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V2876

Sigma-Aldrich

Vitamin B12

≥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:
Molecular Weight:
1355.37
Beilstein:
4122889
EC Number:
eCl@ss:
34058004
PubChem Substance ID:
NACRES:
NA.79

Quality Level

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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This Item
C360743107C3000000
Vitamin B12 ≥98%

Sigma-Aldrich

V2876

Vitamin B12

Cyanocobalamin meets USP testing specifications

Sigma-Aldrich

C3607

Cyanocobalamin

Cyanocobalamin tested according to Ph. Eur.

Sigma-Aldrich

43107

Cyanocobalamin

Cyanocobalamin European Pharmacopoeia (EP) Reference Standard

C3000000

Cyanocobalamin

assay

≥98%

assay

96.0-102.0% dry basis

assay

96.0-102.0% dry basis

assay

-

form

powder

form

powder

form

powder

form

solid

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

-

technique(s)

gas chromatography (GC): suitable, liquid chromatography (LC): suitable

color

red to brown

color

dark red

color

dark red

color

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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 Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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25G
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Cyanocobalamin European Pharmacopoeia (EP) Reference Standard

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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)
Raman spectroscopic analysis of high molecular weight proteins in solution-considerations for sample analysis and data pre-processing
Parachalil DR, et al.
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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
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