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Merck
CN

H3023

Sigma-Aldrich

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
MDL number:
MFCD00171542
UNSPSC Code:
12352106
PubChem Substance ID:
24895546
NACRES:
NA.77

Key Documents

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Product Name

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

Quality Level

200

Assay

≥90% (HPLC)

form

liquid

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−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-

InChI key

NNDIXBJHNLFJJP-DTLRTWKJSA-N

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

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)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000394997
0000394997
0000304032
0000304032
0000278680

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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)
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
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
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
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