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Cannabis Testing Standards Cannabis Testing Standards Cayman Chemical has nearly four decades of experience in producing high-quality analytical standards. Our background in cannabinoid receptor research and synthesis of highly qualified reference standards for forensic analysis has led to our growing catalog of standards for Cannabis quality testing. From quantifying cannabinoids to identifying the presence of harmful contaminants, our standards will give you the tools to meet the requirements for Cannabis quality testing. PHYTOCANNABINOIDS TERPENES ACCELERATE WORKFLOWS & REDUCE PROCESSING RESIDUAL SOLVENTS COSTS, VARIABILITY, AND TIME! PESTICIDES & MYCOTOXINS www.caymanchem.com · Toll Free (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 The two most common conventions for numbering THC are the dibenzopyran and 4 drives the name and acronym of each compound. The resorcinol root will designate the original C5 monoterpene systems.1,2 The biphenyl and Lord Alexander Todd numbering series and its C3 and C1 homologs. Listed here are the main scaffolds observed in phytocannabinoids. CLASSIC OLIVETOL SERIES systems are older and less common.1,2 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.2,3 –NOL, with a few exceptions. When describing the C3 and C1 homologs, the scaffold name is amended Olivetolic phytocannabinoids are considered classic, as these are by dropping the -OL and replacing the suffix with -VARIN/VARINOL (C3) or -ORCIN/ORCINOL (C1). the compounds that are ubiquitous to all varietals of marijuana. This The oricinolic series is unique in that the suffix has also been placed within the scaffold name Most Common Systems (-ORC- as in cannabichromene → cannabiorcochromene). series is not only the most dominant in the Cannabis species but Dibenzopyran Numbering Monoterpene Numbering also the most widely studied in the literature. 11 7 Resorcinol Root Name 9 6 8 10 1 OH OH 6 2 5 7 OH OH OH H 1 5 3 8 6a 2' 7 4 4 2' OH 10a 2 1' 3 3' 1' H 3' OH 8 2 HO HO HO 3 O 6 O 6' 6' 4' 4' Olivetol Divarin Orcinol 8 8 5 4 10 9 1 Δ -Tetrahydrocannabinol (Δ -THC) 7 5' 5' 11 11 7 -OL -VARIN, -VARINOL -ORCIN, -ORCINOL, -ORC- (ISO60158 | 14042) HO HO Cannabidiol (CBD) 9 9 O 8 10 8 10 OH Cannabigerol (CBG) (E isomer) (ISO60156 | 90080) OH OH 2 6 Main Scaffold Motifs and Names H H 5 3 (20164 | 15293) 1 1 2' 5 3 OH 7 6a 7 6a 4 4 2' Cannabinerol (CBNR) (Z isomer) 10a 2 10a 2 1' 1' 3' 3' Monocyclic Bicyclic Tricyclic Tetracyclic H H O 8 8 3 3 6' 6 O 6 O 4' 6' OH 9 9 H 9 4' OH Δ -Tetrahydrocannabinolic Acid A (THCA-A) (Δ -THCA-A) OH 5 4 5 4 10 10 9 OH OH H 5' 5' OH O (ISO60175) Δ8 Δ9 Δ6 Δ1(2) OH H Monoterpene numbering designates the dibenzopyran Δ8 HO R O R OH O Dibenzopyran numbering designates the double bond of O R O 6 9 1 2 OR HO R O OH 8 9 configuration as Δ . The dibenzopyran Δ configuration is Δ (or Δ ). CannaBiGerol interest as Δ or Δ . CannaBiChromene 9 9 OH CBG CannaBiNol iso-TetraHydroCannabinol CannaBicycLol Δ -Tetrahydrocannabinol (THC) (Δ -THC) Cannabicyclol (CBL) CBC CBN iso-THC CBL (ISO60157 | 12068) HO (22036 | 9002438) O HO Cannabinodiol (CBND) Older/Less Common SystemsTerpenoid System HO OH Cannabidiolic Acid (CBDA) (9002479) OH OH OH O O OH (18090) Biphenyl Numbering Terpenoid Numbering Δ9-Tetrahydrocannabinolic Acid B (Δ9-THCA-B) OH 10' 9' 1' 1 OH R OR O R HO HO 10' 6 OR HO 2 HO 3 2' 5' 1' 1 OH 7' OH 4 2 6 CannaBiciTran 3' 2 TetraHydroCannabinol CannaBiTriol OH 7' 5' CannaBiDiol OH 5 1 3' 5 3 8' 6' 4' 2' ‘Citran’ CBT O 2' THC ‘Triol’ CBT 6 O CBD 1' 8' 4' 4 5 3 3' 6' 9' HO HO 4 Cannabichromene O 6' 4' Cannabigerol O HO (CBC) OH O O OH 5' (CBG) Cannabitriol (CBT) (triol) Cannabiripsol (CBR) THCA CBDA Cannabielsoin (CBE) 7 Todd Numbering synthase synthase HO R 1 O R R H HO HO O 6 2 1' OH HO OH 2' H O 7' 5 3 6' 1 CannaBiNoDiol CannaBiElsoin CannaBiFuran Cannabichromene (CBC) 5' 4 2' 6 6' 3' 5' 1' 2 CBND CBE CBF (ISO60163) 4' 6' 6" 4' H 3' 1' 8 5 2' 1" 5' 4' 3' 3 4 5" HO OH O HO O HO 3 5 10 9 4 OH exo-Tetrahydrocannabinol (exo-THC) 2 Cannabifuran (CBF) 1 4" Cannabielsoin Cannabicyclol O 2" 3" (CBE) (CBL) OH OH O OR OH O OH O anna i ipsol C B R OH OH 1. Mechoulam, R. and Gaoni, Y. Fortschr. Chem. Org. Naturst. 25, 175-213 (1967). CBR OH CBCA 2. ElSohly, M.A. and Slade, D. Life Sci. 78(5), 539-548 (2005). O O O HO 3. 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 Cannabinol (CBN) Cannabigerolic Acid (CBGA) (E isomer) synthase Cannabichromenic Acid (CBCA) Cannabinolic Acid (CBNA) (e.g., CBDM = cannabidiol methyl ester). “A” is indicative of the carboxylated (ISO60183) (20019 | 9001572) (9001573) O Cannabinerolic Acid (CBNRA) (Z isomer) olivetolic acid and is added to the very end of the acronym (e.g., THCA = tetrahydrocannabinolic acid). HO O OH 4. Brenneisen, R. Chemistry and analysis of phytocannabinoids and other Cannabis O Cannabicitran (CBT) (citran) constituents. In Marijuana and the Cannabinoids. 17-49, Totowa, US: Humana Press (2007). (21295) HO HO Cannabielsorcinol (CBEO) Cannabinodiorcin (CBNDO) OH O OH Heat, Light, and Biosynthesis O OH Oxidation Exposure geranyl- Enzymes Cannabinodivarin (CBNDV) HO HO transferase OH Cannabifuraorcin (CBFO) Cannabidiorcin (CBDO) Cannabifuravarin (CBFV) Also known as O-1821 (10006804) OH OH O O OH OH HO O OH HO OH Cannabidivarin (CBDV) ORCINOL SERIES HO HO (20165 | 9001574) OH VARINOL SERIES Cannabidiorcinic Acid (CBDOA) Cannabidivarinic Acid (CBDVA) Olivetolic Acid Orcinolic phytocannabinoids have been identified OH Varinolic cannabinoids were once rare but are now H OH H in Nepalese and Brazilian samples but are also found H O O H targets of selective breeding. They have also been H H O O O O as major compounds in non-Cannabis species OH exhibited in higher abundance in C. indica over C. sativa. Cannabicyclorcinol (CBLO) Cannabicitraorcin (CBTO) (citran) Cannabicitravarin (CBTV) (citran) Cannabicyclovarin (CBLV) such as Rhododendron. O O CoA-S Hexanoyl-CoA OH OH OH Cannabielsovarin (CBEV) OH OH OH O OH OH O OH OH HO OH O O O O OH O O O O Δ9-Tetrahydrocannabiorcin (THCO) (Δ9-THCO) Δ8-Tetrahydrocannabiorcin (Δ8-THCO) Δ8-Tetrahydrocannabivarin (Δ8-THCV) Δ9-Tetrahydrocannabivarin (THCV) (Δ9-THCV) Cannabichromeorcinic Acid (CBCOA) Cannabichromeorcin (CBCO) Cannabichromevarin (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 HOOH HO OH OH OH O O OH HO OH O O OH HO O O O O OH OH HO OH geranyl- OH geranyl- HO CoA-S S-CoA HO 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) Cannabigerovarinic Acid (CBGVA) (E isomer) Cannabitrivarinol (CBTV) (triol) Cannabiripsovarinol (CBRV) 9 9 Orcinolic Acid 9 Δ -Tetrahydrocannabiorcinic Acid (Δ -THCOA-A) (23258) OO Varinolic Acid (25469) Tetrahydrocannabivarinic Acid A (Δ -THCVA-A) Cannabinerorcinic Acid (CBNROA) (Z isomer) 3 x Cannabinerovarinic Acid (CBNRVA) (Z isomer) CoA-SOH OH OH O OH OH O OH OH OH HO HO OH O O O O Cannabigerorcin (CBGO) (E isomer) Cannabigerovarin (CBGV) (E isomer) Cannabinorcin (CBO) Cannabinorcinic Acid (CBOA) (23257) © 2018 Cayman Chemical (9002437) Cannabivarinic Acid (CBVA) Cannabivarin (CBV) Cannabinerorcin (CBNRO) (Z isomer) Revised June 2018 Cannabinerovarin (CBNRV) (Z isomer) (21664) A guide to the biosynthesis, naming, and numbering of phytocannabinoids Visit www.caymanchem.com/literature www.caymanchem.com · Toll Free (800) 364-9897 Phytocannabinoids Trust the manufacturing experience that comes with decades of synthesizing, purifying, and characterizing cannabinoid receptor ligands – from endocannabinoids to highly selective synthetics – for your potency testing. Single Standards & Mixtures Available as Certified Reference Materials (CRMs) Cayman’s CRMs are... · 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 · Given a certified property and uncertainty value for traceability INCLUDED IN MULTI-COMPONENT PHYTOCANNABINOID MIXTURES 3-Component Mix 5-Component Mix 6-Component Mix 10-Component Mix Item No. 23251 Item No. 25076 Item No. 25077 Item No. 21305 Item No. Product Name 1 mg/ml each 500 µg/ml each 500 µg/ml each 250 µg/ml each ISO60156 Cannabidiol (CRM) ISO60183 Cannabinol (CRM) ISO60157 Δ9-THC (CRM)* 18090 Cannabidiolic Acid (CRM) ISO60175 THCA-A (CRM) 20164 Cannabigerol (CRM) ISO60163 (±)-Cannabichromene (CRM)* 20165 Cannabidivarin (CRM) 20019 Cannabigerolic Acid (CRM) ISO60158 Δ8-THC (CRM)* 18091 Tetrahydrocannabivarin (CRM) 21974 (±)-Cannabichromevarin (CRM) Want to mix and match different cannabinoids in a mixture? 22036 (±)-Cannabicyclol (CRM) Email [email protected] for an estimate 21295 Cannabicitran (CRM) *Isotopically labeled standards are available for mass spec analysis View a complete list of our phytocannabinoid standards at www.caymanchem.com For custom quantities or formulations, please email [email protected] 1180 East Ellsworth Road · Ann Arbor, MI · 48108 · USA Terpenes Conveniently build a terpene profile for different strains of Cannabis using a pre-mixed solution containing commonly found terpenes – single standards are also available.
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