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methyl jasmonate

Chemical Structure

General Material Information

Preferred name methyl jasmonate
Trivial Name Methyl 3-oxo-2-(2-penten-1-yl)cyclopentaneacetate
Short Description jasmoneige
Formula C13 H20 O3
CAS Number 39924-52-2
Flavis Number 9.521
ECHA Number 254-705-5
FDA UNII Search
MDL MFCD00151382
COE Number 10821
xLogP3-AA 1.90 (est)
NMR Predictor External link
JECFA Food Flavoring 1400 methyl jasmonate
Synonyms
  • cyclopentaneacetic acid, 3-oxo-2-(2-penten-1-yl)-, methyl ester
  • jasmoneige
  • methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetate
  • methyl [3-oxo-2-(pent-2-en-1-yl)cyclopentyl]acetate
  • methyl 2-(3-oxo-2-pent-2-enylcyclopentyl)acetate
  • methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate
  • methyl 3-oxo-2-(pent-2-enyl) cyclopentane acetate
  • methyl 3-oxo-2-(pent-2-enyl)cyclopentaneacetate
  • methyl 3-oxo-pentenyl cyclopentane acetate
  • methyl 3-oxopentenyl cyclopentane acetate
  • methyl-[3-oxo-2-(pent-2-en-1-yl)cyclopentyl]acetat
  • methyl-3-oxo-2-pent-2-enyl-1-cyclopentylacetate
  • (3-oxo-2-(2-pentenyl)-1-cyclopentyl) acetic acid methyl ester
  • (3-oxo-2-(2-pentenyl)-1-cyclopentyl)acetic acid methyl ester
  • 3-oxo-2-(2-pentenyl)cyclopentaneacetic acid, methyl ester
  • splendione (Firmenich)
  • Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester
  • Methyl 3-oxo-2-(2-penten-1-yl)cyclopentaneacetate
  • Methyl 2-pentenyl-3-oxocyclopentaneacetate

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
methyl 2-(3-oxo-2-pent-2-enylcyclopentyl)acetate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:39924-52-2
Pubchem (cid):62388
Pubchem (sid):135117987
Publications by Info
Methyl Jasmonate
Publications by PubMed
Functional identification of genes responsible for the biosynthesis of 1-methoxy-indol-3-ylmethyl-glucosinolate in Brassica rapa ssp. chinensis.
Identification of potent odorants in Japanese green tea (Sen-cha).
Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible.
Effect of methyl jasmonate on the anthocyanins content and antioxidant activity of blueberries during cold storage.
Aroma changes of black tea prepared from methyl jasmonate treated tea plants.
High mutagenic activity of juice from pak choi (Brassica rapa ssp. chinensis) sprouts due to its content of 1-methoxy-3-indolylmethyl glucosinolate, and its enhancement by elicitation with methyl jasmonate.
Preharvest methyl jasmonate and postharvest UVC treatments: increasing Stilbenes in wine.
Effect of methyl jasmonate, sodium selenate and chitosan as exogenous elicitors on the phenolic compounds profile of broccoli sprouts.
Biotic elicitors effectively increase the glucosinolates content in Brassicaceae sprouts.
THF1 mutations lead to increased basal and wound-induced levels of oxylipins that stimulate anthocyanin biosynthesis via COI1 signaling in Arabidopsis.
Modelling induced resistance to plant diseases.
Postharvest physiology and technology of loquat (Eriobotrya japonica Lindl.) fruit.
Optimization of methyl jasmonate application to broccoli florets to enhance health-promoting phytochemical content.
Foliar abscisic acid content underlies genotypic variation in stomatal responsiveness after growth at high relative air humidity.
Effect of MeJA treatment on polyamine, energy status and anthracnose rot of loquat fruit.
Physicochemical and thermodynamic characterization of the encapsulation of methyl jasmonate by natural and modified cyclodextrins using reversed-phase high-pressure liquid chromatography.
Isolation and expression profiling of GhNAC transcription factor genes in cotton (Gossypium hirsutum L.) during leaf senescence and in response to stresses.
Influence of seasonal variation and methyl jasmonate mediated induction of glucosinolate biosynthesis on quinone reductase activity in broccoli florets.
Cloning and characterization of squalene synthase gene from Poria cocos and its up-regulation by methyl jasmonate.
A systemic response of geophytes is demonstrated by patterns of protein expression and the accumulation of signal molecules in Zantedeschia aethiopica.
Silencing of TaBTF3 gene impairs tolerance to freezing and drought stresses in wheat.
Isolation of the four methyl jasmonate stereoisomers and their effects on selected chiral volatile compounds in red raspberries.
Determination of chiral jasmonates in flowers by GC/MS after monolithic material sorptive extraction.
Antioxidant activity of selected stilbenoids and their bioproduction in hairy root cultures of muscadine grape (Vitis rotundifolia Michx.).
Pre-harvest methyl jasmonate treatment enhances cauliflower chemoprotective attributes without a loss in postharvest quality.
Jasmonate signaling in plant development and defense response to multiple (a)biotic stresses.
Increasing the phenolic compound content of grapes by preharvest application of abcisic acid and a combination of methyl jasmonate and benzothiadiazole.
Accumulation of anthocyanin and associated gene expression in radish sprouts exposed to light and methyl jasmonate.
Elucidating phytochemical production in Juniperus sp.: seasonality and response to stress situations.
The effects of host defence elicitors on betacyanin accumulation in Amaranthus mangostanus seedlings.
Activation of the jasmonic acid plant defence pathway alters the composition of rhizosphere bacterial communities.
Differential expression of calcium/calmodulin-regulated SlSRs in response to abiotic and biotic stresses in tomato fruit.
Buckwheat (Fagopyrum esculentum M.) Sprout Treated with Methyl Jasmonate (MeJA) Improved Anti-Adipogenic Activity Associated with the Oxidative Stress System in 3T3-L1 Adipocytes.
Effect of methyl jasmonate on energy metabolism in peach fruit during chilling stress.
Enhancement of viniferin production in Vitis vinifera L. cv. Alphonse Lavallée Cell suspensions by low-energy ultrasound alone and in combination with methyl jasmonate.
Time of methyl jasmonate application influences the development of 'Cripps Pink' apple fruit colour.
Abiotic induction affects the costs and benefits of inducible herbivore defenses in Datura wrightii.
Postharvest application of methyl jasmonate for improving quality retention of Agaricus bisporus fruit bodies.
Shikimate pathway modulates the elicitor-stimulated accumulation of fragrant 2-hydroxy-4-methoxybenzaldehyde in Hemidesmus indicus roots.
Enhancement of folate content and its stability using food grade elicitors in coriander (Coriandrum sativum L.).
Fragrance material review on methyl jasmonate.
Promoter analyses and transcriptional profiling of eggplant polyphenol oxidase 1 gene (SmePPO1) reveal differential response to exogenous methyl jasmonate and salicylic acid.
Role of pathogen-induced volatiles in the Nicotiana tabacum-Golovinomyces cichoracearum interaction.
Improving grape phenolic content and wine chromatic characteristics through the use of two different elicitors: methyl jasmonate versus benzothiadiazole.
Effect of elicitor spray at different reproductive stages on saponin content of soybean.
Enhanced squalene production by wild-type Saccharomyces cerevisiae strains using safe chemical means.
Methyl jasmonate-induced defense responses are associated with elevation of 1-aminocyclopropane-1-carboxylate oxidase in Lycopersicon esculentum fruit.
Effects of elicitors on the production of resveratrol and viniferins in cell cultures of Vitis vinifera L. cv Italia.
Effect of jasmonates on ethylene biosynthesis and aroma volatile emission in Japanese apricot infected by a pathogen (Colletotrichum gloeosporioides).
Characterization of glycosyltransferases responsible for salidroside biosynthesis in Rhodiola sachalinensis.
Characterization of a single recessive yield trait mutant with elevated endogenous ABA concentration and deformed grains, spikelets and leaves.
Metabolomic analysis of phenolic compounds in buckwheat (Fagopyrum esculentum M.) sprouts treated with methyl jasmonate.
Effect of distillation waste water and plant hormones on spearmint growth and composition.
Enhanced glucosinolates in root exudates of Brassica rapa ssp. rapa mediated by salicylic acid and methyl jasmonate.
Ontogeny and season constrain the production of herbivore-inducible plant volatiles in the field.
(+)-methyl jasmonate-induced bioformation of myricetin, quercetin and kaempferol in red raspberries.
Differential effect of elicitors on biphenyl and dibenzofuran formation in Sorbus aucuparia cell cultures.
Morphological and molecular analyses of host and nonhost interactions involving barley and wheat and the covered smut pathogen Ustilago hordei.
Direct electrochemical determination of methyl jasmonate in wheat spikelet at a nano-montmorillonite film modified electrode by derivative square wave voltammetry.
Effect of methyl jasmonate in combination with ethanol treatment on postharvest decay and antioxidant capacity in Chinese bayberries.
Medicinal mushroom Ganoderma lucidum as a potent elicitor in production of t-resveratrol and t-piceatannol in peanut calluses.
Exogenous methyl jasmonate diminishes the formation of lipid-derived compounds in boiled potato (Solanum tuberosum L.).
Functional characterization of Arabidopsis thaliana WRKY39 in heat stress.
Molecular cloning of a PR-5 like protein gene from cherry tomato and analysis of the response of this gene to abiotic stresses.
Impact of postharvest methyl jasmonate treatment on the volatile composition and flavonol content of strawberries.
Study of the Effect of Methyl Jasmonate Concentration on Aflatoxin B(1) Biosynthesis by Aspergillus parasiticus in Yeast Extract Sucrose Medium.
Methyl jasmonate reduces decay and enhances antioxidant capacity in Chinese bayberries.
Phylogenetic and transcriptional analysis of a strictosidine synthase-like gene family in Arabidopsis thaliana reveals involvement in plant defence responses.
Trypsin inhibitors in passion fruit (Passiflora f. edulis flavicarpa) leaves: accumulation in response to methyl jasmonate, mechanical wounding, and herbivory.
Stress-induced biosynthesis of dicaffeoylquinic acids in globe artichoke.
Overexpression of the apple alcohol acyltransferase gene alters the profile of volatile blends in transgenic tobacco leaves.
Online RPLC-GC via TOTAD method to isolate (+)-methyl epijasmonate from lemon (Citrus limon Burm.).
Priming of antimicrobial phenolics during induced resistance response towards Pectobacterium carotovorum in the ornamental monocot calla lily.
Effect of methyl jasmonate on phenolic compounds and carotenoids of romaine lettuce (Lactuca sativa L.).
Influence of cinnamon and clove essential oils on the D- and z-values of Escherichia coli O157:H7 in apple cider.
Methyl jasmonate and salicylic acid induced oxidative stress and accumulation of phenolics in Panax ginseng bioreactor root suspension cultures.
Resveratrol content in strawberry fruit is affected by preharvest conditions.
[Extraction and identification of volatile constituents in the flowers of Aglaia odorata Lour].
Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota.
Hypericin and hyperforin production in St. John's wort in vitro culture: influence of saccharose, polyethylene glycol, methyl jasmonate, and Agrobacterium tumefaciens.
Chemical changes and overexpressed genes in sweet basil (Ocimum basilicum L.) upon methyl jasmonate treatment.
Chemically induced expression of rice OSB2 under the control of the OsPR1.1 promoter confers increased anthocyanin accumulation in transgenic rice.
Quantification of jasmonic acid by SPME in tomato plants stressed by ozone.
Methyl jasmonate induces defense responses in grapevine and triggers protection against Erysiphe necator.
[Isoflavone accumulation associated with cell structural changes in Maackia amurensis suspension cultures elicited by methyl jasmonate, salicylic acid and nitric oxide].
Novel, unnatural benzo-1,2,3-thiadiazole-7-carboxylate elicitors of taxoid biosynthesis.
Effect of methyl jasmonate on phenolics, isothiocyanate, and metabolic enzymes in radish sprout (Raphanus sativus L.).
Valine pathway is more crucial than phenyl propanoid pathway in regulating capsaicin biosynthesis in Capsicum frutescens mill.
Salicylic acid, ethephon, and methyl jasmonate enhance ester regeneration in 1-MCP-treated apple fruit after long-term cold storage.
Effect of methyl jasmonate on secondary metabolites of sweet basil (Ocimum basilicum L.).
Influence of carrot psyllid (Trioza apicalis) feeding or exogenous limonene or methyl jasmonate treatment on composition of carrot (Daucus carota) leaf essential oil and headspace volatiles.
Parallel synthesis: a new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry.
A wheat xylanase inhibitor gene, Xip-I, but not Taxi-I, is significantly induced by biotic and abiotic signals that trigger plant defense.
Induction of de novo volatile terpene biosynthesis via cytosolic and plastidial pathways by methyl jasmonate in foliage of Vitis vinifera L.
Chemical changes induced by methyl jasmonate in oilseed rape grown in the laboratory and in the field.
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
Stimulated accumulation of lectin mRNA and stress response in Helianthus tuberosus callus by methyl jasmonate.
Wounding stress increases the phenolic content and antioxidant capacity of purple-flesh potatoes (Solanum tuberosum L.).
Imazaquin adsorbed on pillared clay and crystal violet-montmorillonite complexes for reduced leaching in soil.
Novel jasmonate amino acid conjugates in Asparagus officinalis during harvest-induced and natural foliar senescence.
Pathway for the biosynthesis of 4-methyl-1-hexanol volatilized from petal tissue of Nicotiana sylvestris.
Rapid HPLC screening of jasmonate-induced increases in tobacco alkaloids, phenolics, and diterpene glycosides in Nicotiana attenuata.
Methyl jasmonate stimulates aflatoxin B1 biosynthesis by Aspergillus parasiticus.
Improved beta-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate.
Evaluation of volatile chemical treatments for lethality to Salmonella on alfalfa seeds and sprouts.
Olfactory-based discrimination learning in the moth, Manduca sexta.
Purification and characterization of a cystatin from the leaves of methyl jasmonate treated tomato plants.
Fruit-specific lectins from banana and plantain.
Cloning and sequence analysis of cDNA coding for a lectin from Helianthus tuberosus callus and its jasmonate-induced expression.
Efficacy of allyl isothiocyanate in killing enterohemorrhagic Escherichia coli O157:H7 on alfalfa seeds.
Methyl jasmonate reduces chilling injury and maintains postharvest quality of mango fruit.
Identification of potent odorants in Japanese green tea (Sen-cha).
Impact of 1-methylcyclopropene and methyl jasmonate on apple volatile production.
The octadecanoic pathway: signal molecules for the regulation of secondary pathways.
Publications by J-Stage
Effects of Depletion of Glutathione on Abscisic Acid- and Methyl Jasmonate-Induced Stomatal Closure in Arabidopsis thaliana

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
Metabolomics Database:Search
KEGG (GenomeNet):C11512
HMDB (The Human Metabolome Database):HMDB36583
FooDB:FDB015494
Export Tariff Code:2915.39.9500
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 224.30000305176
Specific gravity @ 25 °C
Pounds per Gallon 8.446 to 8.529
Refractive Index 1.47 to 1.476 @ 20 °C
Boiling Point 302 to 303°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.945 est
Solubility
alcohol Yes
water, very slightly Yes
water, 143.5 mg/L @ 25 °C (est) Yes
Stability
APC: 0.5 - 1% Unspecified
candle: 0.5 - 1% Unspecified
detergent: 0.5 - 1% Unspecified
fine fragrances: 0.5 - and up Unspecified
shampoo: 0.5 - 1% Unspecified
shower gel: 0.5 - 1% Unspecified
soap: 0.5 - 1% Unspecified
softener: 0.5 - 1% Unspecified

Organoleptic Properties

Odor Type: Floral
jasmin, floral, oily, green, petal, soft, greasy
Odor strength medium
Substantivity 256 hour(s) at 100.00 %
Luebke, William tgsc, (1988) At 100.00 %. jasmin flower oily green petal soft greasy
Flavor Type: Floral
floral, fruity, magnolia, green, jasmin, oily, kiwi, melon
Luebke, William tgsc, (1988) Floral fruity magnolia green jasmin oily kiwi melon
Floral (jasmine) notes for peach, apricot, grape, and other flavors. Floral, jasmine notes
General comment Floral fruity green waxy seedy melon

Occurrences

Potential Uses

Applications
Odor purposes Apple, Apricot, Floral, Gardenia, Herbal, Honeysuckle, Jasmin, Lilac, Lily, Lily of the valley, Melon, Peach, Pear, Floral, Plum, Valerian
Flavoring purposes Valerian
Other purposes Grease
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for methyl jasmonate usage levels up to:
20.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 26.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.40 (μg/capita/day)
Structure Class: II

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):39924-52-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :62388
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
methyl 2-(3-oxo-2-pent-2-enylcyclopentyl)acetate
Chemidplus:0039924522