Tetrahydrocannabivarin

Base Information

• Chemical Name: Tetrahydrocannabivarin
• CAS No.: 31262-37-0
• Molecular Formula: C19H26 O2
• Molecular Weight: 286.414
• European Community (EC) Number: 809-026-4
• UNII: I5YE3I47D8
• DSSTox Substance ID: DTXSID10893920
• Nikkaji Number: J108.077F
• Wikipedia: Tetrahydrocannabivarin
• Wikidata: Q76009679
• Pharos Ligand ID: FRBCZQT6U93F
• Metabolomics Workbench ID: 144421
• ChEMBL ID: CHEMBL2387541
• Mol file: 31262-37-0.mol

Synonyms:TETRAHYDROCANNABIVARIN;31262-37-0;delta9-Tetrahydrocannabivarin;THCV;THC-V;.delta.9-Tetrahydrocannabivarin;(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;GWP42004;GWP-42004;UNII-I5YE3I47D8;I5YE3I47D8;O-4394;Cannabivarol, .delta.9-tetrahydro-;(-)-.delta.9-trans-Tetrahydrocannabivarin;6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR-trans)-;6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (-)-;6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR-trans)-;6H-DIBENZO(B,D)PYRAN-1-OL, 6A,7,8,10A-TETRAHYDRO-6,6,9-TRIMETHYL-3-PROPYL-, (6AR,10AR)-;6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR,10aR)-;Delta9-THCV;D0D8PZ;.delta.9-Tetrahydrocannabivarol;GTPL6418;SCHEMBL6856739;CHEMBL2387541;.delta.1-Tetrahydrocannabidivarol;DTXSID10893920;BDBM50511105;HY-U00342;.delta.9-trans-Tetrahydrocannabivarin;Cannabidivarol, .delta.1-tetrahydro-;AKOS040762420;CS-7377;DB11755;Delta9-Tetrahydrocannabivarin (THCV) 10 microg/mL in Methanol;delta9-Tetrahydrocannabivarin (THCV) 100 ug/mL in Methanol;delta9-Tetrahydrocannabivarin (THCV) 1000 ug/mL in Methanol;(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;(6AR,10AR)-6,6,9-TRIMETHYL-3-PROPYL-6H,6AH,7H,8H,10AH-BENZO[C]ISOCHROMEN-1-OL;6,6,9-Trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol-, (6aR-trans)-

Chemical Property of Tetrahydrocannabivarin

Chemical Property:

• Vapor Pressure: 1.06E-05mmHg at 25°C
• Boiling Point: 360.6°Cat760mmHg
• PKA: 9.79±0.60(Predicted)
• Flash Point: 137.6°C
• PSA: 29.46000
• Density: 1.034g/cm³
• LogP: 4.95560
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 286.193280068
• Heavy Atom Count: 21
• Complexity: 412

Purity/Quality:

≥97% ^*data from raw suppliers

Tetrahydrocannabivarin (CRM) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O
• Isomeric SMILES: CCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O
• Recent ClinicalTrials: A Study of GWP42004 as Add on to Metformin in the Treatment of Participants With Type 2 Diabetes
• Recent EU Clinical Trials: A randomised, double blind, placebo controlled, parallel group, dose ranging study of GWP42004 as add on to metformin in the treatment of participants with Type 2 diabetes.
• Description: Tetrahydrocannabivarin (CRM) (Item No. 18091) is a certified reference material categorized as a phytocannabinoid. This product is intended for research and forensic applications.

Technology Process of Tetrahydrocannabivarin

There total 8 articles about Tetrahydrocannabivarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,4-dihydroxy-6-n-propylbenzoic acid, methyl ester (55382-52-0) → tetrahydrocannabivarin (31262-37-0,28172-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / toluene / 20 °C

1.2: 0.42 h / 20 °C

2.1: potassium hydroxide / 2 h / 100 - 120 °C / 375.04 Torr

3.1: 150 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0.22 °C

With boron trifluoride diethyl etherate; potassium hydroxide; In dichloromethane; toluene;

Reference yield:

Δ9-tetrahydrocannabivarin tosylate (1179328-06-3) → tetrahydrocannabivarin (31262-37-0,28172-17-0)

Guidance literature:

With potassium tert-butylate; water; In tert-butyl alcohol; at 65 ℃; for 4.5h;

Reference yield:

cannabidivarin (24274-48-4) → tetrahydrocannabivarin (31262-37-0,28172-17-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0.22 ℃; for 0.5h;

upstream raw materials:

5-propyl-1,3-benzenediol

cis-Δ²-p-menthene-1,8-diol

Δ9-tetrahydrocannabivarin tosylate

2,4-dihydroxy-6-n-propylbenzoic acid, methyl ester

Downstream raw materials:

Δ9-tetrahydrocannabivarin tosylate

cannabivarin

Δ⁹-tetrahydrocannabivarin-11-oic acid

Refernces

A concise methodology for the synthesis of (-)-Δ⁹-tetrahydrocannabinol and (-)-Δ⁹-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

10.1016/j.tet.2007.06.006

The research aims to develop an efficient and concise method for synthesizing metabolites of tetrahydrocannabinols (THC) and tetrahydrocannabivarin (THCV), including their deuterated forms, which are crucial for analyzing biological and toxicological samples. The study introduces a streamlined synthetic approach using commercially available starting materials, such as (+)-(1R)-nopinone, to obtain key intermediates in just four steps. The methodology employs an optimized Shapiro reaction and avoids undesirable oxidative conditions, resulting in significantly improved overall yields and high optical purity. The researchers successfully synthesized eight regiospecifically deuterated metabolites without deuterium scrambling or loss, demonstrating the method's efficiency and applicability for preparative-scale production. This work provides a valuable tool for future studies on the biological and toxicological effects of these compounds.

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