12-Oxo-phytodienoic acid

Base Information

• Chemical Name: 12-Oxo-phytodienoic acid
• CAS No.: 85551-10-6
• Molecular Formula: C18H28O3
• Molecular Weight: 292.4131
• DSSTox Substance ID: DTXSID6043705
• Nikkaji Number: J264.010D
• Wikidata: Q27098102
• Metabolomics Workbench ID: 2324
• Mol file: 85551-10-6.mol

Synonyms:12-oxo-cis-10, cis-15-phytodienoic acid;12-oxo-PDA;12-oxo-phytodienoic acid;12-oxophytodienoate;12-oxophytodienoic acid;8-(2-(cis-2'-pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoic acid;OPDA acid

Chemical Property of 12-Oxo-phytodienoic acid

Chemical Property:

• Vapor Pressure: 2.9E-09mmHg at 25°C
• Boiling Point: 447.7°C at 760 mmHg
• Flash Point: 238.7°C
• PSA: 54.37000
• Density: 1.006g/cm³
• LogP: 4.52930
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 292.20384475
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

97% ^*data from raw suppliers

rac12-OxophytodienoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1C(C=CC1=O)CCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C[C@H]1[C@H](C=CC1=O)CCCCCCCC(=O)O
• 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. oarray 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.

Technology Process of 12-Oxo-phytodienoic acid

There total 82 articles about 12-Oxo-phytodienoic acid 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:

13-[S-(Z,E)]-9,11-Hydroperoxyoctadecadienoic acid (18320-18-8) → (9Z,11E)-12-[(1′Z)-hexenyloxy]-9,11-dodecadienoic acid (349491-89-0) + 4-oxo-5α-(2Z)-pentenyl-2-cyclopentene-1α-octanoic acid (85551-10-6) + (ω5Z)-etherolenic acid (169217-39-4,220308-61-2)

Guidance literature:

With HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol; at 20 ℃; for 0.666667h; pH=7.5; Title compound not separated from byproducts.; Enzymatic reaction;

DOI:10.1016/j.phytochem.2008.04.012

Reference yield:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → (9Z,11E)-12-[(1′Z)-hexenyloxy]-9,11-dodecadienoic acid (349491-89-0) + 4-oxo-5α-(2Z)-pentenyl-2-cyclopentene-1α-octanoic acid (85551-10-6) + 13-[S-(Z,E)]-9,11-Hydroperoxyoctadecadienoic acid (18320-18-8) + (ω5Z)-etherolenic acid (169217-39-4,220308-61-2)

Guidance literature:

With HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol; at 20 ℃; for 0.666667h; pH=7.5; Title compound not separated from byproducts.; Enzymatic reaction;

DOI:10.1016/j.phytochem.2008.04.012

Reference yield:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) → cis-(15Z)-12-oxo-10,15-phytodienoic acid (67204-66-4,70630-16-9,71606-07-0,85551-10-6,98673-77-9,111956-15-1,117179-94-9,120199-83-9,134002-16-7)

Guidance literature:

With borate buffer; K-Pi buffer; linseed Me₂CO; In octane; water; at 30 ℃; for 1h; pH 7;

DOI:10.1016/S0031-9422(97)00572-4

upstream raw materials:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

8-[(1S,2S,3aS,4R,7S,7aS)-3-Oxo-2-((Z)-pent-2-enyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-1-yl]-octanoic acid

(15Z)-12-oxo-10,15-phytodienoic acid;

C₄₀H₆₄O₂Si₂

Downstream raw materials:

8-[(1S,2S)-3-Oxo-2-((Z)-pent-2-enyl)-cyclopentyl]-octanoic acid

Refernces

• 1、 Maynard, Daniel,Müller, Sara Mareike,Hahmeier, Monika,L?we, Jana,Feussner, Ivo,Gr?ger, Harald,Viehhauser, Andrea,Dietz, Karl-Josef. "One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid". . p. 1356 - 1364. Retrieved 2018/04/05.
• 2、 Ainai, Takayuki,Matsuumi, Michitaka,Kobayashi, Yuichi. "Efficient total synthesis of 12-oxo-PDA and OPC-8:0". . p. 7825 - 7832. Retrieved 2007/10/03.