methyl (Z)-jasmonate

cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-penten-1-yl]-, methyl ester

CAS: 20073-13-6 C13 H20 O3 MW: 224.30000000 floral

Identification

Namemethyl (Z)-jasmonate
IUPACmethyl 2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
CAS Number20073-13-6
EINECS243-497-1
FDA UNIISearch
Molecular FormulaC13 H20 O3
Molecular Weight224.30000000
Nikkaji NumberJ2.354.759G

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 informationMost important hazard(s):
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for methyl (Z)-jasmonate usage levels up tonot for fragrance use.
Recommendation for methyl (Z)-jasmonate flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

FR apple FR apricot FR floral FR gardenia grease FR herbal FR honeysuckle FR jasmin FR lilac FR lily FR melon FR muguet FL pear FR floral FR plum FL tutti frutti

Natural Occurrence

carnation absolute @ <0.01% Data champaca absolute @ 0.20% Data champaca concrete @ 0.06% Data jasmin PMC jasmin absolute concrete egypt @ 0.60% Data jasmin absolute concrete india @ 5.12-7.20% Data jasmin absolute concrete italy @ 3.07% Data neroli oil CO2 extract @ 0.03% Data tea green tea

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.).