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

hazcat

Eye Irrit. 2 - Flam. Liq. 2

storage_class_code

3 - Flammable liquids

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

[Activation mechanism of PPARgamma by its endogenous ligands].
Takuma Shiraki
Seikagaku. The Journal of Japanese Biochemical Society, 79(10), 960-964 (2007-11-22)
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....
N Marx et al.
Arteriosclerosis, thrombosis, and vascular biology, 19(3), 546-551 (1999-03-12)
Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1...
Holger Hübke et al.
Journal of agricultural and food chemistry, 53(5), 1556-1562 (2005-03-03)
The analysis of (R)-9- and (S)-9-hydroxy-10E,12Z-octadecadienoic acid as well as (R)-13- and (S)-13-hydroxy-9Z,11E-octadecadienoic acid (HODE) as free acids, esterified in triacylglycerols (storage lipids), and esterified in polar lipids (phospholipids, glycolipids, etc.) in barley, germinating barley, and finished malt was performed...
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....

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