39690-06-7

Basic information

• Product Name: TETRAHYDROCANNABINOL-7-OIC ACID
• Synonyms: TETRAHYDROCANNABINOL-7-OIC ACID;11-NOR-DELTA8-TETRAHYDROCANNABINOL-9-CARBOXYCLIC ACID;11-NOR-DELTA(8)-TETRAHYDROCANNABINOL-9-CARBOXYLIC ACID;11-CARBOXY-DELTA(8)-TETRAHYDROCANNABINOL;(-)-9-NOR-9-CARBOXY-DELTA8-TETRAHYDROCANNABINOL;11-NOR-DELTA-8-TETRAHYDROCANNABINOL-9- C;delta(6)-tetrahydrocannabinol-7-oic acid;11-Nor-Δ8-tetrahydrocannabinol-9-carboxylic acid solution
• CAS NO: 39690-06-7
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44
• Mol File: 39690-06-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 459.2 °C at 760 mmHg
• Flash Point: 154.8 °C
• Appearance: /vacuum-dried powder
• Density: 1.14 g/cm³
• Storage Temp.: −20°C
• PKA: 4.75±0.40(Predicted)
• CAS DataBase Reference: TETRAHYDROCANNABINOL-7-OIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDROCANNABINOL-7-OIC ACID(39690-06-7)
• EPA Substance Registry System: TETRAHYDROCANNABINOL-7-OIC ACID(39690-06-7)

Safety Data

• Statements: 23/24/25-36/38-39/23/24/25
• Safety Statements: 7-16-24-33-36/37-45
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 39690-06-7(Hazardous Substances Data)

Usage

General Description

Tetrahydrocannabinol-7-oic acid (THCA) is a non-psychoactive compound found in the cannabis plant. It is the precursor to the psychoactive compound, tetrahydrocannabinol (THC). When cannabis is heated, THCA undergoes a process called decarboxylation, converting it into THC, which is responsible for the psychoactive effects of marijuana. THCA has been studied for its potential therapeutic benefits, including its anti-inflammatory, neuroprotective, and antiemetic properties. It also has potential use in treating conditions such as cancer, epilepsy, and neurodegenerative diseases. However, more research is needed to fully understand the medical potential of THCA.

InChI:InChI=1/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h8,10-11,15-16,22H,4-7,9,12H2,1-3H3,(H,23,24)/t15-,16-/m1/s1

Synthetic route

carbon dioxide (124-38-9) + C35H52N2O4S (949595-94-2) → (6aR,10aR)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol + D8-THC-11-oic acid (39690-06-7) + 11-nor-9-carboxt-Δ-9-tetrahydrocannabinol (36557-05-8, 56354-06-4, 64280-14-4, 104874-50-2, 114028-39-6, 122797-75-5) + 9-Nor-D8-tetrahydrocannabinol (52171-84-3)

Conditions	Yield
Stage #1: C35H52N2O4S With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 0℃; for 1.5h; Shapiro reaction; Stage #2: carbon dioxide In hexane at 0℃; for 0.166667h; Further stages.;	A n/a B n/a C 183 mg D n/a

CH2 Cl2 -petroleum ether + 11-nor-Δ8-tetrahydrocannabinol-9-carboxylic acid methyl ester (51263-84-4) → D8-THC-11-oic acid (39690-06-7)

Conditions	Yield
With sodium hydroxide In methanol; water

Upstream product

• 105539-71-7 (trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carbonitrile 
• 105539-75-1 (trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid methyl ester 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 51263-84-4 (trans-rac)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid methyl ester 
• 51263-84-4 11-nor-Δ⁸-tetrahydrocannabinol-9-carboxylic acid methyl ester 
• 124-38-9 carbon dioxide 
• 949595-94-2 C₃₅H₅₂N₂O₄S 

Relevant articles and documents

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

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.

A convenient synthesis of 11-nor-Δ8-tetrahydrocannabinol-9-carboxylic acid

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