9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid
Basic information
- CAS
29774-12-7- Standard SMILES
CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O)OO- InChIKey
JGUNZIWGNMQSBM-UINYOVNOSA-N- Molecular formula
- C18H32O4
- Average molar mass
- 312.4 g/mol
- Monoisotopic mass
- 312.2300595
Overview
9(S)-HPODE is an HPODE (hydroperoxy-octadecadienoic acid) in which the double bonds are at positions 10 and 12 (E and Z geometry, respectively) and the hydroperoxy group is at position 9 (S configuration). It is an intermediate in the metabolic pathway for linoleic acid. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is functionally related to a (10E,12Z)-octadecadienoic acid. It is a conjugate acid of a 9(S)-HPODE(1-). It is an enantiomer of a 9(R)-HPODE.
Names & identifiers
- Preferred name
- 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid
- IUPAC
- (9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
- English name
- 9(S)-HPODE
- Molecular formula
- C18H32O4
- Molecular weight
- 312.44
Names & synonyms
9(S)-HPODE29774-12-79(S)-HPOD(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acidCHEBI:34498DTXSID4012340649(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acidRefChem:1074801DTXCID401665259(10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
Show more names
9-HPOD9(S) HpODE,9(S)HpODEJGUNZIWGNMQSBM-UINYOVNOSA-N9-S-Hydroperoxy linoleic acidOleic Acid Impurity 70 (9(S)-HPODE)9(S)-HYDROPEROXYOCTA- DECA-10E, 12Z-DIENOIC ACID9(S)-Hydroperoxy-trans-10,cis-12-octadecadienoic acid
9-S-Hpode9S-HpODE5BG4GR6GTM9-D-Hydroperoxylinoleic acid9-Hydroperoxylinoleic acid, (+)-UNII-5BG4GR6GTMLinoleic acid 9-hydroperoxide, (9S)-9S-hydroperoxy-10E,12Z-octadecadienoic acid
Database identifiers
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 15
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 310
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> Other Octadecanoids [FA0200]
Physicochemical properties
- Boiling point
- 447.7 · 447.7±38.0 °C(Predicted)
- Density
- 1.002 · 1.002±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
- Liquid.
- pka
- 4.78 · 4.78±0.10(Predicted)
- color
- Colorless to light yellow
- FDA UNII
- 5 BG4GR6GTM · 5BG4GR6GTM
- 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
Uses9(S)-HpODE is produced by the action of arachidonate 5-LO on linoleic acid. It can be further metabolized by potato hydroperoxide dehydratase to colneleic acid.
Additional notes
DefinitionChEBI: An HPODE (hydroperoxy-octadecadienoic acid) in which the double bonds are at positions 10 and 12 (E and Z geometry, respectively) and the hydroperoxy group is at position 9 (S configuration). It is an inte mediate in the metabolic pathway for linoleic acid.
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