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22030

L-Carnosine

Name: <SC>L</SC>-Carnosine
Brand: SIAL

≥99.0% (NT)

Synonym(s):

β-Alanyl-L-histidine

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₄N₄O₃

CAS Number:

305-84-0

Molecular Weight:

226.23

EC Number:

206-169-9

UNSPSC Code:

12352200

MDL number:

MFCD00005207

Beilstein/REAXYS Number:

87671

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Properties

assay

≥99.0% (NT)

optical activity

[α]20/D +21±1°, c = 1.5% in H₂O

mp

253 °C (dec.) (lit.), 258-260 °C (dec.)

storage temp.

2-8°C

SMILES string

NCCC(=O)N[C@@H](Cc1c[nH]cn1)C(O)=O

InChI

1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

InChI key

CQOVPNPJLQNMDC-ZETCQYMHSA-N

Description

Biochem/physiol Actions

L-Carosine is a dipeptide found at millimolar concentration in brain, muscle and the lens of the eye. In model systems it is a potent antioxidant that scavenges oxygen free radicals and transition metal ions. It blocks protein-protein and protein-DNA cross-links induced by hypochlorite anions and toxic aldehydes such as acetaldehyde, formaldehyde, and malondialdehyde, the primary product of lipid peroxidation. It also inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars and inhibits the formation of toxic advanced glycation end products (AGE). These activities make it of interest in studies of aging, atherosclerosis, Alzheimer′s disease, and the secondary effects of diabetes.

Dipeptide with potent antioxidant and antiglycation activity; blocks nonenzymatic glycosylation and protein cross-linking induced by reactive aldehydes.

Other Notes

Substrate for the assay of carnosinase

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