Basic information
- CAS
25555-57-1- Standard SMILES
CCCCCc1cc(O)c(C/C=C(\C)CCC=C(C)C)c(O)c1C(=O)O- InChIKey
SEEZIOZEUUMJME-FOWTUZBSSA-N- Molecular formula
- C22H32O4
- Average molar mass
- 360.5 g/mol
- Monoisotopic mass
- 360.2300595
Overview
Cannabigerolic acid is a dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to 9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. It is a dihydroxybenzoic acid, a diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It is functionally related to an olivetolic acid. It is a conjugate acid of a cannabigerolate.
Names & identifiers
- Preferred name
- Cannabigerolic Acid
- IUPAC
- 3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-pentylbenzoic acid
- English name
- cannabigerolic acid
- Molecular formula
- C22H32O4
- Molecular weight
- 360.49
Names & synonyms
Cannabigerolic acid25555-57-180I4ZM847YCHEBI:67081DTXSID401315426(E)-3-(3,7-Dimethyl-2,6-octadienyl)-2,4-dihydroxy-6-pentylbenzoic acid3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-pentylbenzoic acid3-((2E)-3,7-dimethylocta-2,6-dienyl)-2,4-dihydroxy-6-pentylbenzoic acidRefChem:5642DTXCID501745335CBGAUNII-80I4ZM847Y
Show more names
cannabigerolicaci(E)-Cannabigerolic AcidCannabigerolic Acid (CRM)Cannabigerolic acid solutionCannabigerolic Acid (Alt. Batch CRM)Cannabigerolic acid (CBGA) in AcetonitrileCannabigerolic acid (CBGA) 100 μg/mL in Acetonitrile
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acidBenzoic acid, 3-(3,7-dimethyl-2,6-octadienyl)-2,4-dihydroxy-6-pentyl-, (E)-Cannabigerolic acid (CBGA)SEEZIOZEUUMJME-FOWTUZBSSA-NA1CGBCHEMBL463843orb1690779SCHEMBL9909324
Database identifiers
- CAS
25555-57-1- PubChem CID
- 6449999
- DTXSID
DTXSID401315426- ChEMBL
CHEMBL463843- ChEBI
CHEBI:67081- UNII
- 80I4ZM847Y
- EC Number
- 950-268-6
- Nikkaji
- J19.302J
Properties
Computed structural properties
- XLogP
- 7.5
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 10
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 490
Experimental & physicochemical properties
DrugsDEA NFLIS-Drug Category -> Cannabinoids
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Other aromatic polyketides [PK1312]
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Boiling point
- 535.7 · 535.7±50.0 °C(Predicted)
- Density
- 1.082 · 1.082±0.06 g/cm3(Predicted)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- -70 °C · -70°C
- pka
- 3.42 · 3.42±0.43(Predicted)
- form
- A neat solid
- Major Application
- cannabis testingcannabis testing
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - MISCELLANEOUS
- InChI
- 1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)/b16-12+
- InChIKey
- SEEZIOZEUUMJME-FOWTUZBSSA-N
- SMILES
- Oc1c(c(cc(c1C(=O)O)CCCCC)O)C\C=C(\CCC=C(C)C)/C
- FDA UNII
- 80 I4ZM847Y · 80I4ZM847Y
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302+H312+H332-H319
- Precautionary statements
- 210 · P210-P261-P280-P305+P351+P338-P370+P378-P403+P235
- RIDADR
- 1648 · UN 1648 3 / PGII
- WGK Germany
- 2 · 2
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 60% (3 of 5) of all reports.
Warning
H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32802
Hazard Classes and CategoriesAcute Tox. 4 (40%)
Safety data
- wgk
- 2
- ridadr
- UN 1648 3 / PGII
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225-H302+H312+H332-H319
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P261-P280-P305+P351+P338-P370+P378-P403+P235
Chemistry & industry
Applications
Usescannabigerolic acid (CBGA), a major biosynthetic precursor molecule in cannabis,exhibits divergent effects on seizures in mouse models of epilepsy. CBGA is generated from geranyl pyrophosphate and olivetolic acid by Cannabis sativaprenyltransferase (CsPT4).
General DescriptionA non-psychoactive cannabinoid, cannabigerolic acid (CBGA), is the precursor to THCA, CBDA, and CBCA cannabinoids in Cannabis. Cannabigerolic acid reportedly has efficacy in treatment of cancer and schizophrenia. This Certified Spiking Solution is suitable for CBGA testing methods by HPLC, LC/MS, or GC/MS for applications in testing of Cannabis potency or impurity profiling, pharmaceutical research, and forensic analysis. Cerilliant solution Certified Reference Materials (CRMs) of cannabinoids are supplied in a convenient, quantitative, US DEA-exempt solution format and with TK#s for Canadian customers.
Suppliers17 total
成都健腾生物技术有限公司028-85159085 · [email protected]
深圳创元生物医药科技有限公司0755-26916280 13602537306
上海九芳科技有限公司021-61150629 15921749159 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
泰州布莱泽生物医药科技有限公司0523-86112008 13915404123 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
泰州布莱泽生物医药科技有限公司0523-86112008 13915404123 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318584237 · [email protected]
上海莫奇生物科技有限公司13341702378 · [email protected]
厦门沃克沃德医药科技有限公司15921822462 15921822462 · [email protected]
Additional notes
DefinitionChEBI: Cannabigerolic acid is a dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. It is a dihydroxybenzoic acid, a diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It is functionally related to an olivetolic acid. It is a conjugate acid of a cannabigerolate.
Related reactions
3 records
Compound notes
Loading…