Showing Compound Card for Epi-Alpha-Bisabolol (CDB000466)

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Record Information
Version1.0
Created at2020-03-19 00:38:26 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000466
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEpi-Alpha-Bisabolol
DescriptionEpi-Alpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes 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. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) 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. Epi-Alpha-Bisabolol is an isomer of Bisabolol. Bisabolol or more formally α-(−)-bisabolol is a colorless viscous oil. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322 ), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645 , 26657499 ). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569 ). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290). Bisabolol has a weak sweet floral aroma and is used in various fragrances.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-6-Methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-olKegg
(+)-Epi-a-bisabololGenerator
(+)-Epi-α-bisabololGenerator
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Traditional Name(2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
CAS Registry Number515-69-5
SMILES
CC(C)=CCC[C@](C)(O)[C@@H]1CCC(C)=CC1
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-GJZGRUSLSA-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 Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.76ALOGPS
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
Polarizability28.3 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-MSEpi-Alpha-Bisabolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20479
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1201551
PDB IDNot Available
ChEBI ID68658
References
General References
  1. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  2. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  3. Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. [PubMed:22096322 ]
  4. 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 ]
  5. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  6. Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. [PubMed:31659569 ]