Record Information
Version1.0
Creation date2011-05-26 21:25:25 UTC
Update date2018-01-25 19:45:31 UTC
Primary IDFDB021850
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,10-Bisaboladien-7-ol
Description(+)-alpha-bisabolol, also known as bisabolol, (+)-isomer or levomenol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units (+)-alpha-bisabolol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-alpha-bisabolol can be found in german camomile, which makes (+)-alpha-bisabolol a potential biomarker for the consumption of this food product.
CAS Number515-69-5
Structure
Thumb
Synonyms
SynonymSource
((-))-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-olHMDB
(-)-(4S,8S)-alpha-BisabololHMDB
(-)-a-BisabololHMDB
alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphas,1S)-3-cyclohexene-1-methanolHMDB
alpha-(-)-BisabololHMDB
alpha-Bisabolol (-)-formHMDB
KamillosanHMDB
L-alpha-BisabololHMDB
Levomenol, innHMDB
(+)-4-Epi-alpha-bisabololHMDB
Bisabolol, (-)-isomerHMDB
Bisabolol, (+)-isomerHMDB
LevomenolHMDB
BisabololMeSH
(±)-alpha-Bisabololmanual
α-bisabalolmanual
α-bisaboloolmanual
3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaR,1R)-rel-manual
5-Hepten-2-ol, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)- (6CI,7CI,8CI)manual
6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol, 8CIdb_source
6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-olmanual
alpha-Bisabololmanual
Camilolmanual
DL-alpha-Bisabololmanual
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP4.76ALOGPS
logP3.91ChemAxon
logS-3.5ALOGPS
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
Polarizability27.83 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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 PointNot Available
Experimental Water SolubilityNot Available
Experimental logPLog P 4.66 (calc)DFC
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-9210000000-7ff1f52ea934fff75109View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004j-9150000000-f0d65214b563c1fe0e8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1290000000-205c7c190671df2e0141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05u2-9730000000-867964dcbacd7531be85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9400000000-531e5c4b5695ad0e8e09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-dc36029a7670fe05fa75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2190000000-aba6002bf895bc6a5762View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9710000000-0aec4bfc3f14d590d3baView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10586
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJXZ00-S:JXZ00-S
EAFUS ID67
Dr. Duke IDALPHA-BISABOLOL|BISABOLOL
BIGG IDNot Available
KNApSAcK IDC00029679
HET IDNot Available
Flavornet ID515-69-5
GoodScent IDrw1042821
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 / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti burnDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti pepticDUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tuberculic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
candidicideDUKE
cicatrizantDUKE
cosmetic64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
musculotropicDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protisticideDUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spice
  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
flower
  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
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppery
  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).