ABC00442YR

7,8-Lactocyanocobalamin

7,8-Lactocyanocobalamin is a structurally modified cyanocobalamin derivative featuring a cyclic lactone moiety formed via intramolecular esterification between the 7-hydroxy and 8-carboxy groups of the corrin ring. This lactonization introduces a five-membered ฮณ-lactone ring, altering the parent drug's hydrophilicity and stability. The cobalt center retains its cyanide ligand, preserving the core coordination geometry. This impurity arises during oxidative degradation pathways of cyanocobalamin, particularly under acidic conditions. It serves as a critical HPLC reference standard for quantifying degradation products in pharmaceutical formulations.

On Request
Molecular Formula C63H85CoN13O15P
Molecular Weight 1354.3000
CAS Number 23208-66-4 โœ“ Verified
Purity N/A
Product Type API Impurity
Parent Drug Cyanocobalamin
Lead Time On Request
IUPAC Name [(2R)-1-[3-[(4S,5S,6R,7R,8R,9R,13S,18R,22R)-5,8-bis(2-amino-2-oxoethyl)-4,13,18-tris(3-amino-3-oxopropyl)-2,5,6,9,11,14,14,22-octamethyl-20-oxo-19-oxa-23,24,26-triaza-25-azanidahexacyclo[15.5.1.13,6.17,10.112,15.018,22]hexacosa-1,3(26),10,12(24),15,17(23)-hexaen-9-yl]propanoylamino]propan-2-yl] [(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] phosphate;cobalt(3+);cyanide
Official Reference Standards
Std Catalog # Quantity Price
USP 1A03270 โ†— 25 mg USD 1200.00

๐Ÿ“ Synonyms

Vitamin B12 c-lactone 23208-66-4 Cyanocobalamin Impurity F; Vitamin B12 c-lactone; 7ss,8ss-Lactocyanocobalamin;7b,8b-Lactocyanocobalamin; Coa-[a-(5,6-dimethylbenzimidazolyl)]-Coss-cyano-8ss-hydroxycobamic a,b,d,e,g-pentaamide c,8-?-lactone; Cyanocobalamin 7ss,8ss-lactone 7?, 8?-Lactosobamamide FV167409

๐Ÿ”ฌ Chemical Identifiers

CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)C(=C7[C@]8(CC(=O)O[C@]8(C(=N7)C=C9C([C@@H](C(=N9)C(=C4[N-]5)C)CCC(=O)N)(C)C)CCC(=O)N)C)C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[C-]#N.[Co+3]
InChI=1S/C62H87N12O15P.CN.Co/c1-29-20-37-38(21-30(29)2)74(28-69-37)56-51(83)52(39(27-75)86-56)89-90(84,85)88-31(3)26-68-47(81)17-18-58(8)36(22-45(66)79)55-61(11)59(9,24-46(67)80)35(13-15-43(64)77)50(73-61)33(5)54-60(10)25-48(82)87-62(60,19-16-44(65)78)41(71-54)23-40-57(6,7)34(12-14-42(63)76)49(70-40)32(4)53(58)72-55;1-2;/h20-21,23,28,31,34-36,39,51-52,55-56,75,83H,12-19,22,24-27H2,1-11H3,(H13,63,64,65,66,67,68,70,71,72,73,76,77,78,79,80,81,84,85);;/q;-1;+3/p-2/t31-,34-,35-,36+,39-,51-,52-,55-,56+,58-,59+,60-,61+,62+;;/m1../s1
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