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H7768

Sigma-Aldrich

12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid

~100 μg/mL in ethanol, ≥95% (HPLC)

Synonyme(s) :

(S)-12-HETE

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About This Item

Formule empirique (notation de Hill):
C20H32O3
Numéro CAS:
54397-83-0
Poids moléculaire :
320.47
Beilstein:
2656104
Numéro CE :
200-578-6
Numéro MDL:
MFCD00036916
Code UNSPSC :
12352106
ID de substance PubChem :
24895806
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Essai

≥95% (HPLC)

Forme

liquid

Concentration

~100 μg/mL in ethanol

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

Clé InChI

ZNHVWPKMFKADKW-LQWMCKPYSA-N

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Actions biochimiques/physiologiques

12(S)-HETE is a bioactive lipid implicated in angiogenesis, growth, and metastasic action in tumor cell lines and in animal models. Arachidonate 12-lipoxygenase (12-LOX) converts arachidonic acid to 12(S)-(HETE). Alteration in 12-LOX expression or activity has been reported in various carcinomas including prostate carcinoma.
Prometastatic metabolite of arachidonic acid via the 12-lipoxygenase pathway that is expressed in many tumor cell lines. It is produced in coronary microvasculature and is a potent inducer of relaxation and hyperpolarization of these microvessels. It activates large-conductance Ca2+-activated K+ currents in coronary microvascular smooth muscle.

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)

55.4 °F

Point d'éclair (°C)

13 °C

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Certificats d'analyse (COA)

Lot/Batch Number
0000393443
0000393443
SLCG7542
SLCG0200
SLCF3760

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Consulter la Bibliothèque de documents

Yuke Li et al.
Free radical biology & medicine, 134, 239-247 (2019-01-20)
This study was designed to investigate the neuroprotective effects of baicalein and the effect of the cortical 12/15-lipoxygenase (12/15-LOX) pathway on diabetic cognitive dysfunction. Our results showed that spatial learning and memory ability, as well as cortex neurons, were significantly
Yan Qu et al.
Cancer management and research, 11, 8303-8313 (2019-10-02)
To clarify the effect of 12-lipoxygenase/12-hydroxyeicosatetraeonic acid (12-LOX/12-HETE) on progress of esophageal squamous cell carcinoma (ESCC) and the possible mechanism. We performed cell experiments including chemical treatment, transfection, Western blotting and transwell assay to investigate the function of 12-LOX/12-HETE. Slices
Alicja Pakiet et al.
Lipids in health and disease, 18(1), 29-29 (2019-01-28)
Altered metabolism of lipids is currently considered a hallmark characteristic of many malignancies, including colorectal cancer (CRC). Lipids are a large group of metabolites that differ in terms of their fatty acid composition. This review summarizes recent evidence, documenting many
Bei Wang et al.
Signal transduction and targeted therapy, 6(1), 94-94 (2021-02-28)
The arachidonic acid (AA) pathway plays a key role in cardiovascular biology, carcinogenesis, and many inflammatory diseases, such as asthma, arthritis, etc. Esterified AA on the inner surface of the cell membrane is hydrolyzed to its free form by phospholipase
C Vonach et al.
British journal of cancer, 105(2), 263-271 (2011-06-02)
The intravasation of breast cancer into the lymphendothelium is an early step of metastasis. Little is known about the mechanisms of bulky cancer invasion into lymph ducts. To particularly address this issue, we developed a 3-dimensional co-culture model involving MCF-7
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