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Showing Compound (S)-alpha-Terpineol (FDB014922)

Record Information
Version1.0
Creation date2010-04-08 22:11:33 UTC
Update date2019-11-26 03:10:57 UTC
Primary IDFDB014922
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-alpha-Terpineol
DescriptionTerpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (S)-alpha-Terpineol is found in cinnamon, sweet bay, and mentha (mint).
CAS Number10482-56-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-alpha-TerpineolChEBI
1-Menthene-8-olChEBI
1-Methyl-4-isopropyl-1-cyclohexen-8-olChEBI
1-Methyl-4-isopropyl-1-cyclohexene-8-olChEBI
2-(4-Methyl-3-cyclohexenyl)-2-propanolChEBI
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
DL-alpha-TerpineolKegg
1-a-TerpineolGenerator
1-Α-terpineolGenerator
a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
DL-a-TerpineolGenerator
DL-Α-terpineolGenerator
a-TerpineolGenerator
Α-terpineolGenerator
(-)-α-Terpineolbiospider
(-)-a-TerpineolGenerator
(-)-alpha-Terpineolbiospider
(-)-α-terpineolGenerator
(1S)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(1S)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(1S)-α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(L)-a-TerpineolGenerator
(L)-alpha-Terpineolbiospider
(L)-α-terpineolGenerator
(S)-(-)-alpha-Terpineolbiospider
(S)-(-)-p-Menth-1-en-8-olbiospider
(S)-a-TerpineolGenerator
(S)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(S)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(S)-α-terpineolGenerator
(S)-α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (1S)-biospider
3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (S)-biospider
alpha,alpha,4-Trimethyl-(1S)-3-cyclohexene-1-methanolHMDB
alpha,alpha,4-Trimethyl-(S)-3-cyclohexene-1-methanolHMDB
L-α-Terpineolbiospider
L-alpha-Terpineolbiospider
p-Menth-1-en-8-ol, (S)-(-)-biospider
Predicted Properties
PropertyValueSource
logP2.17ChemAxon
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.46 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O
IUPAC name2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
InChI IdentifierInChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1
InChI KeyWUOACPNHFRMFPN-VIFPVBQESA-N
Isomeric SMILESCC1=CC[C@@H](CC1)C(C)(C)O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
Classification
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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting PointMp 37°DFC
Boiling PointBp15 104°DFC
Experimental Water SolubilityNot Available
Experimental logP3.28GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -100.5DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-5e78cee1bf957533902eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-b06b43c06bcab8a8b2002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-ecd246742e68c77c01352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9200000000-7b4cf8729bfcea55f85c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cdc8abcd2a8d0f849b012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-4900000000-28a4ee193904ac2aac652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-24758c06f5cf794027aa2016-08-03View Spectrum
NMRNot Available
ChemSpider ID391434
ChEMBL IDCHEMBL447597
KEGG Compound IDC11393
Pubchem Compound ID443162
Pubchem Substance IDNot Available
ChEBI ID128
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36086
CRC / DFC (Dictionary of Food Compounds) IDJQJ06-Z:JXK12-A
EAFUS IDNot Available
Dr. Duke ID(-)-ALPHA-TERPINEOL
BIGG IDNot Available
KNApSAcK IDC00010932
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1218601
SuperScent IDNot Available
Wikipedia IDTerpineol
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
lilac
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.