10 G METHYL JASMONATEPURE Chemical Properties

Boiling point:

110 °C/0.2 mmHg(lit.)

Density 

1.02

refractive index 

n20/D 1.474(lit.)

Flash point:

156 °C

storage temp. 

Store at RT

solubility 

water: soluble340mg/L at 25°C(lit.)

form 

Oil

color 

Colourless

Odor

at 100.00 %. jasmin flower oily green petal soft greasy

Odor Type

floral

Merck 

13,5279

InChIKey

GEWDNTWNSAZUDX-PLNGDYQASA-N

LogP

2.945 (est)

EPA Substance Registry System

Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester (39924-52-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-52/53

Safety Statements 

26-61

WGK Germany 

3

10 G METHYL JASMONATEPURE Usage And Synthesis

Description

The jasmonates are a group of plant stress hormones that naturally occur in plants following exposure to certain types of stresses, including pathogen and herbivore attacks. (±)-Jasmonic acid methyl ester is a mixture of trans (3R/7R and 3S/7S) isomers. (±)-Jasmonic acid methyl ester induces the synthesis of proteinase inhibitors in plant leaves. In cancer cells, it suppresses proliferation and induces apoptosis. More specifically, methyl jasmonate inhibits hexokinase that is bound to mitochondria. As hexokinase is overexpressed in cancer cells and contributes to cancer cell growth and survival, methyl jasmonate’s disruption of mitochondrial hexokinase activity selectively targets, and kills, cancer cells. (±)-Jasmonic acid methyl ester derivatives also have potential as anti-inflammatory agents.

Uses

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.

Uses

Possible application (Flavor): Has many flavor uses including plum, peach, apricot and tutti-frutti.

General Description

Methyl jasmonate is a plant growth regulator mainly used to enhance the aroma quality of some fruits and vegetables.

in vitro

it was found that (±)-jasmonic acid methyl ester, when applied to surfaces of tomato plants, could induce the synthesis of defensive proteinase inhibitor proteins. the presence of (±)-jasmonic acid methyl ester in the chamber atmosphere containing plants resulted in the accumulation of proteinase inhibitors in leaves of all studied three species [1]. another study found that (±)-jasmonic acid methyl ester could induce death in each of the studied cell lines, while other plant stress hormones could not affect normal human lymphocytes. in addition, (±)-jasmonic acid methyl ester caused apoptotic death, as measured by flow cytometric dna profile, characteristic nuclear morphology, and caspase-3 activity elevation [2].

in vivo

animal study showed that mice bearing el-4 lymphoma and treated with (±)-jasmonic acid methyl ester survived for significantly longer periods of time than untreated mice, suggesting that plant stress hormones might potentially be a new class of anti-cancer drugs [2].

References

1. farmer, e.e. and ryan, c.a. interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. proceedings of the national academy of sciences of the united states of america 87, 7713-7716 (1990).2. fingrut, o. and flescher, e. plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells. leukemia 16, 608-616 (2002).

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