3'-Adenylic Acid
Structural Formula Vector Image
Title: 3¢-Adenylic Acid
CAS Registry Number: 84-21-9
Additional Names: Adenosine 3¢-monophosphate; adenosine-3¢-phosphoric acid; adenosine-3¢-monophosphoric acid; adenylic acid b; yeast adenylic acid; synadenylic acid; h-adenylic acid
Molecular Formula: C10H14N5O7P
Molecular Weight: 347.22
Percent Composition: C 34.59%, H 4.06%, N 20.17%, O 32.25%, P 8.92%
Literature References: Early prepns from yeast nucleic acid: Levene, Bass, Nucleic Acids (Chemical Catalogue Co., New York, 1931). Early work probably done on mixtures of 2¢- and 3¢-adenylic acids; both compds isomerize readily to form an equilibrium mixture under acid conditions: Carter, Cohn, Fed. Proc. 8, 190 (1949); Baddily, in The Nucleic Acids vol. 1, E. Chargaff, J. N. Davidson, Eds. (Academic Press, New York, 1955) pp 165-168; A. M. Michelson, The Chemistry of Nucleosides and Nucleotides (Academic Press, New York, 1963) pp 100-106. Synthesis: Brown, Todd, J. Chem. Soc. 1952, 44. Structure of dihydrate: Brown et al., Nature 172, 1184 (1953); Sundaralingam, Acta Crystallogr. 21, 495 (1966). Reviews: see Adenosine.
Properties: Long, fine, colorless, needles. mp 197° (dec). Dihydrate, d (calc) 1.698. Absorption spectrum: Voet et al., Biopolymers 1, 193 (1963). Difficultly sol in boiling water. Gives quantitative yield of furfural when distilled with 20% HCl for 3 hrs (different from 5¢-adenylic acid which yields only traces). cf. Hoffman, J. Biol. Chem. 73, 15 (1927); Embden, Schmidt, Z. Physiol. Chem. 181, 130 (1929).
Melting point: mp 197° (dec)
Density: d (calc) 1.698

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