Showing Compound Card for cis-β-ocimene (CDB000297)

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Record Information
Version1.0
Created at2020-03-19 00:29:32 UTC
Updated at2020-12-07 19:07:20 UTC
CannabisDB IDCDB000297
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecis-β-ocimene
DescriptionCis-β-Ocimene or cis-Beta-Ocimene is a naturally occurring organic compound found within a variety of plants and fruits. It is formally classified as an alkatriene although it is biochemically an acyclic monoterpene as it synthesized via multiple isoprene units. Acyclic monoterpens do not contain a cycle. 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-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). There are three known Ocimene isomers including Alpha-, cis-Beta and trans-Beta-Ocimene. Alpha-Ocimene is known as 3,7-dimethyl-1,3,7-octatriene. Beta-Ocimene is known as 3,7-dimethyl-1,3,6-octatriene. Beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. Ocimenes are believed to act as plant defense chemicals and have anti-fungal properties. Cis-β-Ocimene is a neutral, very hydrophobic molecule, practically insoluble in water. It exists as a pale, colorless oil. cis-Beta-Ocimene has a warm, floral, sweet odor and has a spicy, green, metallic taste. It is found naturally in a number of plants and foods including allspice, anise, basil, bay leaf, caraway seed, celery, cinnamon, coriander, dill, fennel, grapefruit, guava, lavender, lemons, limes, mandarin oranges, papaya and parsley. Cis-β-Ocimene is one of more than 140 monoterpenes that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(3Z)-3,7-dimethylocta-1,3,6-triene
Traditional Name(Z)-β-ocimene
CAS Registry Number3338-55-4
SMILES
CC(C)=CC\C=C(\C)C=C
InChI Identifier
InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8-
InChI KeyIHPKGUQCSIINRJ-NTMALXAHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Alkatriene
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

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Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point50 °CWikipedia
Boiling Point100 °C at 70 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.3ALOGPS
logP3.48ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.45 m³·mol⁻¹ChemAxon
Polarizability17.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-787f7f8b1008349f28892015-03-01View Spectrum
GC-MScis-β-ocimene, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-6152f1cd6b53440c9983Spectrum
Predicted GC-MScis-β-ocimene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9200000000-ee73cf7342b73141f4b2Spectrum
Predicted GC-MScis-β-ocimene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
HMDB IDHMDB0030088
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001462
KNApSAcK IDC00000843
Chemspider ID4478390
KEGG Compound IDNot Available
BioCyc IDCPD-4903
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320250
PDB IDNot Available
ChEBI ID87574
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. 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 ]