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71606-07-0

71606-07-0 Structure

71606-07-0 Structure
IdentificationBack Directory
[Name]

13-EPI-12-OXO PDA
[CAS]

71606-07-0
[Synonyms]

13-EPI-12-OXO PDA
3-epi-12-oxo Phytodienoic Acid
13-EPI-12-OXO PHYTODIENOIC ACID
4-OXO-5R-(2Z)-2-PENTENYL-2-CYCLOPENTENE-1S-OCTANOIC ACID
2-Cyclopentene-1-octanoic acid, 4-oxo-5-(2Z)-2-penten-1-yl-, (1S,5R)-
8-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)octanoic acid
[Molecular Formula]

C18H28O3
[MDL Number]

MFCD08062231
[MOL File]

71606-07-0.mol
[Molecular Weight]

292.41
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 20 mg/ml; DMSO: 10 mg/ml; Ethanol: 100 mg/ml; PBS (pH 7.2): 1 mg/ml
[form ]

Liquid
[color ]

Colorless to light yellow
Safety DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)Exclamation Mark (GHS07)
GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319
[Precautionary statements ]

P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Hazard InformationBack Directory
[Description]

13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases.1 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway.2 While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.
[Uses]

9S,13R)-12-Oxo phytodienoic acid is the isomerization of 12-oxo PDA (HY-118828). (9S,13R)-12-Oxo phytodienoic acid is a lipoxygenase metabolite in the leaves of green plants[1].
[Definition]

ChEBI: 9s,13r-12-Oxophytodienoic Acid is a prostanoid.
[References]

1. Crombie, L., and Mistry, K.M. Synthesis of 12-oxophytodienoic acid (12-oxoPDA) and the compounds of its enzymic degradation cascade in plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-jasmonic acid), as their methyl esters Journal of the Chemical Society 1,1981-1991(1991).
2. Hamberg, M., and Gardner, H.W. Oxylipin pathway to jasmonates: Biochemistry and biological significance Biochim. Biophys. Acta 1165(1),1-18(1992).
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