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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 09:35:11 UTC
Update Date2020-02-26 21:24:55 UTC
HMDB IDHMDB0004043
Secondary Accession Numbers
  • HMDB04043
  • HMDB36086
Metabolite Identification
Common Namealpha-Terpineol
Descriptionalpha-Terpineol (CAS: 98-55-5) 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 odour similar to lilac and is a common ingredient in perfumes, cosmetics, and flavours (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 tumour cells. (PMID: 5556886 , 17083732 , 11131302 , 15009716 ).
Structure
Data?1582752295
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-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
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 Number7785-53-7
SMILES
[H][C@]1(CCC(C)=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 KeyWUOACPNHFRMFPN-VIFPVBQESA-N
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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-a6b151ba8e67f64241acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01qi-9620000000-6c96b32bd4033639edd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0540-5900000000-cda96dbf2d059d85a3c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-057l-9000000000-f219b3601875dbade6b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-3e8ebaa4ae0750710d12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-de13f72872a89c9b2a52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9100000000-f6bc053d285b0f1e22f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0b1926cd4fc400a61e84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-b512881ea0d1ea051199Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-90c166242df69d6dee01Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014552
KNApSAcK IDC00029674
Chemspider ID390927
KEGG Compound IDC09902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerpineol
METLIN IDNot Available
PubChem Compound442501
PDB IDNot Available
ChEBI ID300
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15009716 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.