Record Information
Version1.0
Creation date2010-04-08 22:11:33 UTC
Update date2018-05-29 01:15:42 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
Synonyms
SynonymSource
(+)-p-Menth-1-en-8-olChEBI
(1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanolChEBI
(R)-alpha-TerpineolChEBI
(+)-alpha-TerpineolKegg
(1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(R)-a,a,4-Trimethylcyclohex-3-ene-1-methanolGenerator
(R)-Α,α,4-trimethylcyclohex-3-ene-1-methanolGenerator
(R)-a-TerpineolGenerator
(R)-Α-terpineolGenerator
(+)-a-TerpineolGenerator
(+)-Α-terpineolGenerator
a-TerpineolGenerator
Α-terpineolGenerator
(6R)-p-Menth-1-en-8-olHMDB
(R)-(+)-alpha-TerpineolHMDB
(R)-2-(4-Methyl-3-cyclohexenyl)isopropanolHMDB
(R)-p-Menth-1-en-8-olHMDB
(S)-(-)-p-Menth-1-en-8-olHMDB
1-alpha-TerpineolHMDB
2-(4-Methyl-3-cyclohexen-1-yl)-2-propanolHMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-olHMDB
2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)HMDB
2-[(1R)-4-Methylcyclohex-3-en-1-yl]propan-2-olHMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolHMDB
alpha-TerpinenolHMDB
alpha-TerpineoleHMDB
alpha-TerpinolHMDB
L-alpha-TerpineolHMDB
Lily OF valleyHMDB
TerpenolHMDB
TerpineolHMDB
Terpineol schlechthinHMDB
DL-alpha-TerpineolHMDB
alpha-Terpineol, sodium saltHMDB
p-Menth-1-en-8-olHMDB
D-alpha-TerpineolHMDB
(S)-a-TerpineolHMDB
(S)-Α-terpineolHMDB
alpha-TerpineolMeSH
(-)-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)-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
p-Menth-1-en-8-ol, (S)-(-)-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.56 g/LALOGPS
logP3.17ALOGPS
logP2.17ChemAxon
logS-2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name2-[(1R)-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
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-a6b151ba8e67f64241acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01qi-9620000000-6c96b32bd4033639edd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0540-5900000000-cda96dbf2d059d85a3c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-057l-9000000000-f219b3601875dbade6b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-3e8ebaa4ae0750710d12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-de13f72872a89c9b2a52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9100000000-f6bc053d285b0f1e22f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0b1926cd4fc400a61e84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-b512881ea0d1ea051199View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-90c166242df69d6dee01View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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.