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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:
Molecular Weight:
296.44
EC Number:
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Danger

Hazard Statements

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


Certificates of Analysis (COA)

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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
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.
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

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