6894-38-8

Basic information

• Product Name: (-)-JASMONIC ACID
• Synonyms: (-)-JASMONIC ACID;(+-)-jasmonic acid plant cell*culture tested;Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, (1R,2R)-;(1R)-2β-[(Z)-2-Pentenyl]-3-oxocyclopentane-1α-acetic acid;(1R,2R)-2-[(Z)-2-Pentenyl]-3-oxocyclopentane-1-acetic acid
• CAS NO: 6894-38-8
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.27
• EINECS: 213-192-8
• Product Categories: Heterocycles
• Mol File: 6894-38-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 358.1°C at 760 mmHg
• Flash Point: 184.6°C
• Appearance: /liquid
• Density: 1.061g/cm³
• Vapor Pressure: 4.25E-06mmHg at 25°C
• Refractive Index: nD23 1.486
• Storage Temp.: 2-8°C
• Solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.52±0.10(Predicted)
• CAS DataBase Reference: (-)-JASMONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-JASMONIC ACID(6894-38-8)
• EPA Substance Registry System: (-)-JASMONIC ACID(6894-38-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6894-38-8(Hazardous Substances Data)

Usage

Description

(-)-JASMONIC ACID, also known as (-)-trans Jasmonic Acid, is an enantiomer of trans-Jasmonic Acid and a major constituent of essential oil of Jasmine. It is a hormone-like signaling molecule that is widely distributed throughout the plant kingdom and plays a crucial role in defense response pathways against pathogens and insects. Derived from the oxygenation of the octadecanoid α-linolenic acid by the enzyme lipoxygenase, it has a synthetic pathway that includes a cyclization step yielding a cyclopentanone with structural similarity to the prostaglandin class of animal hormones.

Uses

Used in Fragrance Industry:
(-)-JASMONIC ACID is used as a key ingredient in the fragrance industry for its distinct and pleasant aroma. It is a clear, colorless to very light yellow oil that adheres to the surface of the vial, making it an ideal component for creating various fragrances and perfumes.
Used in Plant Defense Mechanisms:
(-)-JASMONIC ACID is used as a signaling molecule in plants to trigger defense response pathways against pathogens and insects. Its role in the biosynthesis of several enzymes located in the chloroplast helps plants to protect themselves from harmful organisms and environmental stressors.
Used in Agricultural Applications:
(-)-JASMONIC ACID can be used in agricultural applications to enhance the natural defense mechanisms of crops, improving their resistance to diseases and pests. By mimicking the plant's own defense signaling, it can help reduce the need for chemical pesticides and promote sustainable farming practices.

InChI:InChI=1/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1

Upstream product

• 130061-57-3 O-<(-)-Jasmonoyl>-(S)-mandelic acid 
• 130061-55-1 O-<(-)-Jasmonoyl>-(R)-mandelic acid 
• 62653-85-4 (+)-7-iso-jasmonic acid succinimide ester 
• 1211-29-6 Methyl jasmonate 
• 95722-42-2 (+)-7-iso-jasmonic acid methyl ester 
• 1211-29-6 methyl jasmonate 
• 909564-98-3 (1R,Z)-[3-oxo-2-(2-pentenyl)cyclopentyl]acetonitrile 
• 909564-97-2 (1R)-[3-oxo-2-(2-pentynyl)cyclopentyl]acetonitrile 
• 909564-89-2 (1R,2R)-[2-(1-naphthalenesulfonyl)-3-oxocyclopentyl]acetonitrile 
• 909564-96-1 (1R)-[2-(1-naphthalenesulfonyl)-3-oxo-2-(2-pentynyl)cyclopentyl]acetonitrile 
• 16400-32-1 1-bromo-pent-2-yne 
• 83648-24-2 (1R,2R)-3-Oxo-2-(2-pentinyl)cyclopentanessigsaeure-methylester 
• 89395-02-8 (-)-methyl (1R,2R)-2-(2-methoxy-2-oxoethyl)-5-oxocyclopentane-1-carboxylate 
• 107171-88-0 (-)-methyl (1S,2R)-2-(2-methoxy-2-oxoethyl)-5-oxo-1-(pent-2-yn-1-yl)cyclopentane-1-carboxylate 

Downstream Products

• 705254-27-9 (+/-)-(1R,2R)-3-hydroxy-2-[(2Z)-2-pentenyl]cyclopentaneacetic acid 
• 32885-78-2 trans-2,3-Di-(carboxymethyl)-cyclopentanon 
• 1211-29-6 Methyl jasmonate 
• 120330-52-1 (+)-6-epi-7-iso-cucurbic acid 
• 146143-02-4 (3R,6S,7R)-cucurbic acid 
• 162830-92-4 C₁₇H₂₆O₅ 
• 151120-27-3 (11SR)-(-)-hydroxyjasmonic acid 
• 573703-57-8 (2R,3R)-3-(2-Hydroxy-ethyl)-2-((Z)-pent-2-enyl)-cyclopentanol 
• 338982-89-1 2-formylmethyl-1-O-tetrahydropyranyl-3-(2-tetrahydropyranyloxyethyl)-cyclopentanol 
• 338982-91-5 2-(3,3-dibromo-2-propenyl)-1-O-tetrahydropyranyl-3-(2-tetrahydropyranyloxyethyl)-cyclopentanol 
• 338982-93-7 2-(4-acetoxy-2-pentynyl)-1-O-tetrahydropyranyl-3-(2-tetrahydropyranyloxyethyl)-cyclopentanol 
• 146143-03-5 7-iso-cucurbic acid methyl ester 
• 120303-56-2 N-<(-)-jasmonoyl>-S-alanine methyl ester 
• 120303-57-3 N-<(-)-jasmonoyl>-S-tyrosine ethyl ester 

Relevant articles and documents

Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen

In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O- acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5- dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R *,2R*,3′S*, 4′R*,5′R*)-4-hydroxymethyl-3,5- dimethyldihydro-2-furanone, (1R*,2R*, 3′S*,4′R*,5′R *,10′R*,12′R*, 13′R*,14′S*) and (1R *,2R*,3′S*, 4′R*,5′R*,10′S *,12′R*,13′R*, 14′S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2- yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5). The structures of 16-O-acetylbotryosphaerilactones A and C were determined by comparison of their spectral data with those of the corresponding acetyl derivatives obtained by acetylation of botryosphaerilactone A. The metabolites isolated, except 4 and 5, were tested at 1 mg/mL on leaves of grapevine cv. Cannonau and cork oak using the leaf puncture assay. They were also tested on detached grapevine leaves at 0.5 mg/mL and tomato cuttings at 0.1 mg/mL. In all phytotoxic assays only jasmonic acid was found to be active. All metabolites were inactive in the zootoxic assay at 50 μg/mL.

Synthesis of novel methyl jasmonate derivatives and evaluation of their biological activity in various cancer cell lines

Warburg hypothesized that the energy consumption of cancer cells is different than the normal cells. When compared to normal conditions, cancer cells do not undergo tricarboxylic acid (TCA) cycle therefore resulting in more lactate in the cells. Glycolysis pathway is a way of cancer cells to provide energy. The first step in glycolysis is the phosphorylation of glucose to glucose-6-phosphate. This reaction is catalyzed by the hexokinase-II enzyme (HK-II) which is known to be overexpressed in tumor cells. The feeding of cancer cells can be prevented by inhibiting the hexokinase-II enzyme in the first step of aerobic glycolysis. In literature, Methyl Jasmonate (MJ) is known as a Hexokinase-II inhibitor since it disposes VDAC and HK-II interaction on mitochondrial membrane. In our study, we aimed to increase the activity by synthesizing the novel MJ analogues with appropriate modifications. Here we report Hexokinase-2 enzyme and cell viability study results in different cancer cells. Based on the three different cancer cell lines we investigated, our novel MJ analogues proved to be more potent than the original molecule. Thus this research may provide more efficacious/novel HK-II inhibitors and may shed light to develop new anti-cancer agents.

In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.