CHEBI:67264 - geranic acid

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ChEBI Name geranic acid
ChEBI ID CHEBI:67264
Definition A polyunsaturated fatty acid that is octa-2,6-dienoic acid bearing two methyl substituents at positions 3 and 7 (the 2E-isomer).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H16O2
Net Charge 0
Average Mass 168.23280
Monoisotopic Mass 168.11503
InChI InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+
InChIKey ZHYZQXUYZJNEHD-VQHVLOKHSA-N
SMILES CC(C)=CCC\C(C)=C\C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
pheromone
A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
EC 1.14.18.1 (tyrosinase) inhibitor
Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
Application(s): melanin synthesis inhibitor
A depigmentation agent which inhibits the synthesis of melanin.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing geranic acid (CHEBI:67264) has role antifungal agent (CHEBI:35718)
geranic acid (CHEBI:67264) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
geranic acid (CHEBI:67264) has role melanin synthesis inhibitor (CHEBI:64933)
geranic acid (CHEBI:67264) has role pheromone (CHEBI:26013)
geranic acid (CHEBI:67264) has role plant metabolite (CHEBI:76924)
geranic acid (CHEBI:67264) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
geranic acid (CHEBI:67264) is a methyl-branched fatty acid (CHEBI:62499)
geranic acid (CHEBI:67264) is a monoterpenoid (CHEBI:25409)
geranic acid (CHEBI:67264) is a polyunsaturated fatty acid (CHEBI:26208)
geranic acid (CHEBI:67264) is conjugate acid of geranate (CHEBI:67260)
Incoming geranate (CHEBI:67260) is conjugate base of geranic acid (CHEBI:67264)
IUPAC Name
(2E)-3,7-dimethylocta-2,6-dienoic acid
Synonyms Sources
(E)-3,7-dimethylocta-2,6-dienoic acid ChEBI
3,7-Dimethyl-2E,6-octadienoic acid LIPID MAPS
3,7-Dimethylocta-2,6-dienoate KEGG COMPOUND
Geranilyc acid NIST Chemistry WebBook
Geranoic acid NIST Chemistry WebBook
trans-3,7-dimethyl-2,6-octadien-1-oic acid NIST Chemistry WebBook
trans-geranic acid NIST Chemistry WebBook
trans-geranoic acid NIST Chemistry WebBook
Manual Xrefs Databases
C16461 KEGG COMPOUND
CPD-7618 MetaCyc
Geranic_acid Wikipedia
HMDB0036103 HMDB
LMFA01030784 LIPID MAPS
US2008161397 Patent
US2012014883 Patent
View more database links
Registry Numbers Types Sources
1705144 Reaxys Registry Number Reaxys
459-80-3 CAS Registry Number KEGG COMPOUND
4698-08-2 CAS Registry Number NIST Chemistry WebBook
4698-08-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18081247 PubMed citation Europe PMC
21033696 PubMed citation Europe PMC
21296182 PubMed citation Europe PMC
22286981 PubMed citation Europe PMC
22536331 PubMed citation Europe PMC
23286867 PubMed citation Europe PMC
Last Modified
08 July 2015