Record Information
Version1.0
Creation date2011-06-01 17:20:07 UTC
Update date2018-05-29 01:52:37 UTC
Primary IDFDB021853
Secondary Accession Numbers
  • FDB014944
Chemical Information
FooDB Nametrans-Geranic acid
DescriptionGeranic acid, also known as 3,7-dimethylocta-2,6-dienoate or geranate, is a member of the class of compounds known as acyclic monoterpenoids. Acyclic monoterpenoids are monoterpenes that do not contain a cycle. Thus, geranic acid is considered to be a fatty acid lipid molecule. Geranic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Geranic acid, or 3,7-dimethyl-2,6-octadienoic acid, is a pheromone used by some organisms. It is a double bond isomer of nerolic acid .
CAS Number4698-08-2
Structure
Thumb
Synonyms
SynonymSource
3,7-Dimethylocta-2,6-dienoateGenerator
3,7-Dimethyl-2,6-octadienoic acidHMDB
Decaprenoic acidHMDB
Geranic acid (6ci)HMDB
Geranoic acidHMDB
(2E)-3,7-Dimethyl-2,6-octadienoic acidmanual
(E)-Geranic acidmanual
2,6-Octadienoic acid, 3,7-dimethyl-, (2E)-manual
Geranic acid adb_source
trans-Geranic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP2.72ALOGPS
logP2.82ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)5.26ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.05 m³·mol⁻¹ChemAxon
Polarizability19.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O2
IUPAC name3,7-dimethylocta-2,6-dienoic acid
InChI IdentifierInChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)
InChI KeyZHYZQXUYZJNEHD-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCCC(C)=CC(O)=O
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
Classification
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionOilDFC
Mass CompositionC 71.39%; H 9.59%; O 19.02%DFC
Melting PointNot Available
Boiling PointBp0.02 85-87°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066u-9300000000-0e5fa74a29642ffbea56View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0600-9510000000-c63599768f78d24aff89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-63a39683f1ee7ae411e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4900000000-69961fd8b0ac30801f92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000000000-5e0e3fc6d4f6195196b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-2ca07626a0a6f2fc98fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-0900000000-f4de03fb18a11ded1779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-5900000000-140a8e79b9546d577420View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJXL36-P:JXL37-Q
EAFUS IDNot Available
Dr. Duke IDTRANS-GERANIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGeranic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).