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H3023

Sigma-Aldrich

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

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

Sinónimos:

20-HETE, 20-Hydroxyarachidonic acid

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About This Item

Fórmula empírica (notación de Hill):
C20H32O3
Número de CAS:
79551-86-3
Peso molecular:
320.47
MDL number:
MFCD00171542
UNSPSC Code:
12352106
PubChem Substance ID:
24895546
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

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

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_germany

WGK 1

flash_point_f

57.2 °F - closed cup

flash_point_c

14.0 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Elevated 12-and 20-hydroxyeicosatetraenoic acid in urine of patients with prostatic diseases
Nithipatikom K, et al.
Cancer Letters, 233(2), 219-225 (2006)
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.
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
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