Skip to Content
Merck
All Photos(1)

Documents

H7768

Sigma-Aldrich

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

~100 μg/mL in ethanol, ≥95% (HPLC)

Synonym(s):

(S)-12-HETE

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
54397-83-0
Molecular Weight:
320.47
Beilstein:
2656104
EC Number:
200-578-6
MDL number:
MFCD00036916
UNSPSC Code:
12352106
PubChem Substance ID:
24895806
NACRES:
NA.77

Quality Level

200

Assay

≥95% (HPLC)

form

liquid

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI key

ZNHVWPKMFKADKW-LQWMCKPYSA-N

Looking for similar products? Visit Product Comparison Guide

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.

Packaging

Packaged under Argon.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

55.4 °F

Flash Point(C)

13 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

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
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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service