methyl (Z)-jasmonate
cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-penten-1-yl]-, methyl ester
Identification
| Name | methyl (Z)-jasmonate |
| IUPAC | methyl 2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate |
| CAS Number | 20073-13-6 |
| EINECS | 243-497-1 |
| FDA UNII | Search |
| Molecular Formula | C13 H20 O3 |
| Molecular Weight | 224.30000000 |
| Nikkaji Number | J2.354.759G |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 299.00 to 302.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.001000 mmHg @ 25.00 °C. (est) |
| Flash Point | 263.00 °F. TCC ( 128.33 °C. ) |
| logP (o/w) | 2.945 (est) |
| Soluble in | water, 143.5 mg/L @ 25 °C (est) |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for methyl (Z)-jasmonate usage levels up to | not for fragrance use. |
| Recommendation for methyl (Z)-jasmonate flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(±)-
cyclopentane acetic acid 3-oxo-trans-2-(cis-2-pentenyl) methyl ester
cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1a,2a(Z)]-
cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-penten-1-yl]-, methyl ester
(-)-
jasmonic acid methyl ester
methyl (-)-jasmonate
methyl (1alpha,2beta(Z))-(1)-3-oxo-2-(pent-2-enyl) cyclopentane acetate
methyl (3-oxo-2-[(2Z)-2-pentenyl]cyclopentyl)acetate
methyl {3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate
methyl 2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
methyl 3-oxo-2-(2Z)-2-pentenyl-(±)-cyclopentane acetic acid methyl ester
methyl cis-jasmonate
(-)-
methyl jasmonate
Info:
Methyl jasmonate
PubMed:
Secondary organic aerosol from aqueous reactions of green leaf volatiles with organic triplet excited States and singlet molecular oxygen.
PubMed:
Habituation in Frankliniella occidentalis to deterrent plant compounds and their blends.
PubMed:
Genome-wide identification and characterization of the Populus WRKY transcription factor family and analysis of their expression in response to biotic and abiotic stresses.
PubMed:
Molecular cloning, expression profiles, and characterization of a novel polyphenol oxidase (PPO) gene in Hevea brasiliensis.
PubMed:
A phenylalanine ammonia-lyase ortholog (PkPAL1) from Picrorhiza kurrooa Royle ex. Benth: molecular cloning, promoter analysis and response to biotic and abiotic elicitors.
PubMed:
Control of foliar pathogens of spring barley using a combination of resistance elicitors.
PubMed:
Genome-wide analysis and identification of stress-responsive genes of the CCCH zinc finger family in Solanum lycopersicum.
PubMed:
Chemical constituents from the linseed meal.
PubMed:
Characterization of mannitol-2-dehydrogenase in Saccharina japonica: evidence for a new polyol-specific long-chain dehydrogenases/reductase.
PubMed:
OsMPK3 is a TEY-type rice MAPK in Group C and phosphorylates OsbHLH65, a transcription factor binding to the E-box element.
PubMed:
Cloning and functional characterization of three branch point oxidosqualene cyclases from Withania somnifera (L.) dunal.
PubMed:
Genome-wide identification and transcriptional profiling analysis of auxin response-related gene families in cucumber.
PubMed:
Behavioural responses of Frankliniella occidentalis Pergande larvae to methyl jasmonate and cis-jasmone.
PubMed:
An inducible NADPH-cytochrome P450 reductase from Picrorhiza kurrooa - an imperative redox partner of cytochrome P450 enzymes.
PubMed:
The dehydrin wzy2 promoter from wheat defines its contribution to stress tolerance.
PubMed:
Studies on the expression of linalool synthase using a promoter-β-glucuronidase fusion in transgenic Artemisia annua.
PubMed:
Studies on the expression of sesquiterpene synthases using promoter-β-glucuronidase fusions in transgenic Artemisia annua L.
PubMed:
Cloning and functional analysis of the promoters that upregulate carotenogenic gene expression during flower development in Gentiana lutea.
PubMed:
Cyclopentanoids from cyclopentadiene: synthesis of (-)-methyl jasmonate and (+)-12-oxophytodienoic acid.
PubMed:
Promoter analysis reveals cis-regulatory motifs associated with the expression of the WRKY transcription factor CrWRKY1 in Catharanthus roseus.
PubMed:
Molecular cloning and expression analysis of PDR1-like gene in ginseng subjected to salt and cold stresses or hormonal treatment.
PubMed:
A receptor-like kinase gene (GbRLK) from Gossypium barbadense enhances salinity and drought-stress tolerance in Arabidopsis.
PubMed:
Reproductive organ and vascular specific promoter of the rice plasma membrane Ca2+ATPase mediates environmental stress responses in plants.
PubMed:
AaERF1 positively regulates the resistance to Botrytis cinerea in Artemisia annua.
PubMed:
Identification of a novel jasmonate-responsive element in the AtJMT promoter and its binding protein for AtJMT repression.
PubMed:
Bacterial pathogen phytosensing in transgenic tobacco and Arabidopsis plants.
PubMed:
Molecular characterization and expression of three galactinol synthase genes that confer stress tolerance in Salvia miltiorrhiza.
PubMed:
GhWRKY15, a member of the WRKY transcription factor family identified from cotton (Gossypium hirsutum L.), is involved in disease resistance and plant development.
PubMed:
Identification of the dehydrin gene family from grapevine species and analysis of their responsiveness to various forms of abiotic and biotic stress.
PubMed:
Functional analysis of a WRKY transcription factor involved in transcriptional activation of the DBAT gene in Taxus chinensis.
PubMed:
Oxylipin Signaling: A Distinct Role for the Jasmonic Acid Precursor cis-(+)-12-Oxo-Phytodienoic Acid (cis-OPDA).
PubMed:
Cloning and molecular characterization of a putative bZIP transcription factor VvbZIP23 from Vitis vinifera.
PubMed:
Molecular cloning, bacterial expression and promoter analysis of squalene synthase from Withania somnifera (L.) Dunal.
PubMed:
Promoter analyses and transcriptional profiling of eggplant polyphenol oxidase 1 gene (SmePPO1) reveal differential response to exogenous methyl jasmonate and salicylic acid.
PubMed:
Molecular cloning and characterization of the promoter of SmGGPPs and its expression pattern in Salvia miltiorrhiza.
PubMed:
Molecular cloning and functional characterization of Catharanthus roseus hydroxymethylbutenyl 4-diphosphate synthase gene promoter from the methyl erythritol phosphate pathway.
PubMed:
The expression pattern of the Picea glauca Defensin 1 promoter is maintained in Arabidopsis thaliana, indicating the conservation of signalling pathways between angiosperms and gymnosperms.
PubMed:
Characterization of the tomato prosystemin promoter: organ-specific expression, hormone specificity and methyl jasmonate responsiveness by deletion analysis in transgenic tobacco plants.
PubMed:
Cloning two P5CS genes from bioenergy sorghum and their expression profiles under abiotic stresses and MeJA treatment.
PubMed:
Predication of Japanese green tea (Sen-cha) ranking by volatile profiling using gas chromatography mass spectrometry and multivariate analysis.
PubMed:
Three Brassica rapa metallothionein genes are differentially regulated under various stress conditions.
PubMed:
Host resistance elicited by methyl jasmonate reduces emission of aggregation pheromones by the spruce bark beetle, Ips typographus.
PubMed:
Common and unique elements of the ABA-regulated transcriptome of Arabidopsis guard cells.
PubMed:
MYC genes with differential responses to tapping, mechanical wounding, ethrel and methyl jasmonate in laticifers of rubber tree (Hevea brasiliensis Muell. Arg.).
PubMed:
Involvement of endogenous abscisic acid in methyl jasmonate-induced stomatal closure in Arabidopsis.
PubMed:
Molecular cloning and characterization of a membrane associated NAC family gene, SiNAC from foxtail millet [Setaria italica (L.) P. Beauv].
PubMed:
Cloning and characterization of a novel stress-responsive WRKY transcription factor gene (MusaWRKY71) from Musa spp. cv. Karibale Monthan (ABB group) using transformed banana cells.
PubMed:
Stilbene production in cell cultures of Vitis vinifera L. cvs Red Globe and Michele Palieri elicited by methyl jasmonate.
PubMed:
Overproduction of alkaloid phytoalexins in California poppy cells is associated with the co-expression of biosynthetic and stress-protective enzymes.
PubMed:
The transcriptome of cis-jasmone-induced resistance in Arabidopsis thaliana and its role in indirect defence.
PubMed:
Isolation of a novel RNA-dependent RNA polymerase 6 from Nicotiana glutinosa, NgRDR6, and analysis of its response to biotic and abiotic stresses.
PubMed:
Methyl jasmonate- or gibberellins A3-induced astaxanthin accumulation is associated with up-regulation of transcription of beta-carotene ketolase genes (bkts) in microalga Haematococcus pluvialis.
PubMed:
GhWRKY3, a novel cotton (Gossypium hirsutum L.) WRKY gene, is involved in diverse stress responses.
PubMed:
Functional identification and regulation of the PtDrl02 gene promoter from triploid white poplar.
PubMed:
Isolation and characterization of AaWRKY1, an Artemisia annua transcription factor that regulates the amorpha-4,11-diene synthase gene, a key gene of artemisinin biosynthesis.
PubMed:
Qualitative variability of lima bean's VOC bouquets and its putative ecological consequences.
PubMed:
Polymorphism in jasmonate signaling partially accounts for the variety of volatiles produced by Nicotiana attenuata plants in a native population.
PubMed:
Molecular cloning and characterization of the promoter for the multiple stress-inducible gene BjCHI1 from Brassica juncea.
PubMed:
NgRDR1, an RNA-dependent RNA polymerase isolated from Nicotiana glutinosa, was involved in biotic and abiotic stresses.
PubMed:
Herbivore-induced volatiles in the perennial shrub, Vaccinium corymbosum, and their role in inter-branch signaling.
PubMed:
The promoter of the pepper pathogen-induced membrane protein gene CaPIMP1 mediates environmental stress responses in plants.
PubMed:
Delayed cytotoxic effects of methyl jasmonate and cis-jasmone induced apoptosis in prostate cancer cells.
PubMed:
Methyl jasmonate decreases membrane fluidity and induces apoptosis through tumor necrosis factor receptor 1 in breast cancer cells.
PubMed:
Natural jasmonates of different structures suppress the growth of human neuroblastoma cell line SH-SY5Y and its mechanisms.
PubMed:
Molecular cloning and characterization of the yew gene encoding squalene synthase from Taxus cuspidata.
PubMed:
Resveratrol content in strawberry fruit is affected by preharvest conditions.
PubMed:
The promoter of the TLC1.1 retrotransposon from Solanum chilense is activated by multiple stress-related signaling molecules.
PubMed:
Jasmonates induce apoptosis and cell cycle arrest in non-small cell lung cancer lines.
PubMed:
Analysis of oxidative signalling induced by ozone in Arabidopsis thaliana.
PubMed:
Isolation and characterization of the first putative peroxidase gene from oilseed rape (Brassica napus) which is highly homologous to HRPC.
PubMed:
Isolation and characterization of OsGSTL1 promoter from rice.
PubMed:
Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores.
PubMed:
Identification and deletion analysis of the promoter of the pepper SAR8.2 gene activated by bacterial infection and abiotic stresses.
PubMed:
Identification of phenylpropanoids in methyl jasmonate treated Brassica rapa leaves using two-dimensional nuclear magnetic resonance spectroscopy.
PubMed:
Cloning, functional expression, and characterization of CYP709C1, the first sub-terminal hydroxylase of long chain fatty acid in plants. Induction by chemicals and methyl jasmonate.
PubMed:
Colonization of the Arabidopsis rhizosphere by fluorescent Pseudomonas spp. activates a root-specific, ethylene-responsive PR-5 gene in the vascular bundle.
PubMed:
Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects.
PubMed:
Jasmonates and Na-orthovanadate promote resveratrol production in Vitis vinifera cv. Barbera cell cultures.
PubMed:
Plant-plant signaling: application of trans- or cis-methyl jasmonate equivalent to sagebrush releases does not elicit direct defenses in native tobacco.
PubMed:
Overexpression of the AP2/EREBP transcription factor OPBP1 enhances disease resistance and salt tolerance in tobacco.
PubMed:
Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. By-2 cell cultures.
PubMed:
Fragrances in oolong tea that enhance the response of GABAA receptors.
PubMed:
The ethylene-, jasmonate-, abscisic acid- and NaCl-responsive tomato transcription factor JERF1 modulates expression of GCC box-containing genes and salt tolerance in tobacco.
PubMed:
Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata.
PubMed:
Methyl jasmonate and cis-jasmone do not dispose of the herbivore-induced jasmonate burst in Nicotiana attenuata.
PubMed:
Epoxide hydrolase: a mRNA induced by the fungal pathogen Alternaria alternata on rough lemon (Citrus jambhiri Lush).
PubMed:
Characterization of a hydroperoxide lyase gene and effect of C6-volatiles on expression of genes of the oxylipin metabolism in Citrus.
PubMed:
Metabolism of deuterium-labeled jasmonic acid and OPC 8:0 in the potato plant (Solanum tuberosum L.).
PubMed:
Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes.
PubMed:
Methyl jasmonate as an allelopathic agent: sagebrush inhibits germination of a neighboring tobacco, Nicotiana attenuata.
PubMed:
Brassica napus soluble epoxide hydrolase (BNSEH1).
PubMed:
A calmodulin-binding/CGCG box DNA-binding protein family involved in multiple signaling pathways in plants.
PubMed:
Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures.
PubMed:
New roles for cis-jasmone as an insect semiochemical and in plant defense.
PubMed:
A 13-bp cis-regulatory element in the LTR promoter of the tobacco retrotransposon Tto1 is involved in responsiveness to tissue culture, wounding, methyl jasmonate and fungal elicitors.
PubMed:
C6-volatiles derived from the lipoxygenase pathway induce a subset of defense-related genes.
PubMed:
A 42 bp fragment of the pmas1' promoter containing an ocs-like element confers a developmental, wound- and chemically inducible expression pattern.
PubMed:
Allene oxide synthase: a major control point in Arabidopsis thaliana octadecanoid signalling.
PubMed:
The untranslated leader sequence of the barley lipoxygenase 1 (Lox1) gene confers embryo-specific expression.
PubMed:
Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible.
PubMed:
Transcriptional activation of the tobacco retrotransposon Tto1 by wounding and methyl jasmonate.
PubMed:
Regulation of sesquiterpene cyclase gene expression. Characterization of an elicitor- and pathogen-inducible promoter.
PubMed:
A peroxidase gene promoter induced by phytopathogens and methyl jasmonate in transgenic plants.
PubMed:
Analysis of 12-oxo-phytodienoic acid enantiomers in biological samples by capillary gas chromatography-mass spectrometry using cyclodextrin stationary phases.
PubMed:
Developmental regulation of two tomato lipoxygenase promoters in transgenic tobacco and tomato.
PubMed:
Coordinated activation of as-1-type elements and a tobacco glutathione S-transferase gene by auxins, salicylic acid, methyl-jasmonate and hydrogen peroxide.
PubMed:
Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures.
PubMed:
Expression of an amino acid biosynthesis gene in tomato flowers: developmental upregulation and MeJa response are parenchyma-specific and mutually compatible.
PubMed:
The octadecanoic pathway: signal molecules for the regulation of secondary pathways.
PubMed:
Identification of G-Box Sequence as an Essential Element for Methyl Jasmonate Response of Potato Proteinase Inhibitor II Promoter.
PubMed:
Isolation and Identification of a Senescence-promoting Substance from Wormwood (Artemisia absinthium L.).