H9146

Sigma-Aldrich

13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid

90-100 μg/mL in ethanol, ≥98%

Synonym(s):
13(S)-HODE
Empirical Formula (Hill Notation):
C18H32O3
CAS Number:
Molecular Weight:
296.44
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥98%

concentration

90-100 μg/mL in ethanol

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

InChI key

HNICUWMFWZBIFP-IRQZEAMPSA-N

Biochem/physiol Actions

Expression of 15-lipoxygenase-1 (15-LOX-1) and its main product, 13(S)-HODE, are decreased in human colorectal and esophageal cancers. Certain non-steroidal anti-inflammatory drugs (NSAIDs) can induce apoptosis in human colon cancer cells by increased expression of 15-LOX-1, which down-regulates PPAR-delta through 13-HODE.
PPARγ agonist

Features and Benefits

This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Packaged under Argon.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol

WGK Germany

WGK 1

Flash Point(F)

57.2 °F

Flash Point(C)

14 °C

Claus Schneider et al.
Cancer metastasis reviews, 30(3-4), 277-294 (2011-10-18)
Cancer initiation and progression are multistep events that require cell proliferation, migration, extravasation to the blood or lymphatic vessels, arrest to the metastatic site, and ultimately secondary growth. Tumor cell functions at both primary or secondary sites are controlled by...
Ulaganathan Mabalirajan et al.
Journal of applied physiology (Bethesda, Md. : 1985), 107(4), 1285-1292 (2009-07-25)
We showed recently that IL-4 causes mitochondrial dysfunction in allergic asthma. IL-4 is also known to induce 12/15-lipoxygenase (12/15-LOX), a potent candidate molecule in asthma. Because vitamin E (Vit-E) reduces IL-4 and inhibits 12/15-LOX in vitro, here we tested the...
Anna Z Pollack et al.
American journal of epidemiology, 175(7), 645-652 (2012-02-04)
Exposures to cadmium, lead, and mercury are associated with adverse health effects, including cardiovascular disease, which may be promoted by lipid peroxidation. The authors examined cadmium, lead, and mercury in relation to plasma levels of F(2)-8α isoprostanes (isoprostane), 9-hydroperoxy-10,12-octadecadienoic acid...
Wei Liu et al.
Chemical research in toxicology, 23(5), 986-995 (2010-04-29)
The primary products from peroxidation of linoleate in biological tissues and fluids are the hydroperoxy octadecadienoates, and the products normally assayed, after reduction of the hydroperoxides, are the corresponding hydroxy octadecadienoates (HODEs). The HODEs are found in tissues and fluids...
Igor Ivanov et al.
Proteins, 80(3), 703-712 (2011-12-23)
Mammalian lipoxygenases (LOXs) have been implicated in cellular defense response and are important for physiological homeostasis. Since their discovery, LOXs have been believed to function as monomeric enzymes that exhibit allosteric properties. In aqueous solutions, the rabbit 12/15-LOX is mainly...

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