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Showing Compound (-)-alpha-Bisabolol (FDB015053)

Record Information
Version1.0
Creation date2010-04-08 22:11:37 UTC
Update date2019-11-26 03:11:09 UTC
Primary IDFDB015053
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-alpha-Bisabolol
Description(+)-alpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (+)-alpha-Bisabolol.
CAS Number23089-26-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+)-a-BisabololGenerator
(+)-Α-bisabololGenerator
Bisabolol, (+)-isomerMeSH, HMDB
BisabololMeSH, HMDB
(+)-(1'R,2R)-alpha-BisabololHMDB
(+)-(1'R,2R)-α-BisabololHMDB
(+)-(1’R,2R)-α-BisabololHMDB
(+)-6R,7R-alpha-BisabololHMDB
(+)-6R,7R-α-BisabololHMDB
(+)-alpha-BisabololHMDB
(alphaR,1R)-alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanolHMDB
(αR,1R)-α,4-Dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanolHMDB
alpha-(+)-BisabololHMDB
d-alpha-BisabololHMDB
d-α-BisabololHMDB
α-(+)-BisabololHMDB
(-)-(4S,8S)-alpha-Bisabololmanual
(-)-a-Bisabololdb_source
(-)-alpha-Bisabololbiospider
((-))-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-olbiospider
α-(-)-bisabololbiospider
α-bisabolol (-)-formbiospider
3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaS,1S)-manual
alpha-(-)-BisabololHMDB
alpha-Bisabolol (-)-formHMDB
alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphas,1S)-3-cyclohexene-1-methanolHMDB
Kamillosanbiospider
L-alpha-Bisabololmanual
LevomenolKegg
Levomenol, INNdb_source
Predicted Properties
PropertyValueSource
logP3.91ChemAxon
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.19 m³·mol⁻¹ChemAxon
Polarizability27.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H26O
IUPAC name(2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
InChI IdentifierInChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m0/s1
InChI KeyRGZSQWQPBWRIAQ-LSDHHAIUSA-N
Isomeric SMILES[H][C@]1(CCC(C)=CC1)[C@](C)(O)CCC=C(C)C
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.02%; H 11.78%; O 7.19%DFC
Melting PointNot Available
Boiling PointBp12 153°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -68.4 (c, 1.16 in EtOH)DFC
Spectroscopic UV DataNot Available
Densityd204 0.92DFC
Refractive Indexn20D 1.4936DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-alpha-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-066r-9210000000-7ff1f52ea934fff75109Spectrum
Predicted GC-MS(-)-alpha-Bisabolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-9150000000-f0d65214b563c1fe0e8eSpectrum
Predicted GC-MS(-)-alpha-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1290000000-205c7c190671df2e01412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05u2-9730000000-867964dcbacd7531be852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9400000000-531e5c4b5695ad0e8e092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-dc36029a7670fe05fa752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2190000000-aba6002bf895bc6a57622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9710000000-0aec4bfc3f14d590d3ba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059j-4920000000-a1ba351b509e5f240f4d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5j-7900000000-1f54ff8424c7d80eebe42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-4ce3d02192df7090cca82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-4b15d43984c03b619c112021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmi-1940000000-0ccfc6b1df77fb556c032021-09-22View Spectrum
NMRNot Available
ChemSpider ID390796
ChEMBL IDCHEMBL1096927
KEGG Compound IDC09621
Pubchem Compound ID442343
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36197
CRC / DFC (Dictionary of Food Compounds) IDJXZ00-S:JXZ01-T
EAFUS IDNot Available
Dr. Duke IDLEVONENOL
BIGG IDNot Available
KNApSAcK IDC00011607
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID23089-26-1
GoodScent IDrw1412691
SuperScent IDNot Available
Wikipedia IDBisabolol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herb
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.