cannabidiolic acid

3-p-mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acid

CAS: 1244-58-2 C22 H30 O4 MW: 358.47790000

Identification

Namecannabidiolic acid
IUPAC2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
CAS Number1244-58-2
FDA UNIIFJX8O3OJCD
Molecular FormulaC22 H30 O4
Molecular Weight358.47790000
Nikkaji NumberJ14.354E

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 530.80 °C. @ 760.00 mm Hg (est)
Flash Point 552.00 °F. TCC ( 288.90 °C. ) (est)
logP (o/w) 7.870 (est)
Soluble in water, 0.003158 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for cannabidiolic acid usage levels up tonot for fragrance use.
Recommendation for cannabidiolic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

benzoic acid, 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-6-pentyl- CBDA 2,4- dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid 2,4- dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid 2,4- dihydroxy-3-[(1R,6R)-6-isopropenyl-3-methyl-2-cyclohexen-1-yl]-6-pentylbenzoic acid 3-p- mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acid 3-para- mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acid PubMed: Down-regulation of cyclooxygenase-2 (COX-2) by cannabidiolic acid in human breast cancer cells. PubMed: A comparison of cannabidiolic acid with other treatments for anticipatory nausea using a rat model of contextually elicited conditioned gaping. PubMed: [Medicinal chemistry and pharmacology focused on cannabidiol, a major component of the fiber-type cannabis]. PubMed: Suppression of lithium chloride-induced conditioned gaping (a model of nausea-induced behaviour) in rats (using the taste reactivity test) with metoclopramide is enhanced by cannabidiolic acid. PubMed: Motor effects of the non-psychotropic phytocannabinoid cannabidiol that are mediated by 5-HT1A receptors. PubMed: Effect of low doses of cannabidiolic acid and ondansetron on LiCl-induced conditioned gaping (a model of nausea-induced behaviour) in rats. PubMed: Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. PubMed: Cannabidiolic acid prevents vomiting in Suncus murinus and nausea-induced behaviour in rats by enhancing 5-HT1A receptor activation. PubMed: Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. PubMed: Heat exposure of Cannabis sativa extracts affects the pharmacokinetic and metabolic profile in healthy male subjects. PubMed: The hexanoyl-CoA precursor for cannabinoid biosynthesis is formed by an acyl-activating enzyme in Cannabis sativa trichomes. PubMed: The draft genome and transcriptome of Cannabis sativa. PubMed: The effects of cannabidiolic acid and cannabidiol on contractility of the gastrointestinal tract of Suncus murinus. PubMed: Evaluation of the cyclooxygenase inhibiting effects of six major cannabinoids isolated from Cannabis sativa. PubMed: Cannabinoids act as necrosis-inducing factors in Cannabis sativa. PubMed: Cannabidiolic acid as a selective cyclooxygenase-2 inhibitory component in cannabis. PubMed: Phytocannabinoids in Cannabis sativa: recent studies on biosynthetic enzymes. PubMed: Recent advances in Cannabis sativa research: biosynthetic studies and its potential in biotechnology. PubMed: Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa. PubMed: Growth characteristics of Cannabis sativa L. cultivated in a phytotron and in the field. PubMed: NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa. PubMed: Marijuana extracts possess the effects like the endocrine disrupting chemicals. PubMed: Metabolomic differentiation of Cannabis sativa cultivars using 1H NMR spectroscopy and principal component analysis. PubMed: Membrane associated antitumor effects of crocine-, ginsenoside- and cannabinoid derivates. PubMed: Cannabis 25 (1), biotransformation of cannabidiol and cannabidiolic acid by Pinellia ternata tissue segments. PubMed: Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid. PubMed: Mechanism of action of tricyclic drugs on Escherichia coli and Yersinia enterocolitica plasmid maintenance and replication. PubMed: Cannabinoid acids analysis. PubMed: The effects of cannabinoids and cannabispiro compounds on Escherichia coli adhesion to tissue culture cells and on leukocyte functions in vitro. PubMed: [Isolation of two constituents (cannabidiolic acid and tetrahydrocannabinolic acid) from Cannabis sativa L. by preparative thin layer chromatography]. PubMed: Studies on hashish. 5- Identification of cannabidiol and cannabidiolic acid by ultraviolet spectrophotometry. PubMed: [Hashish. XIX. Ester of cannabidiolic acid and tetrahydrocannabitriol, a new constituent of hashish]. PubMed: Marihuana: Tetrahydrocannabinol and Related Compounds.