Terpinyl acetate (YMDB01791)

Identification
YMDB IDYMDB01791
NameTerpinyl acetate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Descriptionalpha-Terpineol acetate, also known as a-terpineol acetic acid or p-menth-1-en-8-yl acetate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on alpha-Terpineol acetate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • |A-terpineol acetate
  • 1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl acetate
  • ACETATE ION
  • acetic acid, ion(1-)
  • alpha-Terpineol acetate
  • alpha-Terpinyl acetate
  • Azetat
  • Ethanoat
  • ethanoate
  • MeCO2 anion
  • p-Menth-1-en-8-ol, acetate
  • p-menth-1-en-8-yl acetate
  • p-Menth-1-en-8-yl acetic acid
  • a-Terpineol acetate
  • a-Terpineol acetic acid
  • alpha-Terpineol acetic acid
  • Α-terpineol acetate
  • Α-terpineol acetic acid
  • FEMA 3047
  • a-Terpinyl acetate
  • a-Terpinyl acetic acid
  • alpha-Terpinyl acetic acid
  • Α-terpinyl acetate
  • Α-terpinyl acetic acid
CAS number80-26-2
WeightAverage: 196.286
Monoisotopic: 196.146329884
InChI KeyIGODOXYLBBXFDW-UHFFFAOYSA-N
InChIInChI=1S/C12H20O2/c1-9-5-7-11(8-6-9)12(3,4)14-10(2)13/h5,11H,6-8H2,1-4H3
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate
Traditional IUPAC Nameα-terpinyl acetate
Chemical FormulaC12H20O2
SMILESCC(=O)OC(C)(C)C1CCC(C)=CC1
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP3.96 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.32ALOGPS
logP2.62ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.61 m³·mol⁻¹ChemAxon
Polarizability23.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-b8293aa3446037e3fc50JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-3882c1dcf928825bf3baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-6900000000-b4a6d18cb758c8c91aa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1010-9300000000-257ef5e703a03c85b0b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-5359896272e433550068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-5a9af9efd8065cc02e7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-7900000000-143c587d14b196b024abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-6900000000-6c4255f51fb20737cf52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001u-9300000000-406d5fb45faab3d92142JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-04361680a71103d6a965JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-94fa9d6a65fb7d565891JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-3900000000-37fb80ce31389d8421e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9500000000-5a05b8a2e1912b54660bJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0032051
Pubchem Compound ID93317
Kegg IDC12300
ChemSpider ID99681
FOODB IDFDB021665
Wikipedia IDNot Available
BioCyc IDNot Available