5'-Guanylic Acid
Title: 5¢-Guanylic Acid
CAS Registry Number: 85-32-5
Additional Names: Guanosine 5¢-monophosphate; GMP; guanosine 5¢-phosphate; guanine riboside-5-phosphoric acid
Molecular Formula: C10H14N5O8P
Molecular Weight: 363.22
Percent Composition: C 33.07%, H 3.89%, N 19.28%, O 35.24%, P 8.53%
Literature References: Nucleotide widely distributed in nature; found in hydrolyzates of RNA. Isolated together with inosinic acid from sardines or yeast extract: Kuninaka et al., New Food Ind. 3, no. 1, 21 (1961). Also by direct biosynthesis using microorganisms or enzymes: Abrams, Bentley, Arch. Biochem. Biophys. 79, 91 (1959); Magasanik, Karibian, J. Biol. Chem. 235, 2672 (1960); Okumura et al., US 3249511 (1966). Chemical synthesis: Michelson, Todd, J. Chem. Soc. 1949, 2483; Chambers et al., J. Am. Chem. Soc. 79, 3747 (1957); Gilham, Tener, Chem. Ind. (London) 1959, 542; Tener, J. Am. Chem. Soc. 83, 159 (1961); Koransky et al., Z. Naturforsch. 17B, 291 (1962). Prepn of Na salt: Ishibashi, Ito, US 3190877 (1965 to Takeda). Monograph on synthesis of nucleotides: G. R. Pettit, Synthetic Nucleotides vol. 1 (Van Nostrand Reinhold, New York, 1972) 252 pp. Reviews: See Guanidine.
Properties: Microcrystals, dec 190-200°. Sparingly sol in cold water.
 
Derivative Type: Barium salt octahydrate
Molecular Formula: C10H12N5O8PBa.8H2O
Molecular Weight: 642.65
Percent Composition: C 18.69%, H 4.39%, N 10.90%, O 39.83%, P 4.82%, Ba 21.37%
Properties: White powder. uv max (pH 2): 256 nm (e 12400); (pH 12): 260 nm (e 12100).
Absorption maximum: uv max (pH 2): 256 nm (e 12400); (pH 12): 260 nm (e 12100)
 
Derivative Type: Disodium salt monohydrate
Molecular Formula: C10H12N5O8PNa2.H2O
Molecular Weight: 425.20
Percent Composition: C 28.25%, H 3.32%, N 16.47%, O 33.87%, P 7.28%, Na 10.81%
Properties: Hygroscopic crystals, decomp at about 250°. Characteristic meaty taste. aM (molar absorbancy): 13.7 ´ 103 at 252.5 nm (pH 7). Soly in water at 25° about 25 g/100 ml. Practically insol in alcohol, acetone, ether.
Absorption maximum: aM (molar absorbancy): 13.7 ´ 103 at 252.5 nm (pH 7)
 
Use: The disodium salt as flavor intensifier, like sodium inosinate and sodium glutamate. Said to be more effective than either.

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