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

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Name:2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
CAS Number: 1244-58-2Picture of molecule3D/inchi
FDA UNII: FJX8O3OJCD
Nikkaji Web:J14.354E
XlogP3-AA:6.60 (est)
Molecular Weight:358.47790000
Formula:C22 H30 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Cannabidiolic Acid
Coompo
For experimental / research use only.
Cannabidiolic Acid from Plants ≥96%
Odor: characteristic
Use: Cannabidiolic acid inhibits migration of the highly invasive MDA-MB-231 human breast cancer cells, apparently through a mechanism involving inhibition of cAMP-dependent protein kinase A, coupled with an activation of the small GTPase, RhoA. It is established that activation of the RhoA signaling pathway leads to inhibition of the mobility of various cancer cells, including MDA-MB-231 cells. Cannabidiolic acid offers potential therapeutic modality in the abrogation of cancer cell migration, including aggressive breast cancers. Cannabidiolic acid was shown to have a selective inhibitory effect on COX-2. Cannabidiolic acid also prevents nausea-induced behavior in rats by enhancing the activation of the serotonin 5-HT1A receptor.
Sigma-Aldrich
For experimental / research use only.
Cannabidiolic Acid
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for cannabidiolic acid usage levels up to:
 not for fragrance use.
 
Recommendation for cannabidiolic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :160570
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
Chemidplus:0001244582
 
References:
 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):160570
Pubchem (sid):135115684
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10784
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 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
 

Articles:

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.
 
Notes:
None found
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