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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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
cis-JasmoneKegg
(Z)-JasmoneHMDB, MeSH
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
JasmoneMeSH, HMDB
(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 RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrumsplash10-03dl-9700000000-626f6beb94dae241c8a7Spectrum
GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrumsplash10-01r6-9600000000-b7842817d55e1ef34cd5Spectrum
GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrumsplash10-03dl-9700000000-626f6beb94dae241c8a7Spectrum
GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrumsplash10-01r6-9600000000-b7842817d55e1ef34cd5Spectrum
Predicted GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4u-6900000000-4ec9a03205a62c5db571Spectrum
Predicted GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-b3455ba1815cd60172a32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7900000000-df4da4ed2a42175313612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-1ad974119b61c19d8fcb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-54214296816474e678192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-9e2bcdc11fb8c55163ab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9800000000-3aa25aca2cc0986b4e112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0900-5900000000-150eb84c8131eaddd8062021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9300000000-4c74719ab790c3d97cb72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-eac87e59851b2c86a2102021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-defd12a7f890bc9459182021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-7005ce6951d5a76167cd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-4900000000-524d8ff912c0d662ad372021-09-24View Spectrum
NMRNot Available
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 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti cariogenic52217 An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Insectiphile24852 A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
TrichomonicideAn agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.DUKE
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.