9-Oxo-10,12-octadecadienoic acid
Basic information
- CAS
54232-58-5- Standard SMILES
CCCCC/C=C/C=C/C(=O)CCCCCCCC(=O)O- InChIKey
LUZSWWYKKLTDHU-SIGMCMEVSA-N- Molecular formula
- C18H30O3
- Average molar mass
- 294.4 g/mol
- Monoisotopic mass
- 294.21949481
Overview
9-oxo-10E,12E-ODE is an oxooctadecadienoic acid that consists of 10E,12E-octadecadienoic acid with the oxo substituent located at position 9. It has a role as a metabolite. It is an enone and an oxooctadecadienoic acid.
Names & identifiers
- Preferred name
- 9-Oxo-10,12-octadecadienoic acid
- IUPAC
- (10E,12E)-9-oxooctadeca-10,12-dienoic acid
- English name
- 9-oxo-10(E),12(E)-Octadecadienoic Acid
- Molecular formula
- C18H30O3
- Molecular weight
- 294.43
Names & synonyms
9-Oxo-10,12-octadecadienoic acid9-Keto-10,12-octadecadienoic acid54665-32-69-Oxo-10,12-odda10,12-Octadecadienoic acid, 9-oxo-DTXSID80904330RefChem:914790DTXCID20133348854232-58-59-oxo-10(E),12(E)-Octadecadienoic Acid(10E,12E)-9-oxooctadeca-10,12-dienoic acid(10E,12E)-9-Oxo-10,12-octadecadienoic acid
Show more names
9-Oxooctadeca-10,12-dienoic acid10,12-Octadecadienoic acid, 9-oxo-, (10E,12E)-LUZSWWYKKLTDHU-SIGMCMEVSA-N
9-oxo-10E,12E-ODE10(E),12(E)-9-oxo-ODE9-oxo-10E,12E-octadecadienoic acid9-KODECompound NP-013728CHEMBL465240orb1680899SCHEMBL1234585
Database identifiers
- CAS
54232-58-5、54665-32-6- PubChem CID
- 5283011
- DTXSID
DTXSID301347858- ChEMBL
CHEMBL465240- ChEBI
CHEBI:72843- Nikkaji
- J767.169E、J834.677A
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 14
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 329
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> Other Octadecanoids [FA0200]
Collision Cross Section177.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
Physicochemical properties
- Boiling point
- 449.2 · 449.2±28.0 °C(Predicted)
- Density
- 0.966 · 0.966±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 16 mg/ml; · DMF: 16 mg/ml; DMSO: 16 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
- pka
- 4.77 · 4.77±0.10(Predicted)
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-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,GHS07
- 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
Chemistry & industry
Applications
Description9-oxo-10(E),12(E)-Octadecadienoic acid (9-oxoODA) is a natural agonist, abundant in tomatoes, that activates PPARα at 10-20 μM. It is produced from conjugated linoleic acid, which is also known to be a PPARα agonist. 9-oxoODA increases the expression of genes regulated by PPARα in primary mouse hepatocytes, altering lipid metabolism.
Uses(10E,12E)-9-Oxo-10,12-octadecadienoic acid (9-oxo-ODA) is a PPARα agonist that can be isolated from the basidiomycete Gomphus floccosus. (10E,12E)-9-Oxo-10,12-octadecadienoic acid enhances fatty acid oxidation through PPARα activation, thereby inhibiting triglyceride accumulation. (10E,12E)-9-Oxo-10,12-octadecadienoic acid also has antifungal (Fungal) activity[1][2].
Additional notes
DefinitionChEBI: 9-oxo-10E,12E-ODE is an oxooctadecadienoic acid that consists of 10E,12E-octadecadienoic acid with the oxo substituent located at position 9. It has a role as a metabolite. It is an oxooctadecadienoic acid and an enone.
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