H9146
13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid
90-100 μg/mL in ethanol, ≥98%
Synonym(s):
13(S)-HODE
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About This Item
Empirical Formula (Hill Notation):
C18H32O3
CAS Number:
Molecular Weight:
296.44
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk_germany
WGK 1
flash_point_f
57.2 °F
flash_point_c
14 °C
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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
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
Shing Hwa Liu et al.
British journal of pharmacology, 160(8), 1963-1972 (2010-07-24)
Peroxisome proliferator-activated receptor-gamma (PPAR-gamma), COX-2 and 15-lipoxygenase (LOX)-1 have been shown to be involved in tumour growth. However, the roles of PPAR-gamma, COX-2 or 15-LOX-1 in gastric tumourigenesis remain unclear. Here, we investigate the role of 15-LOX-1 induction by honokiol
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