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

Base Information

• Chemical Name: Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester
• CAS No.: 39924-52-2
• Molecular Formula: C13H20O3
• Molecular Weight: 224.3
• Hs Code.: 2918.30
• European Community (EC) Number: 243-497-1,254-705-5
• DSSTox Substance ID: DTXSID501343890
• Wikipedia: Methyl_jasmonate
• Wikidata: Q72492421,Q104253245
• Mol file: 39924-52-2.mol

Synonyms:3-oxo-2-(2-pentenyl)cyclopentaneacetic acid methyl ester;jasmonic acid methyl ester;methyl epijasmonate;methyl jasmonate

Chemical Property of Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester

Chemical Property:

• Appearance/Colour: Clear to pale yellow liquid
• Vapor Pressure: 0.000965mmHg at 25°C
• Refractive Index: 1.470 - 1.476
• Boiling Point: 302.9 °C at 760 mmHg
• Flash Point: 128.6 °C
• PSA: 43.37000
• Density: 1.004 g/cm³
• LogP: 2.50110
• Solubility.: water: soluble340mg/L at 25°C(lit.)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 224.14124450
• Heavy Atom Count: 16
• Complexity: 281

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl jasmonate ≥98%,stabilized,FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-52/53
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CCC=CCC1C(CCC1=O)CC(=O)OC
• 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. Possible application (Flavor): Has many flavor uses including plum, peach, apricot and tutti-frutti.

Technology Process of Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester

There total 157 articles about Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2R*,3S*)-3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanone (29119-47-9,114029-37-7,37435-88-4,82423-75-4,83648-24-2,131063-53-1) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With hydrogen; Lindlar's catalyst; In toluene; at 20 ℃; for 3h;

DOI:10.1016/S0022-328X(01)00890-7

Reference yield: 95.0%

Methyl 6-oxo-2(E)-dodecen-9-ynoate (73205-94-4) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In methanol; for 1h; under 3677.5 Torr; Ambient temperature;

Reference yield: 90.0%

trans-2-(cis-2-pentenyl)-3-<(methoxycarbonyl)(trimethylsilyl)methyl>cyclopentane-1-one (72049-88-8) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With potassium fluoride; In methanol; water; Ambient temperature;

DOI:10.1021/jo01290a006

upstream raw materials:

n-propyltriphenylphosphonium bromide

methyl 2-(2,2-dimethoxyethyl)-3-oxocyclopentaneacetate

2-[2-(benzyloxy)-1-hydroxyethyl]cyclopent-2-en-1-one

cyclopent-2-enone

Downstream raw materials:

jasmonic acid

methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate

methyl jasmonate

(+/-)-tetrahydrodicranenone

Refernces

• 1、 Kerr, William J.,McLaughlin, Mark,Pauson, Peter L.. "Behaviour of monocomplexed 1,4-diynes in the Khand reaction and use of ethylene equivalent techniques in a convenient route to tritium-labelled methyl jasmonate". . p. 118 - 124. Retrieved 2007/10/03.
• 2、 Hailes, Helen C,Isaac, Ben,Hashim Javaid. "Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one". . p. 10329 - 10333. Retrieved 2007/10/03.