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V900445

Sigma-Aldrich

Vitamin B12

Vetec™, reagent grade, ≥98%

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Synonym(s):
α-(5,6-Dimethylbenzimidazolyl)cyanocobamide, CN-Cbl, Cyanocob(III)alamin, Cyanocobalamin
Empirical Formula (Hill Notation):
C63H88CoN14O14P
CAS Number:
68-19-9
Molecular Weight:
1355.37
Beilstein:
4122889
EC Number:
200-680-0
PubChem Substance ID:
329829850

grade

reagent grade

product line

Vetec™

Assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

red to brown

storage temp.

2-8°C

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@

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

InChI key

RMRCNWBMXRMIRW-QJRSUKKJSA-L

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General description

Vitamin B12 is a water-soluble vitamin present in dietary sources including milk products, eggs, fish and meat. Vitamin B12, also called as cyanocobalamin, binds to protein transcobalamins. Structurally vitamin B12 has two pyrrole rings. The two forms comprise methylcobalamin or 5-deoxyadenosyl cobalamin, which are bioavailable.

Biochem/physiol Actions

Vitamin B12 plays a key role in DNA synthesis and methylation proteins. The intrinsic factor is essential for its circulation and reabsorption. Vitamin B12 coordinates with folic acid in the synthesis of red blood cells as well as in maintaining iron levels. It is essential for cellular energy production and serves as a cofactor for L-methyl malonyl-CoA mutase and methionine synthase. Vitamin B12 deficiency leads to pernicious anemia, megaloblastic anemia and neural tube defects.

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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Vitamin B12 in health and disease
O Leary F and Samman S
Nutrients, 2(3), 299-316 (2010)
Vitamin B12-A brief overview.
Goyal V
International archives of integrated medicine, 5(3), 30-35 (2015)
The metabolic processes of folic acid and Vitamin B12 deficiency
Mahmood L
Journal of Health Research and Reviews, 1(1), 5-5 (2014)
Johan Frederik Berg Arendt et al.
Journal of the National Cancer Institute, 105(23), 1799-1805 (2013-11-20)
A substantial proportion of patients referred for plasma vitamin B12 (cobalamin [Cbl]) measurement present with high Cbl levels, which have been reported in patients with different cancer types. However, the cancer risk among patients with newly diagnosed high Cbl levels
Christine M Armour et al.
Pediatrics, 132(1), e257-e261 (2013-06-19)
A neonate, who was found to have an elevated C3/C2 ratio and minimally elevated propionylcarnitine on newborn screening, was subsequently identified as having the rare cblF inborn error of vitamin B12 (cobalamin) metabolism. This disorder is characterized by the retention
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