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

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

Uses

Used in Pharmaceutical Industry:
THCA is used as a therapeutic agent for its potential anti-inflammatory properties, which may help in reducing inflammation associated with various conditions.
Used in Neuroprotective Applications:
In the field of neurology, THCA is utilized as a neuroprotective agent, potentially safeguarding the nervous system and offering benefits in treating neurodegenerative diseases.
Used in Oncology:
THCA is considered for use as an anticancer agent, with ongoing research exploring its potential to treat cancer by targeting and reducing tumor growth.
Used in Epilepsy Treatment:
In the treatment of epilepsy, THCA is used for its potential anticonvulsant properties, which may help in managing seizures and reducing their frequency.
Used in Antiemetic Therapy:
THCA is employed as an antiemetic agent, particularly for managing nausea and vomiting associated with chemotherapy in cancer patients.
While the provided materials do not explicitly list the uses of THCA in different industries, the above applications are inferred from the potential therapeutic benefits mentioned. Further research and development may reveal additional uses across various industries as the understanding of THCA's properties expands.

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

• 105539-75-1 (trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid methyl ester 
• 105539-71-7 (trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carbonitrile 
• 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.

Compounds having improved fluorescence in fluorescence polarization immunoassays and immunoassays utilizing same

Compounds of the formula STR1 wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.