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Merck

H3023

Sigma-Aldrich

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

≥90% (HPLC), liquid, Ras/MAP pathway activitor

Synonym(e):

20-HETE, 20-Hydroxyarachidonic acid

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About This Item

Empirische Formel (Hill-System):
C20H32O3
CAS-Nummer:
Molekulargewicht:
320.47
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.77

product name

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

Assay

≥90% (HPLC)

Form

liquid

Konzentration

~100 μg/mL in ethanol

Versandbedingung

dry ice

Lagertemp.

−20°C

SMILES String

OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-

InChIKey

NNDIXBJHNLFJJP-DTLRTWKJSA-N

Biochem./physiol. Wirkung

20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid (20-HETE) is an arachidonic acid metabolite via cytochrome P4504A, that is an activator of the Ras/MAP (microtubule-associated protein) pathway. 20-HETE acid is a predominant arachidonic acid present in the kidney. It is involved in the regulation of sodium, potassium and chloride transport in the renal tubules. 20-HETE is often excreted in urine in the form of glucuronide conjugate and sometimes as free acids. Increased urine 20-HETE is observed during pregnancy in rats.

Verpackung

Packaged under argon.

Piktogramme

FlameExclamation mark

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Eye Irrit. 2 - Flam. Liq. 2

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 1

Flammpunkt (°F)

57.2 °F - closed cup

Flammpunkt (°C)

14.0 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Anne Barden et al.
Free radical biology & medicine, 42(11), 1730-1735 (2007-04-28)
There is considerable evidence that chronic moderate-to-high alcohol consumption increases blood pressure. The mechanisms by which this occurs are not clear. Alcohol consumption can induce oxidative stress and cytochrome P450 (CYP450) isoforms that are associated with oxidative stress and may
Jonas C Fordsmann et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(6), 2562-2570 (2013-02-09)
Cortical spreading depression (CSD) is associated with release of arachidonic acid, impaired neurovascular coupling, and reduced cerebral blood flow (CBF), caused by cortical vasoconstriction. We tested the hypothesis that the released arachidonic acid is metabolized by the cytochrome P450 enzyme
Tiago J Costa et al.
Frontiers in physiology, 9, 490-490 (2018-06-06)
Postmenopausal period has been associated to different symptoms such as hot flashes, vulvovaginal atrophy, hypoactive sexual desire disorder (HSDD) and others. Clinical studies have described postmenopausal women presenting HSDD can benefit from the association of testosterone to conventional hormonal therapy.
Elevated 12-and 20-hydroxyeicosatetraenoic acid in urine of patients with prostatic diseases
Nithipatikom K, et al.
Cancer Letters, 233(2), 219-225 (2006)
M M Muthalif et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(21), 12701-12706 (1998-10-15)
Norepinephrine (NE) and angiotensin II (Ang II), by promoting extracellular Ca2+ influx, increase Ca2+/calmodulin-dependent kinase II (CaMKII) activity, leading to activation of mitogen-activated protein kinase (MAPK) and cytosolic phospholipase A2 (cPLA2), resulting in release of arachidonic acid (AA) for prostacyclin

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