8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid CAS#: 85551-10-6

8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid Basic information

Product Name:

8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid

Synonyms:

2-Cyclopentene-1-octanoic acid, 4-oxo-5-(2-pentenyl)-, [1S-[1alpha,5alpha(Z)]]-
2-Cyclopentene-1-octanoic acid, 4-oxo-5-[(2Z)-2-pentenyl]-, (1S,5S)-
Cmc_13962
Cmc_7397
rac 12-Oxophytodienoic Acid
2-Cyclopentene-1-octanoic acid, 4-oxo-5-(2Z)-2-penten-1-yl-, (1S,5S)-
(9S,13S)-12-Oxo-phytodienoic acid
8-[(1S)-4-Oxo-5β-[(Z)-2-pentenyl]-2-cyclopentene-1β-yl]octanoic acid

CAS:

85551-10-6

MF:

C18H28O3

MW:

292.41

Product Categories:

Chiral Reagents
Intermediates & Fine Chemicals
Pharmaceuticals

Mol File:

85551-10-6.mol

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8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid Chemical Properties

Boiling point:: 447.7±24.0 °C(Predicted)
Density: 1.006±0.06 g/cm3(Predicted)
storage temp.: Store at -80°C, protect from light
solubility: DMF: 25 mg/ml; DMSO: 15 mg/ml; Ethanol: 100 mg/ml; PBS pH 7.2: 2 mg/ml
form: Liquid
pka: 4.78±0.10(Predicted)
color: Colorless to light yellow

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8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid Usage And Synthesis

Description

12-oxo Phytodienoic acid (OPDA) is a biologically active, immediate precursor of 7-epi jasmonic acid. In addition to its link with jasmonic acid activity, OPDA appears to play an independent role in mediating resistance to pathogens and pests. As an endogenous signal transducer, OPDA has been shown to increase alkaloid biosynthesis in E. californica cell cultures, increase tendril coiling of B. dioica, and suppress jasmonic acid-induced programmed cell death in a conditional A. flu mutant.

Uses

The octadecanoid 12-oxo-phytodienoic acid (OPDA) is an intermediate in biosynthesis of jasmonic acid in plants. 12-Oxo-phytodienoic acid (OPDA)-induced expression changes in Arabidopsis by cDNA macroarray.

Definition

ChEBI: (15Z)-12-oxophyto-10,15-dienoic acid is a carbocyclic fatty acid, an oxo carboxylic acid and an olefinic fatty acid. It is a conjugate acid of a (15Z)-12-oxophyto-10,15-dienoate.

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