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Merck

392707

Sigma-Aldrich

Methyl jasmonate

95%

Sinónimos:

3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid, methyl ester, Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate

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About This Item

Fórmula lineal:
(O=)C5H6(CH2CH=CHC2H5)CH2CO2CH3
Número de CAS:
Peso molecular:
224.30
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

liquid

contains

Synthetic α-tocopherol as stabilizer

refractive index

n20/D 1.474 (lit.)

bp

110 °C/0.2 mmHg (lit.)

solubility

water: soluble 340 mg/L at 25 °C(lit.)

density

1.03 g/mL at 25 °C (lit.)

functional group

ester
ketone

SMILES string

CC\C=C\CC1C(CCC1=O)CC(=O)OC

InChI

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+

InChI key

GEWDNTWNSAZUDX-SNAWJCMRSA-N

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General description

Methyl jasmonate (MJ, MeJA), a methyl ester of jasmonic acid (JA) is a plant growth regulator. It is a fragrant volatile compound isolated from the flowers of Jasminum grandiflorum. It has been reported to play an important role in the plant′s response to pathogens and wound.

Application

Methyl jasmonate (MJ, MeJA) is suitable in controlling blue mold decay in sweet cherry fruit caused by Penicillium expansum.

Methyl jasmonate may be used in the following studies:
  • As a potential anti-cancer agent that shows selective cytotoxic effect towards cancer cells.
  • To induce the defensive proteinase inhibitor proteins synthesis in plant leaves.
  • As an elicitor to enrich the total anthocyanin content (TAC) in radish sprouts.
  • As an elicitor in inducing the biosynthesis of trans-resveratrol, a plant phenol in Vitis vinifera cv. Negramaro cell cultures.
  • As a mediator of extensive plant transcriptome reprogramming/ remodeling on exogenous treatment to Salvia sclarea leaves.
  • As a modulator in the expression of chalcone synthase (chs) and proline-rich cell wall protein (PRP), two wound-responsive genes in soybean suspension cultures.
  • As a starting material in the synthesis of [13C,2H3]-MeJA, an internal standard used in the quantitative determination of MeJA in plant tissues.
  • As a test compound in the application of reduced graphene oxide–poly(safranine T) film on glassy carbon electrode (rGO–PST/GCE) in the electrochemical determination of MeJA in jasmine essential oil.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup


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Visite la Librería de documentos

Preparation of Reduced Graphene Oxide-Poly (Safranine T) Film via One-Step Polymerization for Electrochemical Determination of Methyl Jasmonate.
Sun J, et al.
Fullerenes, Nanotubes, and Carbon Nanostructures, 23(8), 701-708 (2015)
Annett Richter et al.
The Plant journal : for cell and molecular biology, 106(1), 245-257 (2021-01-19)
The maize (Zea mays) genome encodes three indole-3-glycerolphosphate synthase enzymes (IGPS1, 2, and 3) catalyzing the conversion of 1-(2-carboxyphenylamino)-l-deoxyribulose-5-phosphate to indole-3-glycerolphosphate. Three further maize enzymes (BX1, benzoxazinoneless 1; TSA, tryptophan synthase alpha subunit; and IGL, indole glycerolphosphate lyase) convert indole-3-glycerolphosphate
Methyl Jasmonate Primed Defense Responses Against Penicillium expansum in Sweet Cherry Fruit.
Wang Lei, et al.
Plant Molecular Biology Reporter, 1-8 (2015)
Yang Yu et al.
Plant biotechnology journal, 18(3), 679-690 (2019-08-17)
Plant defence is multilayered and is essential for surviving in a changing environment. The discovery of long noncoding RNAs (lncRNAs) has dramatically extended our understanding of post-transcriptional gene regulation in diverse biological processes. However, the expression profile and function of
Sharon Cohen et al.
Phytochemistry, 70(13-14), 1600-1609 (2009-08-08)
Jasmonates act as signal transduction intermediates when plants are subjected to environmental stresses such as UV radiation, osmotic shock and heat. In the past few years several groups have reported that jasmonates exhibit anti-cancer activity in vitro and in vivo

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