Basic information
- CAS
85551-10-6- Standard SMILES
CC/C=C\C[C@@H]1C(=O)C=C[C@@H]1CCCCCCCC(=O)O- InChIKey
PMTMAFAPLCGXGK-JMTMCXQRSA-N- Molecular formula
- C18H28O3
- Average molar mass
- 292.4 g/mol
- Monoisotopic mass
- 292.20384476
Overview
(15Z)-12-oxophyto-10,15-dienoic acid is an oxo carboxylic acid, a carbocyclic fatty acid and an olefinic fatty acid. It is a conjugate acid of a (15Z)-12-oxophyto-10,15-dienoate.
Names & identifiers
- Preferred name
- 12-Oxo-phytodienoic acid
- IUPAC
- 8-[(1S,5S)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acid
- English name
- 8-[(3S,4S)-4α-[(Z)-2-Pentenyl]-5-oxo-1-cyclopentene-3α-yl]octanoic acid
- Molecular formula
- C18H28O3
- Molecular weight
- 292.41
Names & synonyms
12-Oxo-phytodienoic acid85551-10-68-[(1S,5S)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acidDTXSID60437058-((1S,5S)-4-oxo-5-((Z)-pent-2-enyl)cyclopent-2-en-1-yl)octanoic acidRefChem:1057435DTXCID402370512-Oxo phytodienoic acid12-Oxo-pdarac 12-Oxophytodienoic Acid12-OPDA(15Z)-12-Oxophyto-10,15-dienoic acid
Show more names
Cmc_7397Cmc_13962(9S,13S,15Z)-12-Oxo-10,15-phytodienoic acidcis-(+)-12-Oxo-phytodienoic acid,100ug in 100ul EtOH4-oxo-5α-2Z-pentenyl)-2-cyclopentene-1α-octanoic acid8-[(1S,5S)-5-[(Z)-2-Pentenyl]-4-oxo-2-cyclopentenyl]octanoic acid8-[(1S,5S)-4-Oxo-5-[(Z)-2-pentenyl]-2-cyclopentenyl]octanoic acid
(9S,13S)-12-oxo-phytodienoic acid(1S,5S)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-octanoic acid12-Oxo-10,15(Z)-phytodienoic acid8-((1S,5S)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)octanoic acid(1S,2S)-3-oxo-2-(2'Z-pentenyl)cyclopent-4-eneoctanoic acid67204-66-48-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acido-Phytodienoic acid
Database identifiers
- CAS
85551-10-6- PubChem CID
- 5280411
- DTXSID
DTXSID6043705- ChEMBL
CHEMBL5641694- ChEBI
CHEBI:15560- Nikkaji
- J264.010D
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 11
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 382
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> 12-oxophytodienoic acid metabolites [FA0201]
Collision Cross Section179.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
Physicochemical properties
- Boiling point
- 447.7 · 447.7±24.0 °C(Predicted)
- Density
- 1.006 · 1.006±0.06 g/cm3(Predicted)
- storage temp.
- -80 °C, · Store at -80°C, protect from light
- solubility
- 25 mg/ml; · DMF: 25 mg/ml; DMSO: 15 mg/ml; Ethanol: 100 mg/ml; PBS pH 7.2: 2 mg/ml
- form
- Liquid
- pka
- 4.78 · 4.78±0.10(Predicted)
- color
- Colorless to light yellow
- Symbol(GHS)
- 2 · GHS02,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H350
- Precautionary statements
- 201 · P201-P202-P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P308+P313-P370+P378-P403+P235-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
- Hazard statements
- H225-H350
- Precautionary statements
- P201-P202-P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P308+P313-P370+P378-P403+P235-P405-P501
Chemistry & industry
Applications
Description12-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.
UsesThe 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.
Suppliers28 total
宜昌众意泰贸易有限公司0717-6449896 13886658719 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
风咏生物（AbMole）021-10000000 13000000000 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
北京沃凯生物科技有限公司010-62971590 18548936886 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
上海贝万塔生物科技有限公司021-67187366 19901745723 · [email protected]
湖北艾普蒂生物工程有限公司17762444226 · [email protected]
ChemeGen 中国18818260767 · [email protected]
广东翁江化学试剂有限公司0751-2815983 13927872582 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
Additional notes
DefinitionChEBI: (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.
Related reactions
1 records
Compound notes
Loading…