Record Information
Version1.0
Creation date2010-04-08 22:11:52 UTC
Update date2018-05-28 19:02:46 UTC
Primary IDFDB015493
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameJasmonic acid
DescriptionEsters are present in Jasminum grandiflorum (royal jasmine) and are responsible for its odour [DFC] Jasmonic acid (JA) is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. [Wikipedia]. Jasmonic acid is found in many foods, some of which are soy bean, jerusalem artichoke, common wheat, and japanese pumpkin.
CAS Number59366-47-1
Structure
Thumb
Synonyms
SynonymSource
(-)-Jasmonic acidChEBI
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetic acidChEBI
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetic acidChEBI
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetateChEBI
JasmonateChEBI
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetic acidKegg
(-)-JasmonateKegg
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetateGenerator
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetateGenerator
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetic acidGenerator
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetateGenerator
7-Epi-jasmonic acidHMDB
(1R,2R)-3-oxo-2-(2Z)-2-penten-ylcyclopentanacetic acidbiospider
(1R,2R)-3-oxo-2-(pent-2Z-enyl)-cyclopentaneacetic acidbiospider
3-Oxo-2-(2-pentenyl)cyclopentaneacetic acidbiospider
3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid, 9CI, 8CIdb_source
3-Oxo-2-(2Z-pentenyl)cyclotentylacetic acidbiospider
Jasmonic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP2.36ALOGPS
logP2.41ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.56 m³·mol⁻¹ChemAxon
Polarizability22.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H18O3
IUPAC name2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid
InChI IdentifierInChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
InChI KeyZNJFBWYDHIGLCU-HWKXXFMVSA-N
Isomeric SMILESCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
Average Molecular Weight210.2695
Monoisotopic Molecular Weight210.125594442
Classification
Description belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentJasmonic acids
Alternative Parents
Substituents
  • Jasmonic acid
  • Cyclic ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.55%; H 8.63%; O 22.83%DFC
Melting PointNot Available
Boiling PointBp0.001 125°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -83.5 (c, 0.97 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn19D 1.4885DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gc1-3910000000-fc5414b8972660237107View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-1960000000-15b13e2686e63dbec8acView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fur-5920000000-56a3bfca05d9c2a0fb58View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-6900000000-6dbc88cef2dd120798d4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fy9-9450000000-0d94fd142631685c4b7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1940000000-cbdd7749a0552b6dcb18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-9700000000-4b9efb60332c4d520667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-e7e90e131d7ac7d27a35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0690000000-d03d837380060d855a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3950000000-30695cc3cca6390fcaceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9400000000-c0d8ea2d3164bace07b2View in MoNA
ChemSpider ID4444606
ChEMBL IDNot Available
KEGG Compound IDC08491
Pubchem Compound ID5281166
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32797
CRC / DFC (Dictionary of Food Compounds) IDKCT55-C:KCT55-C
EAFUS IDNot Available
Dr. Duke IDJASMONIC-ACID|(-)-JASMONIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000218
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDJasmonic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
phytohormonal26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).