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SML0503

Sigma-Aldrich

9(S)-HODE

≥98% (HPLC)

Synonym(s):

9S-Hydroxy-10E,12Z-octadecadienoic acid

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About This Item

Empirical Formula (Hill Notation):
C18H32O3
CAS Number:
73543-67-6
Molecular Weight:
296.44
EC Number:
200-578-6
MDL number:
MFCD00065831
UNSPSC Code:
12352200
PubChem Substance ID:
329825451
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solution

concentration

1 mg/mL in ethanol

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

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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225 - H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

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[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.
Luciano De Petrocellis et al.
British journal of pharmacology, 167(8), 1643-1651 (2012-08-07)
Two oxidation products of linoleic acid, 9- and 13-hydroxy-octadecadienoic acids (HODEs), have recently been suggested to act as endovanilloids, that is, endogenous agonists of transient receptor potential vanilloid-1 (TRPV1) channels, thereby contributing to inflammatory hyperalgesia in rats. However, HODE activity
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
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
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