9-hydroxy-10E,12Z-octadecadienoic acid
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Basic information
- CAS
98524-19-7- Standard SMILES
CCCCC/C=C\C=C\C(O)CCCCCCCC(=O)O- InChIKey
NPDSHTNEKLQQIJ-ZJHFMPGASA-N- Molecular formula
- C18H32O3
- Average molar mass
- 296.4 g/mol
- Monoisotopic mass
- 296.23514488
Overview
9-HODE is a HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is an octadecadienoic acid and a HODE. It is a conjugate acid of a 9-HODE(1-).
Names & identifiers
- Preferred name
- 9-hydroxy-10E,12Z-octadecadienoic acid
- IUPAC
- (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
- English name
- (+/-)9-HODE
- Molecular formula
- C18H32O3
- Molecular weight
- 296.45
Names & synonyms
9-Hode98524-19-79-hydroxy-10E,12Z-octadecadienoic acid(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid9-hydroxy-trans-10,cis-12-octadecadienoic acid9-(E,Z)-Hode(10E,12Z)-9-Hydroxy-10,12-octadecadienoic acidXL87KT7C6ZCHEMBL1077284(+/-)9-HODE(10E,12Z)-9-HODE( inverted exclamation markA)9-HODE
Show more names
NPDSHTNEKLQQIJ-ZJHFMPGASA-N9-Hydroxyoctadecadienoic acidOleic Acid Impurity 63 (9-(E,Z)-HODE)(±)9-Hydroxyoctadeca-10E,12Z-dienoic acid(+/-)-9-HYDROXYOCTADECA-10E,12Z,DIENOIC ACID(+/-)-9-HYDROXY-10E,12Z-OCTADECADIENOIC ACID9-Hydroxy-trans-10,cis-12 octadecadienoic acid
9-Hydroxy-10-trans,12-cis-octadecadienoic acid9-Hydroxy-(10E,12Z)-octadeca-10,12-dienoic acid10,12-Octadecadienoic acid, 9-hydroxy-, (10E,12Z)-(?)9-HODEUNII-XL87KT7C6ZSCHEMBL122671BML2-D05orb1693626
Properties
Computed structural propertiesFilling in
- XLogP
- 5.3
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 14
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 295
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> Other Octadecanoids [FA0200]
Collision Cross Section
178.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
180.63 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
187.9 Ų [M+Na]+
Physicochemical properties
- Boiling point
- 416.1 · 416.1±33.0 °C(Predicted)
- Density
- 0.97 · 0.970±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 50 mg/ml; · DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS pH 7.2: 1 mg/ml
- form
- Clear to light-yellow liquid.
- pka
- 4.78 · 4.78±0.10(Predicted)
- FDA UNII
- 87 KT7C6Z · XL87KT7C6Z
- Symbol(GHS)
- 2 · GHS02,GHS07
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
Description(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.
Uses(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.
Uses(+/-)9-HODE is a distinct product of non-enzymatic linoleic acid oxidation.Also, it is one of the component in rice koji extract (RKE), which activates peroxisome proliferator-activated receptor alpha (PPARα).It is derived from Methyl Linoleate (M265190), which is a common methyl ester produced from soybean or canola oil and methanol. Methyl Linoleate is classified as a biodiesel due to its long methyl chain and is used as a fuel in standard diesel engines.
Additional notes
DefinitionChEBI: 9-HODE is a HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9. It has a role as a plant metabolite, a human metabolite and a mouse metabolite. It is a conjugate acid of a 9-HODE(1-).
Related reactions
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Compound notes
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