Basic information
- CAS
23978-85-0- Standard SMILES
CCCCCc1cc2c(c(O)c1C(=O)O)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2- InChIKey
UCONUSSAWGCZMV-HZPDHXFCSA-N- Molecular formula
- C22H30O4
- Average molar mass
- 358.5 g/mol
- Monoisotopic mass
- 358.21440943
Overview
Delta(9)-tetrahydrocannabinolic acid is a diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to 9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. It has a role as a metabolite, a biomarker, a neuroprotective agent and an anti-inflammatory agent. It is a diterpenoid, a polyketide, a hydroxy monocarboxylic acid, a benzochromene and a phytocannabinoid. It is a conjugate acid of a Delta(9)-tetrahydrocannabinolate.
Names & identifiers
- Preferred name
- delta9-Tetrahydrocannabinolic acid
- IUPAC
- (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
- English name
- Delta9-Tetrahydrocannabinolic acid A solution
- Molecular formula
- C22H30O4
- Molecular weight
- 358.47
Names & synonyms
23978-85-0delta(9)-Tetrahydrocannabinolic acid9-Carboxy-thcTHCA-A9-Carboxy-delta(9)-thcDelta9-tetrahydrocannabinolic acidThc-9-coohEJ6CZV0K5YCHEBI:67078(6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6h-benzo[c]chromene-2-carboxylic acid6H-Dibenzo(b,d)pyran-2-carboxylic acid, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-6H-Dibenzo(b,d)pyran-2-carboxylic acid, 6abeta,7,8,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-
Show more names
TetrahydrocannabinolsTHCA-A (CRM)Dea no. 7370THCA-A (Alt. Batch CRM)Tetrahydrocannabinol acidTHCA-A (exempt preparation)
THCA-A compound(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromene-2-carboxylic acidRefChem:34411Delta-9-Tetrahydrocannabinolic aciddelta9-tetrahydrocannabinolic acid A(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acidDelta9-tetrahydrocannabinolateUNII-EJ6CZV0K5Y
Properties
Computed structural properties
- XLogP
- 7
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 552
Experimental & physicochemical properties
Chemical ClassesStimulant
DrugsPharmaceuticals -> Illicit drugs
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 70 °C · 70 °C (decomp)
- Boiling point
- 436.8 · 436.8±45.0 °C(Predicted)
- Density
- 1.112 · 1.112±0.06 g/cm3(Predicted)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- -20 °C · -20°C
- solubility
- 50 mg/ml; · DMF: 50 mg/ml; DMF:PBS (pH 7.2) (1:3): 0.25 mg/ml; DMSO: 60 mg/ml; Ethanol: 35 mg/ml; Methanol: 30 mg/ml
- pka
- 3.32 · 3.32±0.60(Predicted)
- FDA UNII
- 6 CZV0K5Y · EJ6CZV0K5Y
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 1648 3 / PGII
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Hazard statements
- H225-H302+H312+H332-H319
- Precautionary statements
- P210-P280-P305+P351+P338
- DEA Controlled Substances
- CSCN: 7370CAS SCH: I NARC: N
Chemistry & industry
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesDelta9-Tetrahydrocannabinolic acid A solution (THCA-A) is a non-psychoactive acidic cannabinoid found in cannabis with anti-inflammatory, neuroprotective, and anticancer effects. It is also the precursor to the major psychoactive cannabinoid found in cannabis, known as Δ-9-tetrahydrocannabinol (Δ-9-THC). Δ9-Tetrahydrocannabinol (THC) is a quantitative analyte that can be used for oral fluid cannabinoid monitoring.THCA-A is available as a DEA-exempt preparation and is registered as a Canadian test kit. It is primarily used in chemical analysis studies and forensics.
Suppliers12 total
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
ARCTIC EXPORTS INC+1-3026880818 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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