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Showing Compound (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one (FDB014294)

Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2019-11-26 03:09:47 UTC
Primary IDFDB014294
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
DescriptionOccurs in peppermint oil, green tea and bergamot oranges (Citrus bergamia) Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in many foods, some of which are fig, spearmint, citrus, and sweet orange.
CAS Number488-10-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
cis-JasmoneKegg
(Z)-JasmoneHMDB
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci)HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci)HMDB
3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-oneHMDB
cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneHMDB
JasmoneHMDB
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneMeSH
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8CI)biospider
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9CI)biospider
2-cyclopenten-1-one, 3-methyl-2-[(2Z)-2-pentenyl]-biospider
3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, (Z)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP3.32ALOGPS
logP3.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.9 m³·mol⁻¹ChemAxon
Polarizability19.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H16O
IUPAC name3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
InChI IdentifierInChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
InChI KeyXMLSXPIVAXONDL-PLNGDYQASA-N
Isomeric SMILESCC\C=C/CC1=C(C)CCC1=O
Average Molecular Weight164.2441
Monoisotopic Molecular Weight164.120115134
Classification
Description belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 80.44%; H 9.82%; O 9.74%DFC
Melting PointNot Available
Boiling PointBp12 134-135°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn22D 1.4979DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-6900000000-4ec9a03205a62c5db571JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-b3455ba1815cd60172a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7900000000-df4da4ed2a4217531361JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-1ad974119b61c19d8fcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-54214296816474e67819JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-9e2bcdc11fb8c55163abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9800000000-3aa25aca2cc0986b4e11JSpectraViewer
ChemSpider ID1266012
ChEMBL IDCHEMBL2251602
KEGG Compound IDC08490
Pubchem Compound ID1549018
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35601
CRC / DFC (Dictionary of Food Compounds) IDJPH11-G:JPJ20-S
EAFUS ID1955
Dr. Duke IDJASMONE|CIS-JASMONE
BIGG IDNot Available
KNApSAcK IDC00029353
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1016891
SuperScent ID1549018
Wikipedia IDJasmone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
trichomonicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
jasmine
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
jasmin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
celery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.