Hydroxocobalamin
Title: Hydroxocobalamin
CAS Registry Number: 13422-51-0
CAS Name: Cobinamide hydroxide dihydrogen phosphate (ester) inner salt 3¢-ester with 5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
Additional Names: a-(5,6-dimethylbenzimidazolyl)hydroxocobamide; vitamin B12a; hydroxocobemine; OHB12
Trademarks: Cobalin-H (Link); Dodécavit (Serb); Duradoce (Atlantis); Neo-Cytamen (Medeva); Redisol H (Merck & Co.)
Molecular Formula: C62H89CoN13O15P
Molecular Weight: 1346.36
Percent Composition: C 55.31%, H 6.66%, Co 4.38%, N 13.52%, O 17.83%, P 2.30%
Literature References: Physiological analog of vitamin B12 where the CN group is replaced with OH. Exists in aq soln as an equilibrium mixture of the hydroxy isomer and the ionic aqua isomer (aquacobalamin). Precursor of the coenzymes methylcobalamin and cobamamide, q.q.v. Prepn: E. A. Kaczka et al., J. Am. Chem. Soc. 71, 1514 (1949); eidem, ibid. 73, 335 (1951); eidem, US 2738301 (1956 to Merck & Co.). Acids replace the hydroxo group with the anion of the acid: eidem, Science 112, 354 (1950). Prepn from cyanocobalamin: R. Bieganowski, G. Klar, Chem. Ztg. 106, 235 (1982). Clinical evaluation as antidote to cyanide: J. C. Forsyth et al., Clin. Toxicol. 31, 277 (1993). Review: "Vitamin B12" in Vitamins, W. Friedrich, Ed. (de Gruyter, Berlin, 1988) pp 837-928.
Properties: Dark red, orthorhombic needles or platelets from water + acetone. Darkens at 200°, but not melted at 300°. Absorption max (H2O): 279, 325, 359, 516, 537 nm (e 19000, 11400, 20600, 8900, 9500). Moderately sol in water and in the lower aliphatic alcohols. Practically insol in acetone, ether, petr ether, halogenated hydrocarbons, benzene.
Absorption maximum: Absorption max (H2O): 279, 325, 359, 516, 537 nm (e 19000, 11400, 20600, 8900, 9500)
 
Derivative Type: Aquacobalamin
CAS Registry Number: 13422-52-1
CAS Name: Cobinamide hydroxide monohydrate dihydrogen phosphate (ester) inner salt 3¢-ester with 5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
Additional Names: aquocobalamin; vitamin B12b; vitamin B12d
Molecular Formula: C62H90CoN13O15P.OH
Molecular Weight: 1364.37
Percent Composition: C 54.58%, H 6.72%, Co 4.32%, N 13.35%, O 18.76%, P 2.27%
Properties: Absorption max (H2O): 274, 317, 351, 499, 527 nm (e 20600, 6100, 26500, 8100, 8500).
Absorption maximum: Absorption max (H2O): 274, 317, 351, 499, 527 nm (e 20600, 6100, 26500, 8100, 8500)
 
Derivative Type: Acetatocobalamin
CAS Registry Number: 22465-48-1
Additional Names: Cobinamide acetate (salt) dihydrogen phosphate (ester) inner salt 3¢-ester with 5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
Trademarks: Depogamma (Woerwag); Docelan (Aventis); Novidroxin (Fatol)
Molecular Formula: C64H91CoN13O16P
Molecular Weight: 1388.39
Percent Composition: C 55.37%, H 6.61%, Co 4.24%, N 13.11%, O 18.44%, P 2.23%
Literature References: Prepn of stable solns: Marcus et al., FR 1336671 (1963 to Merck & Co.), C.A. 60, 380a (1964).
 
Derivative Type: Nitrocobalamin
CAS Registry Number: 20623-13-6
CAS Name: Cobinamide nitrite (salt) dihydrogen phosphate (ester) inner salt 3¢-ester with 5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
Additional Names: nitritocobalamin; vitamin B12c
Molecular Formula: C62H88CoN14O16P
Molecular Weight: 1375.35
Percent Composition: C 54.14%, H 6.45%, Co 4.28%, N 14.26%, O 18.61%, P 2.25%
Literature References: Prepn: E. A. Kaczka et al., J. Am. Chem. Soc. 73, 3569 (1951).
Properties: Red crystalline solid. Absorption max in water: 352, 527.5 nm (E1%1cm 153.2, 59.5); in 0.01N NaOH: 357, 535 nm (E1%1cm 139, 62.5).
Absorption maximum: Absorption max in water: 352, 527.5 nm (E1%1cm 153.2, 59.5); in 0.01N NaOH: 357, 535 nm (E1%1cm 139, 62.5)
 
Derivative Type: Sulfitocobalamin
CAS Registry Number: 15671-27-9
CAS Name: Cobinamide sulfite (1:1) (salt) dihydrogen phosphate (ester) inner salt 3¢-ester with 5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole
Additional Names: cobalaminsulfonic acid
Molecular Formula: C62H89CoN13O17PS
Molecular Weight: 1410.42
Percent Composition: C 52.80%, H 6.36%, Co 4.18%, N 12.91%, O 19.28%, P 2.20%, S 2.27%
Literature References: Prepn: Fricke, US 2721162 (1955 to Abbott).
Properties: Absorption max: 275, 365, 418, 516 nm (E1%1cm 328, 130, 49, 61).
Absorption maximum: Absorption max: 275, 365, 418, 516 nm (E1%1cm 328, 130, 49, 61)
 
Therap-Cat: Vitamin (hematopoietic).
Therap-Cat-Vet: Vitamin (hematopoietic).
Keywords: Vitamin/Vitamin Source; Vitamin B12.

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