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H9146

Sigma-Aldrich

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

90-100 μg/mL in ethanol, ≥98%

Synonyme(s) :

13(S)-HODE

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About This Item

Formule empirique (notation de Hill):
C18H32O3
Numéro CAS:
29623-28-7
Poids moléculaire :
296.44
Numéro CE :
200-578-6
Numéro MDL:
MFCD00065833
Code UNSPSC :
12352200
ID de substance PubChem :
24895844
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98%

Concentration

90-100 μg/mL in ethanol

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

HNICUWMFWZBIFP-IRQZEAMPSA-N

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Conditionnement

Packaged under Argon.

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

57.2 °F

Point d'éclair (°C)

14 °C

Certificats d'analyse (COA)

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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
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
Ming-Yue Li et al.
American journal of respiratory cell and molecular biology, 43(6), 674-683 (2010-01-19)
Peroxisome proliferator-activated receptor (PPAR)-α and PPARγ participate in cell proliferation and apoptosis. Few studies have simultaneously investigated both PPARα and PPARγ in lung cancers in vivo. The roles of PPARα and -γ were investigated in the development of pulmonary tumors
Veronika Paluchova et al.
Molecular nutrition & food research, 64(11), e1901238-e1901238 (2020-04-12)
The docosahexaenoic acid ester of hydroxy linoleic acid (13-DHAHLA) is a bioactive lipid with anti-inflammatory properties from the family of fatty acid esters of hydroxy fatty acids (FAHFA). To explore the biosynthesis of 13-DHAHLA from dietary oils, C57BL/6N mice are
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