Showing Compound Card for BORNYL acetATE (CDB000110)

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Record Information
Version1.0
Created at2020-03-18 23:25:09 UTC
Updated at2020-12-07 19:07:07 UTC
CannabisDB IDCDB000110
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBORNYL acetATE
DescriptionBornyl acetate , also known as isobornyl acetate and pichtosin, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing two fused rings. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Bornyl acetate is the acetylated derivative of borneol. Bornyl acetate is a neutral compound. It is found in spike lavender, coriander, carrot, pine needle, rosemary, sage and valerian root ( Ref:DOI ). Borneol is used in traditional Chinese medicine. It is a component of several plant essential oils and it is considered a natural repellent against the storage insects Liposcelis bostrychophila and Tribolium castaneum (PMID: 30972667 ). Bornyl acetate is also present in trace amount in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl acetic acidGenerator
Isobornyl acetateMeSH
PichtosinMeSH
Chemical FormulaC12H20O2
Average Molecular Weight196.29
Monoisotopic Molecular Weight196.1463
IUPAC Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate
Traditional Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate
CAS Registry Number125-12-2
SMILES
CC(=O)O[C@@H]1C[C@H]2CC[C@]1(C)C2(C)C
InChI Identifier
InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m1/s1
InChI KeyKGEKLUUHTZCSIP-FOGDFJRCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Bornane monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP3.5ALOGPS
logP2.43ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.47 m³·mol⁻¹ChemAxon
Polarizability22.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6dc74fd91a8e34db7f662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-d4d6c0813a5442a8e6842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-5900000000-9e65abc757b4af1cec142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-ab03ff73b57a294a24772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-2900000000-f31d3c48da45d615cb702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe3-3900000000-ed9bf6bb85c9f2090b362016-08-03View 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637531
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. Feng YX, Wang Y, Chen ZY, Guo SS, You CX, Du SS: Efficacy of bornyl acetate and camphene from Valeriana officinalis essential oil against two storage insects. Environ Sci Pollut Res Int. 2019 Jun;26(16):16157-16165. doi: 10.1007/s11356-019-05035-y. Epub 2019 Apr 10. [PubMed:30972667 ]