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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:15:25 UTC
Update Date2022-03-07 02:54:49 UTC
HMDB IDHMDB0036198
Secondary Accession Numbers
  • HMDB36198
Metabolite Identification
Common 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.
Structure
Data?1564520434
Synonyms
ValueSource
(+)-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
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name(2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Traditional Name(2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
CAS Registry Number23178-88-3
SMILES
[H][C@]1(CCC(C)=CC1)[C@](C)(O)CCC=C(C)C
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point314.00 to 315.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.69 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.070 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.18131661259
DarkChem[M-H]-151.14931661259
DeepCCS[M+H]+156.13830932474
DeepCCS[M-H]-153.74230932474
DeepCCS[M-2H]-187.4630932474
DeepCCS[M+Na]+162.2130932474
AllCCS[M+H]+155.932859911
AllCCS[M+H-H2O]+152.232859911
AllCCS[M+NH4]+159.432859911
AllCCS[M+Na]+160.432859911
AllCCS[M-H]-161.832859911
AllCCS[M+Na-2H]-162.632859911
AllCCS[M+HCOO]-163.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-alpha-Bisabolol[H][C@]1(CCC(C)=CC1)[C@](C)(O)CCC=C(C)C2140.4Standard polar33892256
(+)-alpha-Bisabolol[H][C@]1(CCC(C)=CC1)[C@](C)(O)CCC=C(C)C1631.9Standard non polar33892256
(+)-alpha-Bisabolol[H][C@]1(CCC(C)=CC1)[C@](C)(O)CCC=C(C)C1663.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-alpha-Bisabolol,1TMS,isomer #1CC(C)=CCC[C@@](C)(O[Si](C)(C)C)[C@H]1CC=C(C)CC11769.1Semi standard non polar33892256
(+)-alpha-Bisabolol,1TBDMS,isomer #1CC(C)=CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC=C(C)CC12012.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-alpha-Bisabolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-9210000000-7ff1f52ea934fff751092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-alpha-Bisabolol GC-MS (1 TMS) - 70eV, Positivesplash10-004j-9150000000-f0d65214b563c1fe0e8e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-alpha-Bisabolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 10V, Negative-QTOFsplash10-00di-0090000000-dc36029a7670fe05fa752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 20V, Negative-QTOFsplash10-00di-2190000000-aba6002bf895bc6a57622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 40V, Negative-QTOFsplash10-0002-9710000000-0aec4bfc3f14d590d3ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 10V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 20V, Negative-QTOFsplash10-00di-0290000000-4b15d43984c03b619c112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 40V, Negative-QTOFsplash10-0kmi-1940000000-0ccfc6b1df77fb556c032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 10V, Positive-QTOFsplash10-0ab9-1290000000-205c7c190671df2e01412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 20V, Positive-QTOFsplash10-05u2-9730000000-867964dcbacd7531be852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 40V, Positive-QTOFsplash10-0gb9-9400000000-531e5c4b5695ad0e8e092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 10V, Positive-QTOFsplash10-059j-4920000000-a1ba351b509e5f240f4d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 20V, Positive-QTOFsplash10-0a5j-7900000000-1f54ff8424c7d80eebe42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Bisabolol 40V, Positive-QTOFsplash10-0006-9100000000-4ce3d02192df7090cca82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015054
KNApSAcK IDC00003103
Chemspider ID1266723
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549992
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1560811
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.