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Merck

392707

Methyl jasmonate

95%

Synonym(s):

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

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About This Item

Linear Formula:
(O=)C5H6(CH2CH=CHC2H5)CH2CO2CH3
CAS Number:
39924-52-2
Molecular Weight:
224.30
NACRES:
NA.22
PubChem Substance ID:
24864478
UNSPSC Code:
12352100
EC Number:
254-705-5
MDL number:
MFCD00036656
Assay:
95%
Form:
liquid

Key Documents

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InChI key

GEWDNTWNSAZUDX-SNAWJCMRSA-N

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+

SMILES string

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

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

Quality Level

100

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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

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 3 petroleums + Hazardous rank III + Water insoluble liquid

fsl

392707-5ML: + 392707-BULK: + 392707-VAR: + 392707-25ML:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM5421
SHBM5417
SHBL3626
MKCG9069
MKCF2439

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Marco Taurino et al.
SpringerPlus, 4, 49-49 (2015-02-13)
The plant phenol trans-resveratrol, which is mainly found in grape, displays a wide range of biological effects. A cell suspension culture was developed from calli of grape leaves of Vitis vinifera cv. Negramaro in order to study the bioproduction of
Marzena Małgorzata Kurowska et al.
International journal of molecular sciences, 21(12) (2020-06-24)
Jasmonates modulate many growth and developmental processes and act as stress hormones that play an important role in plant tolerance to biotic and abiotic stresses. Therefore, there is a need to identify the genes that are regulated through the jasmonate
Radish sprouts-Characterization and elicitation of novel varieties rich in anthocyanins.
5Baenas N, et al.
Food Research International, 69, 305-312 (2015)
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
E E Farmer et al.
Proceedings of the National Academy of Sciences of the United States of America, 87(19), 7713-7716 (1990-10-01)
Inducible defensive responses in plants are known to be activated locally and systemically by signaling molecules that are produced at sites of pathogen or insect attacks, but only one chemical signal, ethylene, is known to travel through the atmosphere to
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