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Merck

V2876

Vitamin B12

≥98%

Synonym(s):

α-(5,6-Dimethylbenzimidazolyl)cyanocobamide, CN-Cbl, Cyanocob(III)alamin, Cyanocobalamin

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About This Item

Empirical Formula (Hill Notation):
C63H88CoN14O14P
CAS Number:
68-19-9
Molecular Weight:
1355.37
PubChem Substance ID:
57654727
eCl@ss:
34058004
UNSPSC Code:
12352205
NACRES:
NA.79
EC Number:
200-680-0
Beilstein/REAXYS Number:
4122889

Key Documents

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Product Name

Vitamin B12, ≥98%

InChI key

RMRCNWBMXRMIRW-QJRSUKKJSA-L

InChI

1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57?,59-,60+,61+,62+;;/m1../s1

SMILES string

C/C(C1=N[C@]([C@]([C@H](CC(N)=O)[C@@]/2(C)CCC(NC[C@@H](OP([O-])(O[C@H]3[C@@H](O)[C@@H](N4C=[N]5C6=C4C=C(C)C(C)=C6)O[C@@H]3CO)=O)C)=O)([H])N([Co+]5C#N)C2=C(C)/C([C@@H](CCC(N)=O)C/7(C)C)=NC7=C/8)(C)[C@@](C)(CC(N)=O)[C@@H]1CCC(N)=O)=C9N=C8[C@@H](CCC(N)=O)[C@

assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

red to brown

storage temp.

2-8°C

Quality Level

200

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Application

Vitamin B12 has been used:
  • as a constituent in vitamin mix solution in in vitro gut simulator
  • as a standard in size exclusion inductively coupled plasma mass spectroscopy (SEC-ICP-MS)
  • as a constituent of simulated plasma protein mixture for Raman spectra analysis
  • in surface plasmon resonance (SPR) analysis
  • as a medium supplement in neonatal rat ventricular myocytes (NRVM)

Biochem/physiol Actions

Vitamin B12 (cobalamin) refers to a group of chemically-related cobalt containing molecules involved in cell processes such as DNA synthesis, fatty acid synthesis, energy production and regulation. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms. Bacteria-derived hydroxocobalamin (OHCbl) and CNCbl are converted in humans to useful coenzyme forms to support metabolic processes such as mitochondrial methylmalonylcoenzyme A mutase conversion of methylmalonic acid (MMA) to succinate to link lipid and carbohydrate metabolism, and activation of methionine synthase, the rate limiting step in the synthesis of methionine.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ6029
MKCN3478
WXBD2315V
WXBD1466V
MKCK8137

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Speciation of zinc in fish feed by size exclusion chromatography coupled to inductively coupled plasma mass spectrometry-Using fractional factorial design for method optimization and mild extraction conditions
Silva MS, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1104, 262-268 (2018)
Raman spectroscopic analysis of high molecular weight proteins in solution-considerations for sample analysis and data pre-processing
Parachalil DR, et al.
Analyst, 143(24), 5987-5998 (2018)
A missense mutation in TCN2 is associated with decreased risk for congenital heart defects and may increase cellular uptake of vitamin B12 via Megalin
Li P, et al.
Oncotarget, 8(33), 55216-55216 (2017)
Recombinant human collagen-based microspheres mitigate cardiac conduction slowing induced by adipose tissue-derived stromal cells
Smit NW, et al.
PLoS ONE, 12(8), e0183481-e0183481 (2017)
Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1
Koh A, et al.
Cell, 175(4), 947-961 (2018)
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