Showing Compound Card for (R)-1-Octen-3-ol (CDB000263)

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Record Information
Version1.0
Created at2020-03-19 00:27:39 UTC
Updated at2020-11-18 16:34:58 UTC
CannabisDB IDCDB000263
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(R)-1-Octen-3-ol
Description(R)-1-Octen-3-ol, also known as octenol, 1-vinylhexanol or mushroom alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. (R)-1-Octen-3-ol is a neutral compound. (R)-1-Octen-3-ol is an alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It has been isolated from a few essential oils such as those from lavender, leek, mint and mushrooms. Octenol is named “mushroom alcohol” because is the main flavour component of mushrooms. (R)-1-Octen-3-ol is a naturally occurring organic compound found in several plants including cannabis plants (PMID: 6991645 ). Octenol is formed during the oxidative breakdown of linoleic acid. Octenol attracts biting insects, including mosquitoes. It is believed that some repellents, such as DEET, act by blocking the electrophysiological responses of octenol to the olfactory co-receptor (OR83b or ORCO), an olfactory receptor complex found in highly divergent insect populations (PMID: 18339904 , PMID: 18711137 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-OCTEN-3-olChEBI
Chemical FormulaC8H16O
Average Molecular Weight128.21
Monoisotopic Molecular Weight128.1201
IUPAC Name(3R)-oct-1-en-3-ol
Traditional Name1-octen-3-ol
CAS Registry Number3687-48-7
SMILES
CCCCC[C@@H](O)C=C
InChI Identifier
InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m0/s1
InChI KeyVSMOENVRRABVKN-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.43ALOGPS
logP2.49ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.49ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.17 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-1-Octen-3-ol, 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6992244
PDB IDNot Available
ChEBI ID39932
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. Ditzen M, Pellegrino M, Vosshall LB: Insect odorant receptors are molecular targets of the insect repellent DEET. Science. 2008 Mar 28;319(5871):1838-42. doi: 10.1126/science.1153121. Epub 2008 Mar 13. [PubMed:18339904 ]
  3. Syed Z, Leal WS: Mosquitoes smell and avoid the insect repellent DEET. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13598-603. doi: 10.1073/pnas.0805312105. Epub 2008 Aug 18. [PubMed:18711137 ]