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Merck
CN

H3023

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

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

Synonym(s):

20-HETE, 20-Hydroxyarachidonic acid

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About This Item

Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
79551-86-3
Molecular Weight:
320.47
UNSPSC Code:
12352106
PubChem Substance ID:
24895546
NACRES:
NA.77
MDL number:
MFCD00171542

Key Documents

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Product Name

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

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-

InChI key

NNDIXBJHNLFJJP-DTLRTWKJSA-N

assay

≥90% (HPLC)

form

liquid

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Related Categories

Biochem/physiol Actions

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.

Packaging

Packaged under argon.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

57.2 °F - closed cup

flash_point_c

14.0 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000518566
0000518567
0000518567
0000518566
0000513514

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Lingling Lu et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 39(3), 481-496 (2017-10-27)
Astrocytes express neurotransmitter receptors that serve as sensors of synaptic activity and initiate signals leading to activity-dependent local vasodilation and increases in blood flow. We previously showed that arteriolar vasodilation produced by activation of cortical astrocytes is dependent on endothelial
Kathleen M Lukaszewicz et al.
Clinical science (London, England : 1979), 124(12), 695-700 (2013-02-27)
20-HETE (20-hydroxyeicosatetraenoic acid), a vasoconstrictor metabolite of arachidonic acid formed through the action of CYP4A (cytochrome P450-4A) in vascular smooth muscle cells, has been implicated in the development of hypertension and vascular dysfunction. There have been a number of reports
K G Maier et al.
Current opinion in nephrology and hypertension, 10(1), 81-87 (2001-02-24)
Recent studies indicate that arachidonic acid is primarily metabolized by cytochrome P450 enzymes of the 4A and 2C families in the kidney to 20-hydroxyeicosatetraenoic acid (HETE), epoxyeicosatrienoic acids (EETs) and dihydroxyeicosatrienoic acids. These compounds play central roles in the regulation
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)
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