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Merck

H7768

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

~100 μg/mL in ethanol, ≥95% (HPLC)

Sinónimos:

(S)-12-HETE

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Fórmula empírica (notación de Hill):
C20H32O3
Número CAS:
54397-83-0
Peso molecular:
320.47
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
24895806
EC Number:
200-578-6
Beilstein/REAXYS Number:
2656104
MDL number:
MFCD00036916

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Nombre del producto

12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid, ~100 μg/mL in ethanol, ≥95% (HPLC)

InChI key

ZNHVWPKMFKADKW-LQWMCKPYSA-N

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

SMILES string

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

assay

≥95% (HPLC)

form

liquid

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

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Packaging

Packaged under Argon.

Biochem/physiol Actions

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Clase de almacenamiento

3 - Flammable liquids

wgk

WGK 1

flash_point_f

55.4 °F

flash_point_c

13 °C

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Certificados de análisis (COA)

Lot/Batch Number
0000492662
0000492662
0000482673
0000482673
0000457670

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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
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
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
K Viola et al.
British journal of cancer, 108(3), 564-569 (2012-10-25)
Many cancers spread through lymphatic routes, and mechanistic insights of tumour intravasation into the lymphatic vasculature and targets for intervention are limited. The major emphasis of research focuses currently on the molecular biology of tumour cells, while still little is
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