Showing Compound Card for beta-Bisabolol (CDB000350)

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Record Information
Version1.0
Created at2020-03-19 00:32:22 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000350
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 ).Beta-bisabolol is one of more than 140 terpenoids found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol
Traditional Name(1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol
CAS Registry Number15352-77-9
SMILES
C[C@@H](CCC=C(C)C)[C@]1(O)CCC(C)=CC1
InChI Identifier
InChI=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
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036111
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014957
KNApSAcK IDC00011606
Chemspider ID30777157
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12300146
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. Brehm-Stecher BF, Johnson EA: Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother. 2003 Oct;47(10):3357-60. doi: 10.1128/aac.47.10.3357-3360.2003. [PubMed:14506058 ]