Methyl jasmonate - ≥95% , CAS No.39924-52-2

CAS: 39924-52-2 Cat. No.: M111207 Molecular Weight: 224.3 EC Number: 254-705-5

GRADE & PURITY ≥95%

Synonyms

FEMA No. 3410 | Methyl jasmonate synthetic a-tocopherol as stabilizer | Methyl2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate | SCHEMBL2496795 | Jasmonic acid methyl ester | Cyclopentaneacetic acid, 3-oxo-2-(2-penten-1-yl)-, methyl ester | HY-W013507 | Met

Storage

Room temperature

Shipped In

Normal

Overview

The jasmonates are a group of plant stress hormones that naturally occur in plants following exposure to particular stresses, including pathogen and herbivore attacks. This compound is a mixture of trans (3R/7R and 3S/7S) isomers and 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. Methyl jasmonate derivatives also have potential as anti-inflammatory agents.
A compound that induces the synthesis of proteinase inhibitors in plant leaves

Specifications

Synonyms

FEMA No. 3410 | Methyl jasmonate synthetic a-tocopherol as stabilizer | Methyl2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate | SCHEMBL2496795 | Jasmonic acid methyl ester | Cyclopentaneacetic acid, 3-oxo-2-(2-penten-1-yl)-, methyl ester | HY-W013507 | Met

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504763765
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763765
• Canonical Smiles: CCC=CCC1C(CCC1=O)CC(=O)OC
• IUPAC Name: methyl 2-[3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetate
• InChIKey: 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+
• Isomeric SMILES: CC/C=C/CC1C(CCC1=O)CC(=O)OC
• WGK Germany: 3
• Alternate CAS: 1101843-02-0；1211-29-6
• Molecular Weight: 224.3
• Reaxy-Rn: 2939212
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2939212&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Lineolic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Lineolic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Jasmonic acids
• Alternative Parents: Methyl esters Cyclic ketones Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Jasmonic acid - Methyl ester - Cyclic ketone - Ketone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol (~30 mg/ml), DMSO (~15 mg/ml), DMF (~25 mg/ml), and PBS pH 7.2 (~3 mg/ml).
• Refractive Index: 1.474
• Flash Point(°F): >235.4 °F
• Flash Point(°C): 113 °C
• Boil Point(°C): 110°C
• Molecular Weight: 224.300 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 224.141 Da
• Monoisotopic Mass: 224.141 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 281.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

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