Geranyl acetate (T3D4837)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 05:18:36 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4837
Identification
Common NameGeranyl acetate
ClassSmall Molecule
DescriptionNeryl acetate is found in cardamom. Neryl acetate is found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Neryl acetate is a flavouring agent. Geranyl acetate belongs to the family of Fatty Alcohol Esters. These are ester derivatives of a fatty alcohol.
Compound Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(2E)-3,7-Dimethyl-2,6-octadienyl acetate
(2E)-3,7-dimethylocta-2,6-dien-1-yl acetate
(E)-3,7-Dimethyl-2,6-octadien-1-yl acetate
(Z)-3,7-Dimethyl-2,6-octadienyl acetate
1,6-Octadiene, 7-methyl-3-methylene-, acetylated
1-Octanol, 3,7-dimethyl-, 1-acetate, tetradehydro deriv.
1-Octanol, 3,7-dimethyl-, acetate, tetradehydro deriv.
2,6-Dimethyl-2,6-octadiene-8-yl acetate
2,6-Octadien-1-ol, 3,7-dimethyl-, acetate
3,7-Dimethyl-1-acetate(2E)-2,6-Octadien-1-ol
3,7-Dimethyl-1-acetate(2Z)-2,6-Octadien-1-ol
3,7-Dimethyl-2,6-octadien-1-ol acetate
3,7-Dimethyl-acetate(2E)-2,6-Octadien-1-ol
3,7-Dimethyl-acetate(2Z)-2,6-Octadien-1-ol
3,7-Dimethyl-acetate(E)-2,6-Octadien-1-ol
3,7-Dimethyl-acetatetrans-2,6-Octadien-1-ol
3,7-Dimethyloctyl acetate, tetradehydro derivative
Acetic acid, geraniol ester
Acetic acid, geranyl ester
cis-3,7-Dimethyl-2,6-octadien-1-ol acetate
cis-3,7-Dimethyl-2,6-octadien-1-yl acetate
cis-3,7-Dimethyl-2,6-octadien-1-yl ethanoate
cis-Geranyl acetate
FEMA 2509
Geranyl acetate a
Geranyl acetic acid
Geranyl ethanoate
Meraneine
Nerol acetate (6CI)
Neryl ethanoate
trans-2,6-Dimethyl-2,6-octadien-8-yl ethanoate
trans-3,7-Dimethyl-2,6-octadien-1-yl acetate
trans-3,7-Dimethyl-2,6-octadien-1-yl ethanoate
trans-3,7-Dimethyl-2,6-octadienyl acetate
Trans-geraniol acetate
Trans-geranyl acetate
Chemical FormulaC12H20O2
Average Molecular Mass196.286 g/mol
Monoisotopic Mass196.146 g/mol
CAS Registry Number105-87-3
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl acetate
Traditional Nameneryl acetate
SMILES[H]\C(COC(C)=O)=C(/C)CCC=C(C)C
InChI IdentifierInChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8-
InChI KeyInChIKey=HIGQPQRQIQDZMP-FLIBITNWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Monoterpenoid
  • Acyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25 °C
Boiling PointNot Available
SolubilityNot Available
LogP4.04
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP4.11ALOGPS
logP2.94ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.33 m³·mol⁻¹ChemAxon
Polarizability23.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-93c6abc7985ec7f0a4882017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ko-9500000000-cdf126f2c6e288b8761f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-867992beb9e7c804a69d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-93c6abc7985ec7f0a4882018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ko-9500000000-cdf126f2c6e288b8761f2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-867992beb9e7c804a69d2018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-014l-9100000000-b15d9b4b6de3799488d02020-07-08View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9400000000-f7513133120d5e44712a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-1900000000-e07e2965d977a6e2825d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-e5f05dabacd073dce84c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9100000000-4932e3e742f871bd93002016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-4900000000-7a2e3b89cdc43f9c61742016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-3c0cda66ebfc365b1b712016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-02983c019224fd67a6c72016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB35157
PubChem Compound ID1549025
ChEMBL IDCHEMBL2268549
ChemSpider ID1266018
KEGG IDC09861
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkGeranyl_acetate
References
Synthesis ReferenceNot Available
MSDST3D4837.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Nuclear receptor subfamily 1 group I member 2
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.617 uMNVS_NR_hPXRNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]