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Identification
YMDB IDYMDB01790
NameTerpinen-4-ol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Descriptionp-Menth-1-en-4-ol, also known as terpinen-4-ol or 1-para-menthen-4-ol, 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. p-Menth-1-en-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 1-Isopropyl-4-methyl-3-cyclohexen-1-ol
  • 1-Methyl-4-isopropyl-1-cyclohexen-4-ol
  • 1-methyl-4-isopropyl-1-cyclohexen-4-ol (4-terpineol)
  • 1-para-Menthen-4-ol
  • 1-Terpinen-4-ol
  • 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-
  • 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)-
  • 3-Cyclohexen-1-ol, 4-methyl-1-[methylethyl]-
  • 4-Carvomenthenol
  • 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
  • 4-Methyl-1-(methylethyl)-3-cyclohexen-1-ol
  • 4-methyl-1-isopropyl-3-cyclohexen-1-ol
  • 4-Terpeneol
  • 4-Terpinenol
  • 4-Terpineol
  • alpha-Terpinen-4-ol
  • I-4-terpineol
  • p-Menth-1-en-4-ol
  • p-Menth-1-en-4-ol, (R)-(-)-
  • para-Menth-1-en-4-ol
  • Terpene-4-ol
  • Terpin-4-en-1-ol
  • Terpin-4-ol
  • Terpine-4-ol
  • Terpinen-4-ol [4S-(+), 4R-(-)]
  • Terpinene-4-ol
  • Terpinenol-4
  • Terpinenolu-4
  • Terpineol-4
  • (+-)-p-Menth-1-en-4-ol
  • 1-Isopropyl-4-methylcyclohex-3-en-1-ol
  • 1-Menthene-4-ol
  • 1-p-Menthen-4-ol
  • Terpinen-4-ol
  • a-Terpinen-4-ol
  • Α-terpinen-4-ol
  • alpha -Terpinen-4-ol
  • FEMA 2248
  • Origanol
  • (R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol
CAS number562-74-3
WeightAverage: 154.2493
Monoisotopic: 154.135765198
InChI KeyWRYLYDPHFGVWKC-UHFFFAOYSA-N
InChIInChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
IUPAC Name4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Traditional IUPAC Nameterpinen-4-ol
Chemical FormulaC10H18O
SMILESCC(C)C1(O)CCC(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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP3.26 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.5 g/LALOGPS
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m³·mol⁻¹ChemAxon
Polarizability18.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
EarthFDB014601
MustFDB014601
MustyFDB014601
NutmegFDB014601
PepperFDB014601
SweetFDB014601
TurpentineFDB014601
WoodyFDB014601
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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 ID78884
HMDB IDHMDB0035833
Pubchem Compound ID11230
Kegg IDC17073
ChemSpider ID10756
FOODB IDFDB014601
Wikipedia IDNot Available
BioCyc IDNot Available