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
ValueSource
beta-cis-OcimeneChEBI
cis-3,7-Dimethyl-1,3,6-octatrieneChEBI
b-cis-OcimeneGenerator
Β-cis-ocimeneGenerator
cis-β-ocimeneMetaCyc, HMDB
(3Z)-3,7-Dimethyl-1,3,6-octatrieneHMDB
(Z)-3,7-Dimethyl-1,3,6-octatrieneHMDB
(Z)-3,7-Dimethylocta-1,3,6,-trieneHMDB
(Z)-beta-OcimeneHMDB
3,7-Dimethyl-(3Z)-1,3,6-octatrieneHMDB
3,7-Dimethyl-(Z)-1,3,6-octatrieneHMDB
beta -(Z)-OcimeneHMDB
beta -cis-OcimeneHMDB
cis-beta -OcimeneHMDB
cis-beta-OcimeneHMDB
Z-beta -OcimeneHMDB
Z-OcimeneHMDB
(Z)-b-OcimeneGenerator
(Z)-Β-ocimeneGenerator
cis-b-OcimeneGenerator
cis-Β-ocimeneGenerator
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

Route of exposure:

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Biological location:

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
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4900000000-2eaaf884de00c6502b642016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-9400000000-4cc164b437465a5878ea2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-7a6775225dd2fcad42fc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0149d94bf066009726a12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-6c29dab24724f8b32ece2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9600000000-6b5f470455096efc86c32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-83e72aa15e384587ebd82021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-63f5dc5fee3a530dc16f2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-cc6cf03fdb8fe15d9ed02021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-3629c08e44aaa74c273c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-6dbcb07de1e825e783ab2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9000000000-a9f21d2f141933dc84a12021-09-25View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
97 SageDetected and Quantified0.965 mg/g dry wt details
Alien Sour AppleDetected and Quantified0.188 mg/g dry wt details
Black BossDetected and Quantified1.703 mg/g dry wt details
Blue DreamDetected and Quantified0.619 mg/g dry wt details
Blue DreamDetected and Quantified0.847 mg/g dry wt details
Blue DreamDetected and Quantified1.698 mg/g dry wt details
Blue DreamDetected and Quantified1.736 mg/g dry wt details
Bob MarleyDetected and Quantified0.821 mg/g dry wt details
Cosmic LotusDetected and Quantified0.723 mg/g dry wt details
Dairy QueenDetected and Quantified0.312 mg/g dry wt details
Dark Shadow HazeDetected and Quantified1.14 mg/g dry wt details
GabriolaDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
Golden SageDetected and Quantified1.337 mg/g dry wt details
Grape StomperDetected and Quantified0.125 mg/g dry wt details
Grape StomperDetected and Quantified0.132 mg/g dry wt details
Grizzly KushDetected and Quantified1.629 mg/g dry wt details
Hash PlantDetected and Quantified0.052 mg/g dry wt details
Hash PlantDetected and Quantified0.406 mg/g dry wt details
HemlockDetected and Quantified0.969 mg/g dry wt details
Kandy KushDetected and Quantified0.131 mg/g dry wt details
Kush PuppyDetected and Quantified0.053 mg/g dry wt details
La ChocoDetected and Quantified0.545 mg/g dry wt details
Lemon BalmDetected and Quantified0.28 mg/g dry wt details
Lemon GojiDetected and Quantified0.167 mg/g dry wt details
Lemon OGDetected and Quantified0.208 mg/g dry wt details
Lemon SherbetDetected and Quantified1.314 mg/g dry wt details
Lemon SkunkDetected and Quantified0.968 mg/g dry wt details
LohanDetected and Quantified0.384 mg/g dry wt details
Orange SkunkDetected and Quantified0.062 mg/g dry wt details
Pineapple SkunkDetected and Quantified0.109 mg/g dry wt details
Pipe DreamDetected and Quantified0.131 mg/g dry wt details
QuadraDetected and Quantified0.1 mg/g dry wt
    • David S. Wishart,...
 details
Rollex OGDetected and Quantified0.181 mg/g dry wt details
SatoriDetected and Quantified0.154 mg/g dry wt details
Sensi StarDetected and Quantified0.3 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.38 +/- 0.04 mg/g dry wt
    • David S. Wishart,...
 details
Skunk HazeDetected and Quantified0.069 mg/g dry wt details
Skywalker OGDetected and Quantified0.634 mg/g dry wt details
Strawberry FieldsDetected and Quantified1.97 mg/g dry wt details
Strawberry FieldsDetected and Quantified2.027 mg/g dry wt details
Tangerine DreamDetected and Quantified0.274 mg/g dry wt details
Venom OGDetected and Quantified0.235 mg/g dry wt details
White WidowDetected and Quantified1.288 mg/g dry wt details
Wonder WomanDetected and Quantified1.19 mg/g dry wt details
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 ]