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SML0503

Sigma-Aldrich

9(S)-HODE

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C18H32O3
CAS-Nummer:
73543-67-6
Molekulargewicht:
296.44
EG-Nummer:
200-578-6
MDL-Nummer:
MFCD00065831
UNSPSC-Code:
51111800
PubChem Substanz-ID:
329825451
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solution

Konzentration

1 mg/mL in ethanol

Farbe

colorless to light yellow

Versandbedingung

wet ice

Lagertemp.

−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

InChIKey

NPDSHTNEKLQQIJ-UINYOVNOSA-N

Biochem./physiol. Wirkung

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.

Piktogramme

FlameExclamation mark
GHS02,GHS07

Signalwort

Danger

H-Sätze

H225,H319

Gefahreneinstufungen

Eye Irrit. 2 - Flam. Liq. 2

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 1

Flammpunkt (°F)

57.2 °F - closed cup

Flammpunkt (°C)

14.0 °C - closed cup

Analysenzertifikate (COA)

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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.
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
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
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
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
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