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2208-41-5

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2208-41-5 Usage

Description

6-hydroxy Melatonin is an active metabolite of melatonin . It is formed from melatonin by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes. 6-hydroxy Melatonin is a melatonin 1A (MT1A), MT1B, and MT2 receptor agonist. It inhibits dopamine release from isolated rabbit retina (IC50 = 0.0016 μM). 6-hydroxy Melatonin (10 and 100 μM) reduces increases in the levels of NF-κB, IL-6, and IL-8 and decreases in glutathione (GSH) levels in LPS- and peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an in vitro model of sepsis. It reduces iron-induced lipid oxidation in rat hippocampal homogenate when administered at a dose of 10 mg/kg.

Chemical Properties

Off-White to Pale Beige Solid

Uses

Different sources of media describe the Uses of 2208-41-5 differently. You can refer to the following data:
1. A major human metabolite of Melatonin
2. 6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes and keratinocytes.

Definition

ChEBI: A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.

General Description

6-Hydroxymelatonin (6-OHM) is a melatonin metabolite. It is produced in the liver by the action of cytochrome P450 enzyme as well as by photodegradation of melatonin. In the central nervous system, it exists as a sulfated form. 6-OHM is a partial melatonin receptor MT2 agonist.

Biochem/physiol Actions

6-Hydroxymelatonin (6-OHM) is an antioxidant with a free radical scavenging role. Like melatonin, it reduces the impact of UVB-induced oxidative stress in melanocytes. It also aids protection during iron (Fe2+)-induced neurotoxicity. 6-OHM effectively reduces lipid peroxidation and superoxide anion production induced by potassium cyanide (KCN).

Check Digit Verification of cas no

The CAS Registry Mumber 2208-41-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,0 and 8 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2208-41:
(6*2)+(5*2)+(4*0)+(3*8)+(2*4)+(1*1)=55
55 % 10 = 5
So 2208-41-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

2208-41-5Downstream Products

2208-41-5Relevant articles and documents

Further insights into the reaction of melatonin with hydroxyl radical

Horstman, Joseph A.,Wrona, Monika Z.,Dryhurst, Glenn

, p. 371 - 382 (2002)

Recent interest has focused on the use of exogenous melatonin as an antioxidant, particularly to scavenge the highly cytotoxic hydroxyl radical (HO?) which may be generated in many pathological conditions. However, in vitro and in vivo studies aimed at assessing the antioxidant properties of melatonin have produced conflicting results. While it is known that HO? reacts with melatonin at a diffusion limited rate, very little is known about the products of this reaction. In this investigation it is shown that incubation of melatonin with a Fenton-type HO?-generating system at pH 7.4 forms a complex mixture of primary products. These include 2-hydroxymelatonin, which was isolated as its more stable oxindole tautomer, 4- and 6-hydroxymelatonin, N-acetyl-N2-formyl-5-methoxykynurenine and 7,7′-bi-(5-methoxy-N-acetyltryptamine-4-one). Reaction pathways that might lead to these products are described. The differing biological effects of these products, while currently incompletely understood, might account for the controversy concerning the antioxidant properties of melatonin.

An efficient synthesis of 6-hydroxymelatonin, a human metabolite of melatonin

Karam, Omar,Zunino, Fabien,Chagnaut, Vincent,Jouannetaud, Marie Paule,Jacquesy, Jean Claude

, p. 1511 - 1513 (2007/10/03)

A four-step synthesis of 6-hydroxymelatonin 5, major human metabolite of melatonin 1, is reported starting from melatonin. The synthesis involves in the keys steps a regioselective Friedel-Crafts acylation followed by a Baeyer-Villiger oxidation. The overall yield is 48%.

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