Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:11:52 UTC
Update date2018-01-23 19:41:06 UTC
Primary IDFDB015494
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl jasmonate
DescriptionFlavouring ingredient. From Jasminum grandiflorum (royal jasmine) Methyl jasmonate (MeJA) is a substance used in plant defense and also under early research for cancer treatment in humans. Plants produce jasmonic acid and methyl jasmonate in response to many biotic and abiotic stresses (particularly herbivory and wounding), which build up in the damaged parts of the plant. Jasmonates act as signaling compounds for the production of phytoalexins. MeJa has been used to stimulate traumatic resin duct production in lodgepole pine trees. This can be used as a defense against many insect attackers as a type of vaccine. Phytoalexins, once ingested by the attacker (e.g., insect), can be toxic or interfere with its digestion and may deter the attacker from further feeding. The jasmonate signal often spreads systemically throughout the plant and is a major component of systemic acquired resistance. Methyl jasmonate is found in many foods, some of which are adzuki bean, hedge mustard, sourdock, and tinda.
CAS Number1211-29-6
Structure
Thumb
Synonyms
SynonymSource
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl esterChEBI
Methyl (-)-jasmonateChEBI
(-)-Methyl jasmonateKegg
3-oxo-2-(2-Pentenyl)cyclopentaneacetate methyl esterGenerator
Methyl (-)-jasmonic acidGenerator
(-)-Methyl jasmonic acidGenerator
Methyl jasmonic acidGenerator
(-)-Jasmonic acid methyl esterHMDB
(3R,7R)-Methyl jasmonateHMDB
FEMA 3410HMDB
Jasmonic acid methyl esterHMDB
Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetateHMDB
Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetateHMDB
Methyl cis-jasmonateHMDB
Z-Methyl jasmonoateHMDB
Methyl epijasmonateHMDB
3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid methyl esterbiospider
Methyl jasmonatedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.62ALOGPS
logP2.56ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.33 m³·mol⁻¹ChemAxon
Polarizability25.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H20O3
IUPAC namemethyl 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate
InChI IdentifierInChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1
InChI KeyGEWDNTWNSAZUDX-WQMVXFAESA-N
Isomeric SMILESCC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O
Average Molecular Weight224.2961
Monoisotopic Molecular Weight224.141244506
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
  • Methyl ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.61%; H 8.99%; O 21.40%DFC
Melting Point<25 °C
Boiling PointBp0.001 81-84°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -76.5 (c, 3.4 in MeOH)DFC
Spectroscopic UV DataNot Available
Densityd22.6 1.02DFC
Refractive Indexn22D 1.4730DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0036-6900000000-e2a3f1c368618b3e5f44View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aos-6900000000-0277b3467bce13283ff1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1190000000-943fc4cad10af285a2beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-6910000000-b3add72153d54084414bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1950000000-3c4a847eb81b54960c7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05rr-9710000000-500c8cdfcf8ef9dc46d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-6ebb500b1e7a59d8c7e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0490000000-c565f5ccca764f993aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-4980000000-9c08c7091ed7d3a39d47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-8900000000-0e54fbfd7224fd3d6d2fView in MoNA
ChemSpider ID4519204
ChEMBL IDNot Available
KEGG Compound IDC11512
Pubchem Compound ID5367719
Pubchem Substance IDNot Available
ChEBI ID15929
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36583
CRC / DFC (Dictionary of Food Compounds) IDKCT55-C:KCT57-E
EAFUS ID2381
Dr. Duke IDMETHYL-JASMONATE|6-METHYL-JASMONATE| JASMONIC-ACID-METHYL-ESTER
BIGG IDNot Available
KNApSAcK IDC00000219
HET IDNot Available
Flavornet ID1211-29-6
GoodScent IDrw1000141
SuperScent ID5281929
Wikipedia IDMethyl_jasmonate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
jasmine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
melon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
petal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
magnolia
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  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— 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).