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Record Information
Version3.6
Creation Date2006-08-13 09:35:11 UTC
Update Date2016-02-11 01:06:32 UTC
HMDB IDHMDB04043
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Terpineol
DescriptionAlpha-Terpineol 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 of terpineol, alpha-, beta-, and gamma-terpineol, with 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. Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors (Wikipedia). alpha-Terpineol is occasionally found as a volatile component in urine. It is a water-soluble component of Melaleuca alternifolia Cheel, the tea tree oil (TTO). alpha-Terpineol is a likely mediator of the in vitro and in vivo activity of the TTO as an agent that could control C. albicans vaginal infections. Purified alpha-Terpineol can suppress pro-inflammatory mediator production by activated human monocytes. alpha-Terpineol is able to impair the growth of human M14 melanoma cells and appear to be more effective on their resistant variants, which express high levels of P-glycoprotein in the plasma membrane, overcoming resistance to caspase-dependent apoptosis exerted by P-glycoprotein-positive tumor cells. (PMID: 5556886 , 17083732 , 11131302 , 15009716 ).
Structure
Thumb
Synonyms
ValueSource
(+)-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-TerpineolHMDB
(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
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolHMDB
alpha-TerpinenolHMDB
alpha-TerpineoleHMDB
alpha-TerpinolHMDB
L-alpha-TerpineolHMDB
Lily OF valleyHMDB
TerpenolHMDB
TerpineolHMDB
Terpineol schlechthinHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional Name(+)-α-terpineol
CAS Registry Number98-55-5
SMILES
CC1=CC[C@@H](CC1)C(C)(C)O
InChI Identifier
InChI=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 KeyInChIKey=WUOACPNHFRMFPN-VIFPVBQESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
  • Used as a flavoring or scent agent
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point37.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 mg/mL at 25 °CNot Available
LogP2.98LI,J & PERDUE,EM (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.56 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.46 m3·mol-1ChemAxon
Polarizability19.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014416
KNApSAcK IDC00029674
Chemspider ID390927
KEGG Compound IDC09902
BioCyc IDCPD-4887
BiGG IDNot Available
Wikipedia Linkalpha-Terpineol
NuGOwiki LinkHMDB04043
Metagene LinkHMDB04043
METLIN IDNot Available
PubChem Compound442501
PDB IDNot Available
ChEBI ID300
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. Mondello F, De Bernardis F, Girolamo A, Cassone A, Salvatore G: In vivo activity of terpinen-4-ol, the main bioactive component of Melaleuca alternifolia Cheel (tea tree) oil against azole-susceptible and -resistant human pathogenic Candida species. BMC Infect Dis. 2006 Nov 3;6:158. [17083732 ]
  3. Hart PH, Brand C, Carson CF, Riley TV, Prager RH, Finlay-Jones JJ: Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes. Inflamm Res. 2000 Nov;49(11):619-26. [11131302 ]
  4. Calcabrini A, Stringaro A, Toccacieli L, Meschini S, Marra M, Colone M, Salvatore G, Mondello F, Arancia G, Molinari A: Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma cells. J Invest Dermatol. 2004 Feb;122(2):349-60. [15009716 ]