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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

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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

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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

GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Precautionary Statements

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

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’.

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Changes in lipids composition and metabolism in colorectal cancer: a review.

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

5-/12-Lipoxygenase-linked cascade contributes to the IL-33-induced synthesis of IL-13 in mast cells, thus promoting asthma development.

MyungJa Ro et al.

Allergy, 73(2), 350-360 (2017-09-01)

As asthma progresses, the levels of IL-33 in serum are markedly increased and contribute to asthmatic development and exacerbation. Mast cells, one of the principal effector cells in the pathogenesis of asthma, express high levels of the IL-33 receptor ST2

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

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-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

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