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Cannabis Testing Standards.Pdf Cannabis Testing Standards As the Cannabis 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 cannabichromene → 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-Tetrahydrocannabinol (Δ8-THC) OH 6 2 5 7 OH OH OH Cannabidiol (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 Cannabicyclol (CBL) 1 1 2' 5 3 HO 7 6a 7 6a 4 4 2' (22036 | 9002438) 10a 2 10a 2 1' 1' Cannabigerol (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 Cannabinodiol (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 CannaBiNol 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) Cannabielsoin (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 Cannabigerolic Acid (CBGA) (E isomer) synthase Cannabichromenic Acid (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 olivetolic acid 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 Cannabinoids. 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 Cannabidivarin (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-Tetrahydrocannabivarin (THCV) (Δ9-THCV) Δ -Tetrahydrocannabiorcin (THCO) (Δ -THCO) Cannabinerorcin (CBNRO) (Z isomer) Cannabinerovarin (CBNRV) (Z isomer) 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 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) Cannabivarin (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.
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