SML0503

Sigma-Aldrich

9(S)-HODE

≥98% (HPLC)

Synonym(s):
9S-Hydroxy-10E,12Z-octadecadienoic acid
Empirical Formula (Hill Notation):
C18H32O3
CAS Number:
Molecular Weight:
296.44
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

ethanol solution (1 mg/mL)

color

colorless to light yellow

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCC/C=C\C=C\[C@@H](O)CCCCCCCC(O)=O

InChI

1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1

InChI key

NPDSHTNEKLQQIJ-UINYOVNOSA-N

Packaging

100, 500 μg in glass bottle

Biochem/physiol Actions

9(S)-HODE is produced by the lipoxygenation of linoleic acid. It is a major component of plasma oxidized low-density lipoprotein. 9-HODE has been shown to stimulate cell proliferation and and extracellular matrix synthesis in human mesangial cells via PPARgamma. Pro-inflammatory effects of 9-HODE, acting through the receptor GPR132, can contribute to atherosclerosis progression. 9-HODE has also been shown to activate spinal TRPV1, leading to inflammatory hyperalgesia.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Certificate of Analysis
Certificate of Origin
Markus K Muellner et al.
The Biochemical journal, 420(2), 277-281 (2009-03-07)
LOOHs (lipid hydroperoxides) in oxLDL [oxidized LDL (low-density lipoprotein)] are potentially atherogenic compounds. Recently, H2S was identified as the third endogenous gasotransmitter in the vasculature. H2O2 is known to be destroyed by H2S. Assuming that H2S may also react with...
Edgar B Cahoon et al.
The Journal of biological chemistry, 279(13), 12495-12502 (2004-01-14)
Dimorphecolic acid (9-OH-18:2Delta(10)(trans)(,12)(trans)) is the major fatty acid of seeds of Dimorphotheca species. This fatty acid contains structural features that are not typically found in plant fatty acids, including a C-9 hydroxyl group, Delta(10),Delta(12)-conjugated double bonds, and trans-Delta(12) unsaturation. Expressed...
Frédéric Coutant et al.
Journal of immunology (Baltimore, Md. : 1950), 172(1), 54-60 (2003-12-23)
Because of its oxidative modification during the acute-phase response to an aggression, low density lipoprotein (LDL) can be regarded as a source of lipid mediators that can act both to promote and inhibit inflammation. This can be exemplified by the...
Audrey J Gaskins et al.
The American journal of clinical nutrition, 92(6), 1461-1467 (2010-10-15)
A Mediterranean diet has been associated with a reduced risk of cardiovascular disease and mortality. A possible mechanism is through a decrease in lipid peroxidation (LPO); however, evidence linking the Mediterranean diet with lower LPO in premenopausal women is sparse....
Shasha Li et al.
Scientific reports, 8(1), 14627-14627 (2018-10-04)
Zhenwu decoction (ZWD) is a promising traditional Chinese prescription against renal fibrosis, while its underlying mechanism remains unclear. Rat model of renal fibrosis were established and divided into control group, model group, ZWD treatment group and enalapril maleate treatment group....

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