Title: Desthiobiotin
CAS Registry Number: 533-48-2
CAS Name: (4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid
Additional Names: 5-methyl-2-oxo-4-imidazolidinecaproic acid; e-(4-methyl-5-imidazolidone-2)-caproic acid; 4-methyl-5-(w-carboxyamyl)imidazolidone-2
Molecular Formula: C10H18N2O3
Molecular Weight: 214.26
Percent Composition: C 56.06%, H 8.47%, N 13.07%, O 22.40%
Literature References: Prepd from biotin by hydrogenolysis of the sulfide linkage: du Vigneaud et al., J. Biol. Chem. 146, 475 (1942). Improved prepn procedure: Melville et al., Science 98, 497 (1943). Synthesis: Melville, J. Am. Chem. Soc. 66, 1422 (1944); Wood, du Vigneaud, ibid. 67, 210 (1945); Duschinsky, Dolan, ibid. 2079; Bourquin et al., Helv. Chim. Acta 28, 528 (1954).
Properties: Long needles from water. mp 156-158°. [a]D21 +10.7° (c = 2). Sol in water.
Melting point: mp 156-158°
Optical Rotation: [a]D21 +10.7° (c = 2)
Derivative Type: Methyl ester
Molecular Formula: C11H20N2O3
Molecular Weight: 228.29
Percent Composition: C 57.87%, H 8.83%, N 12.27%, O 21.03%
Properties: Crystals from methanol. Can be sublimed at 10-5 mm and 100°. mp 69-70°. [a]D28 +2.6° (c = 2 in chloroform). Readily sol in chloroform.
Melting point: mp 69-70°
Optical Rotation: [a]D28 +2.6° (c = 2 in chloroform)
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