ALPHA-TERPINEOL (CHEM007619)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:28:11 UTC
Update Date2016-11-09 01:13:38 UTC
Accession NumberCHEM007619
Identification
Common NameALPHA-TERPINEOL
ClassSmall Molecule
DescriptionThe (4R)-stereoiosmer of alpha-terpineol.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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, MeSH
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-TerpineolMeSH, HMDB
alpha-Terpineol, sodium saltMeSH, HMDB
P-Menth-1-en-8-olMeSH, HMDB
D-alpha-TerpineolMeSH, HMDB
(S)-a-TerpineolGenerator, HMDB
(S)-Α-terpineolGenerator, HMDB
alpha-TerpineolMeSH
Chemical FormulaC10H18O
Average Molecular Mass154.253 g/mol
Monoisotopic Mass154.136 g/mol
CAS Registry Number98-55-5
IUPAC Name2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional Name(+)-α-terpineol
SMILESCC1=CCC(CC1)C(C)(C)O
InChI IdentifierInChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
InChI KeyWUOACPNHFRMFPN-UHFFFAOYSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-052f-9200000000-ae93728615d3c506a1ceSpectrum
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-118ad26f2b30eb1cab8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9500000000-4ef1ecf90c5038ba6f9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5900000000-4a5f3c6978eb2913079eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-9100000000-e7d43b2d0a8d389277d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c647649541c827cabb3bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004043
FooDB IDFDB014552
Phenol Explorer IDNot Available
KNApSAcK IDC00029674
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerpineol
Chemspider ID390927
ChEBI ID300
PubChem Compound ID442501
Kegg Compound IDC09902
YMDB IDYMDB01373
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4.
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.
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.
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.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
10. The lipid handbook with CD-ROM