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H7768

Sigma-Aldrich

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

~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
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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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1 of 4

This Item
H1640H3023R7257
12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid ~100 μg/mL in ethanol, ≥95% (HPLC)

H7768

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

12(S)-Hydroxy-(5Z,8E,10E)-heptadecatrienoic acid ≥93% (HPLC), ethanol solution

H1640

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

20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid ~100 μg/mL in ethanol, ≥90% (HPLC)

H3023

20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid

Ricinoleic acid ≥95%

R7257

Ricinoleic acid

assay

≥95% (HPLC)

assay

≥93% (HPLC)

assay

≥90% (HPLC)

assay

≥95%

form

liquid

form

ethanol solution

form

liquid

form

liquid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

ambient

concentration

~100 μg/mL in ethanol

concentration

-

concentration

~100 μg/mL in ethanol

concentration

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    SLCG7542
    SLCG0200
    SLCF3760
    SLCF0795
    SLCD5718

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    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
    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
    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
    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
    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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