HO Older/Less Common SystemsTerpenoid System HO OH OH OH OH OH OH O OH OH O Biphenyl Numbering Terpenoid Numbering

OH 10' 9' O R 1' 1 OH R OR OR O 10' 6 HO 2' 2 1 O HO 3 7' 5' 1' 4 2 6 CannaBiciTran 3' 2 TetraHydroCannabinol CannaBiTriol 7' 5' CannaBiDiol Cannabitriol (CBT) (triol) Cannabiripsol (CBR) (CBE) 5 1 3' 5 3 8' 6' 4' 2' ‘Citran’ CBT 2' THC ‘Triol’ CBT 6 O CBD (21092) 1' 8' 4' 4 5 3 3' 6' 9' HO HO CBDA 4 THCA O Cannabichromene 6' 4' Cannabigerol synthase (CBC) OH O O synthase OH 5' (CBG) Todd Numbering 7 HO HO

R 1 O R R H HO HO Cannabifuran (CBF) O 6 2 1' OH HO 2' H 7' 5 3 6' 1 CannaBiNoDiol CannaBiElsoin CannaBiFuran Cannabichromene (CBC) 5' 4 2' 6 6' 3' 5' 1' 2 CBND CBE CBF (ISO60163 | 26252) 4' 6' 6" 4' H OH O 3' 1' 8 5 OH 2' 1" 5' 4' 3' 3 5" HO 4 O OH 5 HO OH 3 10 9 4 OH 2 1 4" Cannabicyclol 2" Cannabielsoin O O (CBE) (CBL) O OH 3" Cannabinolic Acid (CBNA) OR Cannabinol (CBN) OH O OH O (ISO60183 | 25495) anna i ipsol C B R OH OH 2. Mechoulam, R. and Gaoni, Y. Fortschr. Chem. Org. Naturst. 25, 175-213 (1967). CBR O 3. ElSohly, M.A. and Slade, D. Life Sci. 78(5), 539-548 (2005). CBCA O HO exo-Tetrahydrocannabinol (exo-THC) HO 4. Hanuš, L.O., Meyer, S.M., Muñoz, E., et al. Nat. Prod. Rep. 33(12), 1357-1392 (2016). “M” is indicative of methyl ester when added to the end of the acronym (CBGA) (E isomer) synthase (CBCA) OH (20019 | 9001572) (30879 | 9001573) (e.g., CBDM = cannabidiol methyl ester). “A” is indicative of the carboxylated O Cannabinerolic Acid (CBNRA) (Z isomer) O and is added to the very end of the acronym (e.g., THCA = tetrahydrocannabinolic acid). HO HO O 1. Brenneisen, R. Chemistry and analysis of phytocannabinoids and other Cannabis Cannabielsorcinol (CBEO) Cannabinodiorcin (CBNDO) Cannabicitran (CBT) (citran) constituents. Marijuana and the . ElSohly, M.A., editor, Humana Press (2007). OH (21295) O OH O

OH HO HO Cannabinodivarin (CBNDV) OH Cannabifuraorcin (CBFO) Cannabidiorcin (CBDO) Heat, Light, and Biosynthesis Cannabifuravarin (CBFV) Also known as O-1821 (10006804) Oxidation Exposure Geranyl- Enzymes transferase OH OH O O OH

OH OH HO (CBDV) HO (20165 | 9001574) OH Cannabidiorcinic Acid (CBDOA) Cannabidivarinic Acid (CBDVA) (30245 | 9001575) OHO OH ORCINOL SERIES HO VARINOL SERIES Orcinolic phytocannabinoids have been identified Olivetolic Acid Varinolic cannabinoids were once rare but are now H OH (26282) OH H H O O H in Nepalese and Brazilian samples but are also found OH targets of selective breeding. They have also been H H as major compounds in non-Cannabis species O O O O O exhibited in higher abundance in C. indica over C. sativa. such as Rhododendron. Cannabicyclorcinol (CBLO) Cannabicitraorcin (CBTO) (citran) Cannabicitravarin (CBTV) (citran) Cannabicyclovarin (CBLV) O OH Cannabielsovarin (CBEV) CoA-S OH Hexanoyl-CoA OH OH OH OH O OH OH O OH HO OH OH HO Cannabigerorcin (CBGO) (E isomer) Cannabigerovarin (CBGV) (E isomer) OH O O OH (23257) O O O O (29117 | 9002437) 9 9 Δ9- (THCV) (Δ9-THCV) Δ -Tetrahydrocannabiorcin (THCO) (Δ -THCO) Cannabinerorcin (CBNRO) (Z isomer) Cannabinerovarin (CBNRV) (Z isomer) Cannabichromeorcinic Acid (CBCOA) Cannabichromeorcin (CBCO) (CBCV) Cannabichromevarinic Acid (CBCVA) (18091) (21742) (21974) O O exo-Tetrahydrocannabiorcin (exo-THCO) exo-Tetrahydrocannabivarin (exo-THCV)

HO HO Polyketide OH OH OH OH synthase HOHO HO OH OH OH O O OH OH OH O O OH OHO O O O OH OH HO OH Geranyl- OH HO Geranyl- HO CoA-S S-CoA O O HO HO OH OH O O O transferase Ethanoyl-CoA Butanoyl-CoA transferase O Cannabiripsorcinol (CBRO) Cannabitriorcinol (CBTO) (triol) Cannabigerorcinic Acid (CBGOA) (E isomer) Varinolic Acid Cannabigerovarinic Acid (CBGVA) (E isomer) Cannabitrivarinol (CBTV) (triol) Cannabiripsovarinol (CBRV) Δ9-Tetrahydrocannabiorcinic Acid (Δ9-THCOA) Orcinolic Acid Tetrahydrocannabivarinic Acid (Δ9-THCVA) (23258) OO (26283) (29787 | 25469) Cannabinerorcinic Acid (CBNROA) (Z isomer) 3 x Cannabinerovarinic Acid (CBNRVA) (Z isomer) (21259) CoA-SOH

OH O OH OH OH O OH OH OH HO O O O O O O 8 8 Δ8-Tetrahydrocannabivarin (Δ8-THCV) Cannabinorcin (CBO) Cannabinorcinic Acid (CBOA) Δ -Tetrahydrocannabiorcin (Δ -THCO) © 2018 Cayman Chemical Cannabivarinic Acid (CBVA) (CBV) Revised September 2020 (27322) (21664)

A guide to the biosynthesis, naming, and numbering of phytocannabinoids

Visit www.caymanchem.com/literature

www.caymanchem.com · (800) 364-9897 Phytocannabinoids Identify and quantitatively measure more than 25 unique phytocannabinoids in your samples using Cayman’s single-component Certified Reference Materials (CRMs). Multi-component mixtures are also available to streamline the quantitation of multiple phytocannabinoids.

Single- and Multi-Component CRMs · Sold as quantitative solutions in sealed ampules · Formulated as DEA exempt preparations · Manufactured and tested to meet ISO/IEC 17025 and ISO 17034 international standards · Includes a certified property and uncertainty value for metrological traceability

INCLUDED IN MULTI-COMPONENT PHYTOCANNABINOID MIXTURES

Phytocannabinoid Phytocannabinoid Phytocannabinoid Phytocannabinoid Mixture 5 (CRM) Mixture 6 (CRM) Mixture 10 (CRM) Mixture 11 (CRM) Item No. 25076 Item No. 25077 Item No. 21305 Item No. 21306 Item No. Single-Component CRMs 500 µg/ml each 500 µg/ml each 250 µg/ml each 250 µg/ml each

ISO60156 Cannabidiol (CRM)

ISO60157 Δ9-THC (CRM)

ISO60175 THCA-A (CRM)

ISO60183 Cannabinol (CRM)

18090 Cannabidiolic Acid (CRM)

20164 Cannabigerol (CRM)

ISO60163 (±)-Cannabichromene (CRM)

20165 Cannabidivarin (CRM)

20019 Cannabigerolic Acid (CRM)

ISO60158 Δ8-THC (CRM)

18091 Tetrahydrocannabivarin (CRM)

30879 (±)-Cannabichromenic Acid (CRM) View our range of pre-made CRM mixtures designed 21742 (±)-Cannabichromeorcin (CRM) to simplify workflows and provide super reproducibility, 21974 (±)-Cannabichromevarin (CRM) accuracy, and precision at 22036 (±)-Cannabicyclol (CRM) www.caymanchem.com/phytomixes 21295 Cannabicitran (CRM)

30245 Cannabidivarinic Acid (CRM)

29117 Cannabigerovarin (CRM) Learn how pre-made mixtures improve quantitation accuracy in our app note at 29787 Cannabigerovarinic Acid (CRM) www.caymanchem.com/CRMmixtures 21259 Tetrahydrocannabivarinic Acid (CRM) DEA exempt applies to US only. Products may be controlled in other countries. Please verify with your local distributor.

1180 East Ellsworth Road · Ann Arbor, MI · 48108 · USA Terpenes Conveniently build a terpene profile for different strains of Cannabis using a pre-made, multi-component solution containing commonly found terpenes or by using qualitative single-component standards.

Multi-Component Mixtures Terpene Mixture 1 Terpene Mixture 2 Item No. 25928 Item No. 25929 · A 21-component mixture of terpenes that · A 21-component mixture of terpenes that can be isolated from Cannabis can be isolated from Cannabis · Contains 1 mg/ml of each compound, · Contains 1 mg/ml of each compound, including β-myrcene, linalool, β-, including (+)-limonene, α-humulene, and (–)-caryophyllene oxide α-pinene, and (–)-β-pinene · Includes a certified concentration and · Includes a certified concentration and uncertainty value for each analyte uncertainty value for each analyte Single-Component Standards

Item No. Product Name Item No. Product Name

14007 (+)-Aphidicolin 23172 (−)-Guaiol

9002495 (–)-α-Bisabolol 21574 α-Humulene

23467 (+)-Borneol 14620 (−)-Huperzine A

23468 (−)-Borneol 23161 (−)-Isopulegol

24478 (±)-Camphene 21719 (+)-Limonene

21572 β-Caryophyllene 21575 (±)-Linalool

21573 (−)-Caryophyllene oxide 23463 (+)-Menthol

23464 (+)-β-Citronellol 21720 β-Myrcene

25770 α-Copaene 25774 Nerol

23159 p-Cymene 11345 Paxilline

25126 23-epi-26-Deoxyactein 23179 α-Phellandrene

19641 β-Elemene 21576 α-Pinene

22183 Eucalyptol 21577 (−)-β-Pinene

25771 β-Eudesmol 25777 Sabinene

23162 (+)-Fenchol 23722 γ-Terpinene

11018 Forskolin 23173 Terpineol

22184 Geranyl Acetate 21712 Terpinolene

View a complete list of our terpene standards at www.caymanchem.com For custom quantities or formulations, please email [email protected]

www.caymanchem.com · (800) 364-9897 Mycotoxins Test for the presence of mycotoxins produced by fungi that have been found in Cannabis samples and cultivation materials using Cayman’s mycotoxin mixture and single-component standards.

NEW: Mycotoxin Mixture 5 (CRM) Item No. 28151

· Contains aflatoxin B1, B2, G1, G2, and ochratoxin A at 10 μg/ml of each compound · Includes a certified concentration and uncertainty value for each analyte · Intended for use as a calibration or quality control standard

Testing a larger panel of mycotoxins? Discover our collection of standards for aflatoxins, ochratoxins, and sterigmatocystins at www.caymanchem.com

Pesticides Residual Solvents Multi-Component Mixtures Single-Component Standards

· Contain 8-16 pesticides per mixture at Item No. Product Name

100 μg/ml of each compound 25932 Butane Residual Solvent Standard

· Include a certified concentration and 25933 Isobutane Residual Solvent Standard

uncertainty value for each analyte 25934 Propane Residual Solvent Standard · Intended for use as a calibration or quality control standard EXPLORE Item No. Product Name

26192 Pesticide Mixture 1 - 16 Components APPLICATION

26193 Pesticide Mixture 2 - 15 Components NOTES

26194 Pesticide Mixture 3 - 15 Components

26195 Pesticide Mixture 4 - 15 Components Comparison of CRM Concentrations Among 26196 Pesticide Mixture 5 - 14 Components Four Different Reference 26197 Pesticide Mixture 6 - 15 Components Material Producers 26198 Pesticide Mixture 7 - 8 Components

26199 Pesticide Mixture 8 - 15 Components CRM Mixtures Improve Quantitation Accuracy

26200 Pesticide Mixture 9 - 16 Components

26201 Pesticide Mixture 10 - 15 Components www.caymanchem.com/literature

View a complete list of our mycotoxin, pesticide, and residual solvent standards at www.caymanchem.com

1180 East Ellsworth Road · Ann Arbor, MI · 48108 · USA Synthetic cannabinoids designed to mimic the effects of THC have appeared in herbal products. Cayman offers DEA exempt preparations of classic and emerging synthetic compounds as well as a high-throughput mixture to rapidly screen for synthetic cannabinoid adulterants.

Synthetic Cannabinoid Screening Library Item No. 9002891 · Contains >350 synthetic cannabinoids in five 96-well plates · Includes parent compounds and their positional isomers, analogs, and homologs · Supplied in a 96-well Matrix tube rack format as 10 mM stocks in DMSO Single-Component Standards

Item No. Product Name

Common Synthetic Cannabinoid Laboratory Guide for Mass Spectrum of MS Fragments MMB-FUBINACA m/z = 386-304 SYNTHETIC 27237 AB-CHMINACA (CRM) Cl F Cl O O O O O O NH NH NH NH NH F m/z = 109 N N N N N N 109 N N N N N CANNABINOID Abundance N 1800000 O F F F F 1700000 m/z = 253 m/z: 386 m/z: 372 m/z: 370 m/z: 368 m/z: 362 Identification and Naming 253 1600000

1500000

1400000 F 1300000 O O O O O O O NH NH NH NH NH NH NH 1200000 O NH 1100000 N N N N N N N 1000000 N N N N N N N N N 19805 4-fluoro ADB (CRM) 900000 F F F F 800000 F m/z: 360 m/z: 352 m/z: 352 m/z: 352 m/z: 352 m/z: 345 N m/z: 338 700000 m/z = 324 OMe O 324 600000 O O NH PERPETRATOR 500000 N 400000 N N H N O O O O O O NH NH NH NH NH NH 300000 m/z = 145 269 145 200000 83 F m/z = 383 N N N N N N 100000 43 OMe 59 102 225 383 N 71 90 130 N N N N N 51 117 159 172179186 196 207 215 235242 281 309 331 341 352 0 m/z--> 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 360 370 380 390 F F m/z: 334 m/z: 326 m/z: 324 m/z: 320 m/z: 320 HEAD m/z: 338 Tips for GC-MS Interpretation: O Swapping the synthetic cannabinoid core: O O O O O 27043 AM2201 (CRM) NH NH NH NH NH · The difference in mass (m/z) for the indole version of a comparable indazole is -1. O N N N N N Here are some common substituents to replace an H (such as where R is N N N N N NH noted in the Common MS Fragments section above): F F · If R = CH , the m/z is +14 · If R = CH CH , the m/z is +28 m/z: 318 m/z: 312 m/z: 308 m/z: 306 m/z: 304 3 2 3 · If R = F, the m/z is +18 · If R = OCH3, the m/z is +30 CORE · If R = CN, the m/z is +25 · If R = Cl, the m/z is +34 N Common Synthetic Cannabinoid N Synthetic Cannabinoid Naming Chart MS Fragments 28624 APP-BUTINACA (CRM) m/z = 304-100 HEAD GROUPS

NH2 NH2 NH2 NH2 TAIL NH2 OMe F A = AB = O ADB = APP = MPP = AMP = AEP = O O O O O O R HN Except: O Also: MPhP O O NH NH NH NH NH N MAB-CHMINACA HN O O HN HN H HN HN N N N N N N N N N N N N N OEt OEt · R=H, CUMYL = N N N F CYP = N N PY = MEPIRA = BEPIRA = EMP = EDMB = F H · R=F, 4F-CUMYL = H N O O m/z: 304 m/z: 300 m/z: 298 m/z: 290 m/z: 286 R=H, m/z: 285 HN HN MMB-FUBINACA · R=Cl, 4Cl-CUMYL = R R Systematic Name: MMB-FUBINACA DEA Schedule: Schedule I HN OEt OMe OMe OMe HO HO O HO HO O HO O EADB = EMB = MMB = MDMB = · R=H, MMP = NA = QU = N N N NH NH N NH Synonyms: AMB-FUBINACA, FUB-AMB DEA No.: DEA 7021 O Also: AEB O Also: O Also: ADB O O HN HN MAB, AMB, MA HN HN · R=CH3, MEP = HN Molecular Weight: 383.4 Date of Fed Schedule: Nov. 3rd, 2017 O 19948 CUMYL-PINACA (CRM) N N N N N N N N N N N N N Cayman Item No.: 9001960

F F F F O m/z: 280 m/z: 272 m/z: 272 m/z: 269 m/z: 254 m/z: 253 m/z: 249 m/z: 243 CORE GROUPS O O O O O O NH N O O O HO HO O O O NH O 4 NH 4 NH NH NH NH 5 INACA = ICA = IC = GACLONE = 5-AICA = N 7-AICA = 5 N N N N N N N N N N N N 6 N 1 6 N N 1 N N N N N N N N 7 7 O F F O NH O NH 3 O O m/z: 241 m/z: 235 m/z: 233 m/z: 231 m/z: 229 m/z: 227 m/z: 226 N m/z: 219 O 5 NH INAC = O 3,5-FUPPYCA = 1 5,3-FUPPYCA = IM = INAM = CZCA = Also: N N FUPYCA, 5 N1 O O N FUPPYCA 3 N N O O O HO O N N N F 27973 JWH 018 (CRM) N F N N N N N N N N N N H R OMe m/z: 215 m/z: 213 m/z: 201 m/z: 197 R=H, m/z: 155 m/z: 145 m/z: 135 TAIL GROUPS

OMe www.caymanchem.com CHM = BUT = 4CN-BUT = 4F-BUT = FUB = B = N Also: CH, CH-Me Also: B Also: 4CN-B, CN Also: 4F-B F CYB, CB-P F O N N F H R m/z: 135 R=H, m/z: 127 m/z: 121 m/z: 117 m/z: 109 m/z: 100 PIPET = N P = 4en-P = 5F-P = THP = Also: Pe Also: PEN O F

Our online Synthetic Cannabinoid Flipbook Tool can be found at www.caymanchem.com/flipbook 22047 MAB-CHMINACA (CRM) © 2018 Cayman Chemical · Revised July 2019

28186 4-fluoro MDMB-BUTINACA (CRM)

18203 PB-22 (CRM) Request the Synthetic Cannabinoid

ISO60055 UR-144 (CRM) Lab Guide wall poster at

ISO60059 XLR11 (CRM) www.caymanchem.com/literature

Other Cannabinoids of Interest Single-Component Standards

Item No. Product Name Item No. Product Name

29031 CBDB 29780 (6aR,9R)-Δ10-THC (exempt preparation)

29306 Δ9-THCB 29781 (6aR,9S)-Δ10-THC (exempt preparation)

30169 CBDP 29779 9(R)-Δ6a,10a-THC (exempt preparation)

30171 Δ9-THCP 29782 9(S)-Δ6a,10a-THC (exempt preparation)

View a complete list of more than 750 cannabinoid standards at www.caymanchem.com

DEA exempt applies to US only. Products may be controlled in other countries. Please verify with your local distributor.

www.caymanchem.com · (800) 364-9897 High-Throughput Sample Preparation Precellys® Evolution from Bertin Technologies Grind, lyse, and homogenize samples in less than 30 seconds!

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Plant Extraction Application Notes DNA Extraction from Rice Leaf Mycoviral double-stranded RNA extraction from plant leaf with Minilys Protein extraction from Nicotiana benthamiana leaf To request a copy, email [email protected] Cayman Chemical is a proud distributor of Bertin Instruments’ homogenizers and consumables in the United States. Learn more at www.caymanchem.com/Precellys

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