H7768

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

Name: 12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
Brand: SIGMA

~100 μg/mL in ethanol, ≥95% (HPLC)

Synonym(s):

(S)-12-HETE

Select a Size

All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₂O₃

CAS Number:

54397-83-0

Molecular Weight:

320.47

UNSPSC Code:

12352106

NACRES:

NA.77

PubChem Substance ID:

24895806

EC Number:

200-578-6

Beilstein/REAXYS Number:

2656104

MDL number:

MFCD00036916

Product Name

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

Looking for similar products? Visit Product Comparison Guide

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

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

55.4 °F

flash_point_c

13 °C

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000492662

0000482673

0000457670

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Changes in the levels of 12/15-lipoxygenase, apoptosis-related proteins and inflammatory factors in the cortex of diabetic rats and the neuroprotection of baicalein.

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

12-lipoxygenase promotes tumor progress by TGF-β1-mediated epithelial to mesenchymal transition and predicts poor prognosis in esophageal squamous cell carcinoma.

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

Metabolism pathways of arachidonic acids: mechanisms and potential therapeutic targets.

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

Bay11-7082 inhibits the disintegration of the lymphendothelial barrier triggered by MCF-7 breast cancer spheroids; the role of ICAM-1 and adhesion.

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

12(S)-hydroxyeicosatetraenoic acid impairs vascular endothelial permeability by altering adherens junction phosphorylation levels and affecting the binding and dissociation of its components in high glucose-induced vascular injury.

Xiaofang Wang et al.

Journal of diabetes investigation, 10(3), 639-649 (2018-09-27)

Diabetes is an important risk factor for atherosclerotic disease. The initiating factor of atherosclerosis is local endothelial cell injury. The arachidonic acid metabolite, 12(S)-hydroxyeicosatetraenoic acid (12[S]-HETE), might be involved in this process. In recent years, some studies have discussed the

View All Related Papers