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H3023

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

Name: 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid
Brand: SIGMA

≥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

Assay:

≥90% (HPLC)

Form:

liquid

Quality level:

200

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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

Bioactive Small Molecules

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.

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

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

0000518567

0000518566

0000513514

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Astrocytes drive cortical vasodilatory signaling by activating endothelial NMDA receptors.

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

Role of the CYP4A/20-HETE pathway in vascular dysfunction of the Dahl salt-sensitive rat.

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

Elevated 12-and 20-hydroxyeicosatetraenoic acid in urine of patients with prostatic diseases

Nithipatikom K, et al.

Cancer Letters, 233(2), 219-225 (2006)

Increased 20-HETE synthesis explains reduced cerebral blood flow but not impaired neurovascular coupling after cortical spreading depression in rat cerebral cortex.

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

A reduction in alcohol consumption is associated with reduced plasma F2-isoprostanes and urinary 20-HETE excretion in men.

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

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Global Trade Item Number

SKU	GTIN
H3023-10UG	04061833792544
H3023-50UG	04061838071132

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