Anserine

Title: Anserine
CAS Registry Number: 584-85-0
CAS Name: N-b-Alanyl-3-methyl-L-histidine
Additional Names: a-(b-aminopropionylamino)-b-(1-methyl-5-imidazolyl)propionic acid; 3-methyl-N,a-(b-alanyl)-L-histidine
Molecular Formula: C10H16N4O3
Molecular Weight: 240.26
Percent Composition: C 49.99%, H 6.71%, N 23.32%, O 19.98%
Literature References: First found in muscles of geese, later in many more animals, but not in man, cow, horse, or dog. Isoln: Ackermann, Z. Physiol. Chem. 183, 1 (1929); Wolff, Wilson, J. Biol. Chem. 109, 565 (1935). Synthesis: Behrens, du Vigneaud, J. Biol. Chem. 120, 517 (1937); Rinderknecht et al., J. Org. Chem. 29, 1968 (1964). Review: M. Guggenheim, Die biogenen Amine (Karger, Basel & New York, 4th ed., 1951) pp 439-446, 502.
Derivative Type: L-Form
Properties: Needles from dil alc, dec 240-242°. [a]D30 +12.3° (c = 5). pK1 2.64; pK2 7.04; pK3 9.49. The dried material is very hygroscopic. Freely soluble in water. Slightly sol in methanol, even less in ethanol.
pKa: pK1 2.64; pK2 7.04; pK3 9.49
Optical Rotation: [a]D30 +12.3° (c = 5)
Derivative Type: Nitrate
Molecular Formula: C10H16N4O3.HNO3
Molecular Weight: 303.27
Percent Composition: C 39.60%, H 5.65%, N 23.09%, O 31.65%
Properties: Needles from dil methanol, mp 226-228°.
Melting point: mp 226-228°
Antazoline Antheridiol Anthiolimine Anthracene Anthragallol

Anserine
Anserine.png
Identifiers
CAS number 584-85-0 YesY
PubChem 112072
ChemSpider 100482 YesY
KEGG C01262 YesY
ChEBI CHEBI:18323 YesY
ChEMBL CHEMBL448301 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H16N4O3
Molar mass 240.25904
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anserine (beta-alanyl-N-methylhistidine) is a dipeptide found in the skeletal muscle and brain of mammals[1] and birds.

It is an antioxidant (about 5 times that of carnosine) and helps reduce fatigue.[citation needed]

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04, making it an effective buffer at physiologic pH.[2]