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Showing Compound (R)-alpha-Terpineol (FDB014552)

Record Information
Version1.0
Creation date2010-04-08 22:11:20 UTC
Update date2020-09-17 15:34:44 UTC
Primary IDFDB014552
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-alpha-Terpineol
Descriptionα-Terpineol, also known as terpineol or p-menth-1-en-8-ol, 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 an isopropyl group at positions 1 and 4 of ring, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are three known terpineol isomers including α, β, and γ-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent. Alpha-Terpineol is a very hydrophobic molecule, practically insoluble in water, but soluble in organic solvents such as methanol, ethanol and ethylacetate. Terpineol has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil.
CAS Number7785-53-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(R)-alpha-Terpineol, non-derivatized, GC-MS Spectrumsplash10-052f-9200000000-ae93728615d3c506a1ceSpectrum
Predicted GC-MS(R)-alpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-a6b151ba8e67f64241acSpectrum
Predicted GC-MS(R)-alpha-Terpineol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01qi-9620000000-6c96b32bd4033639edd2Spectrum
Predicted GC-MS(R)-alpha-Terpineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0540-5900000000-cda96dbf2d059d85a3c52012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-057l-9000000000-f219b3601875dbade6b92012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-3e8ebaa4ae0750710d122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-de13f72872a89c9b2a522017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9100000000-f6bc053d285b0f1e22f42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0b1926cd4fc400a61e842017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-b512881ea0d1ea0511992017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-90c166242df69d6dee012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-118ad26f2b30eb1cab8b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9500000000-4ef1ecf90c5038ba6f9e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5900000000-4a5f3c6978eb2913079e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-9100000000-e7d43b2d0a8d389277d12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c647649541c827cabb3b2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09902
Pubchem Compound ID442501
Pubchem Substance IDNot Available
ChEBI ID300
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJQJ06-Z:JSG43-H
EAFUS IDNot Available
Dr. Duke ID(+)-ALPHA-TERPINEOL|D-ALPHA-TERPINEOL
BIGG IDNot Available
KNApSAcK IDC00010931
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1508221
SuperScent IDNot Available
Wikipedia IDTerpineol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.