39924-52-2 Usage
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
Different sources of media describe the Uses of 39924-52-2 differently. You can refer to the following data:
1. 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.
2. 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).
Check Digit Verification of cas no
The CAS Registry Mumber 39924-52-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,9,2 and 4 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 39924-52:
(7*3)+(6*9)+(5*9)+(4*2)+(3*4)+(2*5)+(1*2)=152
152 % 10 = 2
So 39924-52-2 is a valid CAS Registry Number.
InChI:InChI=1/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+
39924-52-2Relevant articles and documents
Synthesis of cis-Hedione and methyl jasmonate via cascade Baylis-Hillman reaction and Claisen ortho ester rearrangement
Chapuis, Christian,Buechi, George H.,Wueest, Hans
, p. 3069 - 3088 (2007/10/03)
The exocyclically unsaturated conjugated keto esters 10, obtained via a Claisen ortho ester rearrangement of the allylic hydroxy ketones 9, were either directly hydrogenated or partially isomerized into the endocyclically unsaturated tetrasubstituted didehydrojasmonoid intermediates 14, prior to a more selective hydrogenation with Pd/C in cyclohexane to the disubstituted oxocyclopentaneacetates 15 (Scheme 2). The key intermediates 9 were obtained either by a four-step sequence, including acetal protection/deprotection from enone 1, in the specific case of hydroxy ketone 9a (Scheme 1), or more directly and generally by a Baylis-Hillman reaction from cyclopent-2-en-1-one (16) and the appropriate aldehydes 17 (Scheme 2). The judicious choice of these aldehydes opens versatile modifications for the stereoselective introduction of the partially cis- or epimerized trans-C(2) jasmonoid side chain, while the Baylis-Hillman reaction, catalyzed by chiral [1,1′-binaphthalene]-2, 2′-diols (BINOLs) 19 (Scheme 3), may be efficiently conducted in a one-pot cascade fashion including the ortho ester Claisen rearrangement.
Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one
Hailes, Helen C,Isaac, Ben,Hashim Javaid
, p. 10329 - 10333 (2007/10/03)
A novel and efficient synthesis of both (±)-methyl epijasmonate and (±)-cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one is described. The key step to establish the cis-stereochemistry on the 5-membered ring is an ionic Diels-Alder reaction, which is high yielding and highly regioselective. Subsequent key steps include oxidative cleavage of the six-membered ring, Wittig coupling and for the synthesis of epijasmonate, the haloform reaction.
Stereochemical Control over Three Contiguous Stereogenic Centers in the Intramolecular Ene Reaction of Activated 1,6-Dienes. Application to the Synthesis of (±)-Methyl Cucurbate and (±)-Methyl Epijasmonate
Sarkar, Tarun K.,Ghorai, Binay K.,Nandy, Sandip K.,Mukherjee, Bireswar,Banerji, Asoke
, p. 6006 - 6011 (2007/10/03)
The influence of a protected alcohol group adjacent to the ene or enophile component on diastereoselectivity in both thermal and Lewis acid-catalyzed 5-(3,4) ene reactions of a series of 1,6-dienes 1-7 has been studied. The results indicate that its effect can be considerable, and in one example, with a gem-dimethyl group on the connecting chain and a large silyl protecting group on the hydroxyl, the diastereocontrol was almost perfect, with three stereogenic centers and one double bond geometry set up in one step, e.g., 4 → 10. This new finding was exploited in a synthesis of epijasmonoid natural products, (±)-methyl cucurbate (19) and (±)-methyl epijasmonate (18) starting from aldehyde 24, where the key step was a highly diastereocontrolled 5-(3,4) ene cyclization 23 → 22. 1 Indian Institute of Technology 2 BARC.
