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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 09:35:11 UTC
Update Date2023-02-21 17:16:51 UTC
HMDB IDHMDB0004043
Secondary Accession Numbers
  • HMDB0036086
  • 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. 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
Thumb
Synonyms
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
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 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
Physiological effect
Disposition
Biological locationSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point37.5 °CNot Available
Boiling Point217.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.71 mg/mL at 25 °CNot Available
LogP2.98LI,J & PERDUE,EM (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1508221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References