Record Information
Version1.0
Creation date2010-04-08 22:14:41 UTC
Update date2020-09-17 15:34:24 UTC
Primary IDFDB019927
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-3-Hexenyl acetate
Description3-Hexenyl acetate also known as 3-Hexen-1-ol-acetate, belongs to the class of organic compounds known as esters. These are carboxylic acid derivatives in which the acid hydrogen atom has been replaced by an alkyl moiety, forming an ester group. 3-Hexenyl acetate is an acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol or (E)-hex-3-en-1-ol, for this reason there are two 3-hexenyl-acetate isomers, trans- and cis-hexenyl-acetate. Cis-3-hexenyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-3-hexenyl acetate is a sweet, apple, and banana tasting compound and it is therefore used as a food additive. Cis-3-hexenyl acetate has been detected, but not quantified in, several different foods such as tamarinds, sunburst squash (pattypan squash), carobs, pepper (C. baccatum), and swedes.
CAS Number3681-71-8
Structure
Thumb
Synonyms
SynonymSource
(Z)-3-Hexen-1-yl acetateChEBI
(Z)-3-Hexenol acetateChEBI
(Z)-3-Hexenyl acetateChEBI
(Z)-Hex-3-enyl acetateChEBI
3Z-Hexenyl acetateChEBI
cis-3-Hexen-1-yl acetateChEBI
cis-3-Hexenyl ethanoateChEBI
(3Z)-Hex-3-en-1-yl acetateKegg
(Z)-3-Hexen-1-yl acetic acidGenerator
(Z)-3-Hexenol acetic acidGenerator
(Z)-3-Hexenyl acetic acidGenerator
(Z)-Hex-3-enyl acetic acidGenerator
3Z-Hexenyl acetic acidGenerator
cis-3-Hexen-1-yl acetic acidGenerator
cis-3-Hexenyl ethanoic acidGenerator
(3Z)-Hex-3-en-1-yl acetic acidGenerator
cis-3-Hexenyl acetic acidGenerator
(3Z)-3-Hexenyl acetateHMDB
(Z)-3-Hexen-1-ol acetateHMDB
(Z)-3-Hexen-1-yl, acetateHMDB
1-Acetate(3Z)-3-hexen-1-olHMDB
3(Z)-Hexenyl acetateHMDB
3-Hexenol acetate, cisHMDB
Acetate(3Z)-3-hexen-1-olHMDB
Acetate(Z)-3-hexen-1-olHMDB
Acetic acid cis-3-hexenyl esterHMDB
cis-3-Hexen-1-ol, acetateHMDB
cis-3-Hexenol acetateHMDB
cis-3-Hexenyl-1-acetateHMDB
cis-Hex-3-enyl acetateHMDB
FEMA 3171HMDB
Hex-3(Z)-enyl acetateHMDB
Z-Hex-3-en-1-yl acetateHMDB
3-HexenylacetateMeSH, HMDB
3-Hexenyl acetateMeSH, HMDB
cis-3-Hexenyl acetateChEBI
(3Z)-Hexen-1-yl acetateHMDB
(Z)-Hex-3-en-1-yl acetateHMDB
3Z-Hexen-1-ol acetateHMDB
cis-3-Hexen-1-ol acetateHMDB
cis-Hex-3-en-1-yl acetateHMDB
(3Z)-hex-3-en-1-yl acetatebiospider
(Z)-3-hexen-1-ol acetatebiospider
(Z)-3-hexenol acetatebiospider
(Z)-3-hexenyl acetatebiospider
3-Hexen-1-ol, 1-acetate, (3Z)-biospider
3-Hexen-1-ol, acetate, (3Z)-biospider
3-Hexen-1-ol, acetate, (Z)-biospider
3-Hexenyl acetate, (Z)-biospider
3-Hexenyl acetate, cis-biospider
3(Z)-hexenyl acetatebiospider
cis-3-hexen-1-yl acetatebiospider
cis-3-Hexenyl ethanoateChEBI
cis-3-Hexenyl ethanoic acidGenerator
cis-3-Hexenyl-1-Acetatebiospider
cis-hex-3-enyl acetatebiospider
Z-hex-3-en-1-yl acetatebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP2.47ALOGPS
logP1.77ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.61 m³·mol⁻¹ChemAxon
Polarizability16.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H14O2
IUPAC name(3Z)-hex-3-en-1-yl acetate
InChI IdentifierInChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4-
InChI KeyNPFVOOAXDOBMCE-PLNGDYQASA-N
Isomeric SMILESCC\C=C/CCOC(C)=O
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
Classification
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.57%; H 9.92%; O 22.50%DFC
Melting PointNot Available
Boiling PointBp12 66°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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-b9d062023fc53ab220c0Spectrum
GC-MScis-3-Hexenyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-92d448bb2099c2ca8a3eSpectrum
GC-MScis-3-Hexenyl acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-92d448bb2099c2ca8a3eSpectrum
Predicted GC-MScis-3-Hexenyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-f0acc67e981853b1d215Spectrum
Predicted GC-MScis-3-Hexenyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4900000000-5520b4c1a8e0f15f98a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9200000000-0c1cce4833b8fb266c60Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36ca2a715407a2dd7680Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7900000000-db796ac26e9c69e96528Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9200000000-289d9b380c452347bbc5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c8bb62799d02cf5f0d9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-9000000000-a56ff074a6b1befb6aa1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-d9067f1965f70e27bba9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-2a8e4bb754618aaff1ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9500000000-24eb76b6258468844355Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-1411093172d173726d27Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID4515742
ChEMBL IDCHEMBL2251454
KEGG Compound IDC19757
Pubchem Compound ID5363388
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40215
CRC / DFC (Dictionary of Food Compounds) IDGPT98-M:MGD85-H
EAFUS ID674
Dr. Duke IDCIS-3-HEXENYL-ACETATE|CIS-3-HEXEN-1-YL-ACETATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID3681-71-8
GoodScent IDrw1001471
SuperScent IDNot Available
Wikipedia IDNot Available
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
Flavours
FlavorCitations
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
banana
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grassy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).