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Showing Compound beta-Bisabolol (FDB014957)

Record Information
Version1.0
Creation date2010-04-08 22:11:34 UTC
Update date2020-09-17 15:33:02 UTC
Primary IDFDB014957
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Bisabolol
DescriptionBeta-bisabolol, also known as B-bisabolol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 7640522). However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are two known Bisabolol isomers including Alpha and Beta-bisabolol, which differ in the position of the tertiary alcohol functional group. Beta-bisabolol is a neutral, hydrophobic molecule that is insoluble in water. Beta-bisabolol has a sweet, citrus, floral aroma and a lemon or grapefruit like taste. Industrially, it is used in various fragrances. It has also been used for hundreds of years in cosmetics because of its perceived skin healing properties. Beta-bisabolol is found in a number of plant foods, essential oils and spices including ginger, lemon, black pepper, lavender, and curcumin. Bisabolol has been shown to sensitize pathogenic bacteria to the effects of conventional antibiotics by enhancing the permeability of the bacterial membrane (PMID: 14506058).
CAS Number15352-77-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
b-BisabololGenerator
Β-bisabololGenerator
1-[(1S)-1,5-Dimethyl-4-hexen-1-yl]-4-methyl-(1S)-3-cyclohexen-1-olHMDB
3-Cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl- (8ci)HMDB
beta -BisabololHMDB
β-bisabololbiospider
3-Cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl- (8CI)manual
3-Cyclohexen-1-ol, 1-[(1S)-1,5-dimethyl-4-hexen-1-yl]-4-methyl-, (1S)-manual
beta-Bisabololbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP4.77ALOGPS
logP3.99ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.11 m³·mol⁻¹ChemAxon
Polarizability27.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H26O
IUPAC name(1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol
InChI IdentifierInChI=1S/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3/t14-,15+/m0/s1
InChI KeyWTVHAMTYZJGJLJ-LSDHHAIUSA-N
Isomeric SMILESC[C@@H](CCC=C(C)C)[C@]1(O)CCC(C)=CC1
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
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 PointBp2 121-122°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +23.3 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSbeta-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fr-7910000000-cf7d66a54218a490f801Spectrum
Predicted GC-MSbeta-Bisabolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01u0-9350000000-3a178be52ffc9ddcd73dSpectrum
Predicted GC-MSbeta-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1290000000-120dd0b8763d39b2779b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-7950000000-f18e2e532f1748a717222016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9300000000-5b9184630622fed3fe112016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-db093dd42e3d8c36ca2b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-e9ef85f097bb9ed6fd932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-5910000000-d1c92dab3593b1182e492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3920000000-12d45df2bca136e2ce892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dm-9500000000-6ddd79adfd8968ac3a502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-acd90f238696ae1f83462021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-29715d4df85d92334d152021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9770000000-3905f662f0e341bd18352021-09-23View Spectrum
NMRNot Available
ChemSpider ID30777157
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID27208
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36111
CRC / DFC (Dictionary of Food Compounds) IDJPT26-W:JXM01-G
EAFUS IDNot Available
Dr. Duke IDBETA-BISABOLOL
BIGG IDNot Available
KNApSAcK IDC00011606
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID15352-77-9
GoodScent IDrw1012461
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
sweet
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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
citrus
  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.
tangy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lemon
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  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).