Showing Compound Card for (S)-α-Terpineol (CDB005270)

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Record Information
Version1.0
Created at2020-04-17 19:26:22 UTC
Updated at2020-11-18 16:39:38 UTC
CannabisDB IDCDB005270
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(S)-α-Terpineol
Description(S)-alpha-Terpineol, also known as (L)-α-terpineol, 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 (S)-alpha-Terpineol is an extremely weak basic (essentially neutral) compound (based on its pKa). (S)-α-Terpineol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-alpha-TerpineolChEBI
(1S)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(L)-alpha-TerpineolChEBI
(S)-(-)-p-Menth-1-en-8-olChEBI
(S)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(-)-a-TerpineolGenerator
(-)-Α-terpineolGenerator
(1S)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(1S)-Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(L)-a-TerpineolGenerator
(L)-Α-terpineolGenerator
(S)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(S)-Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(S)-a-TerpineolGenerator
(S)-Α-terpineolGenerator
(S)-(-)-a-TerpineolHMDB
(S)-(-)-Α-terpineolHMDB
(S)-alpha-TerpineolChEBI
p-Menth-1-en-8-olMeSH
1-alpha-TerpineolMeSH
alpha-Terpineol, sodium saltMeSH
dl-alpha-TerpineolMeSH
D-alpha-TerpineolMeSH
alpha-TerpineolMeSH
(S)-(-)-TerpineolPhytoBank
(S)-(-)-alpha-TerpineolPhytoBank
l-alpha-TerpineolPhytoBank
l-α-TerpineolPhytoBank
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolPhytoBank
α,α,4-Trimethyl-3-cyclohexene-1-methanolPhytoBank
(±)-alpha-TerpineolPhytoBank
(±)-α-TerpineolPhytoBank
1,1-Dimethyl-1-(4-methylcyclohex-3-enyl)methanolPhytoBank
1-p-Menthen-8-olPhytoBank
2-(4-Methyl-3-cyclohexenyl)-2-propanolPhytoBank
4-(2-Hydroxy-2-propyl)-1-methylcyclohexenePhytoBank
8-Hydroxy-p-menth-1-enePhytoBank
dl-α-TerpineolPhytoBank
α-TerpineolPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional Name(-)-α-terpineol
CAS Registry Number10482-56-1
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-/m1/s1
InChI KeyWUOACPNHFRMFPN-SECBINFHSA-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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability18.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-α-Terpineol, 1 TMS, 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-cda96dbf2d059d85a3c52019-05-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabc2019-05-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-057l-9000000000-f219b3601875dbade6b92019-05-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-b06b43c06bcab8a8b2002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-ecd246742e68c77c01352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-9200000000-7b4cf8729bfcea55f85c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cdc8abcd2a8d0f849b012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-4900000000-28a4ee193904ac2aac652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-24758c06f5cf794027aa2016-08-03View 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Crown OgDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
Fortune CookiesDetected and Quantified0.1 +/- 0.2 mg/g dry wt details
GasDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
GelatoDetected and Quantified0.9 +/- 0.1 mg/g dry wt details
Miami White KushDetected and Quantified0.6 +/- 0.4 mg/g dry wt details
Og KushDetected and Quantified0.5 +/- 0.4 mg/g dry wt details
SherbertDetected and Quantified0.5 +/- 0.4 mg/g dry wt details
Skywalker Og KushDetected and Quantified0.7 +/- 0.4 mg/g dry wt details
Superman Og KushDetected and Quantified0.7 +/- 0.1 mg/g dry wt details
Tahoe Og KushDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
TrainwreckDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Triple ODetected and Quantified0.6 +/- 0.1 mg/g dry wt details
HMDB IDHMDB0036086
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00010932
Chemspider IDNot Available
KEGG Compound IDC11393
BioCyc IDCPD-4887
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443162
PDB IDNot Available
ChEBI ID128
References
General ReferencesNot Available