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V6629

Sigma-Aldrich

Vitamin B12

BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, ≥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:
Molecular Weight:
1355.37
Beilstein/REAXYS Number:
4122889
EC Number:
UNSPSC Code:
12352205
eCl@ss:
34058004
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic ((organic))

product line

BioReagent

assay

≥98%

form

powder

mol wt

Mw 1355.37 g/mol

technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable
cell culture | plant: suitable

color

red to brown

pH

6

solubility

water: soluble 50 mg/mL, dark red

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

Cyanocobalamin (B12) is a water soluble vitamin, commonly called as cobalamins. Dairy products, meat and eggs are the major sources of this vitamin.

Application

Vitamin B12 has been used:
  • as a component of Erdschreiber′s medium
  • as a supplement of Dulbecco′s modified Eagle′s medium used for the isolation of ventricular myocytes from neonatal and adult rats
  • orally administered to male quails to study its role in reducing the negative effects of sodium selenite intoxication, in vivo
  • as a supplement in DMEM/ medium 199 (M199) medium for differentiation of human myoblasts.

Biochem/physiol Actions

Vitamin B12 is metabolized to its active form, methylcobalamin. Hindered vitamin B12 uptake is observed in pernicious anemia. Vitamin B12 is essential for erythroblast development. Pregnancy reduces the levels of vitamin B12. Aging reduces vitamin B12 absorption. It works as a coenzyme in fat, carbohydrate and protein metabolism. It is required for growth, genetic stability and survival of cells in vitro. Functions to support one-carbon metabolism. Present in many classical and serum-free formulations.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Selenium toxicosis assessment (in vivo and in vitro) and the protective role of vitamin B12 in male quail (Coturnix coturnix)
Gad MA and El-Twab SMA
Environmental Toxicology and Pharmacology, 27(1), 7-16 (2009)
miRNA-204 drives cardiomyocyte proliferation via targeting Jarid2
Liang D, et al.
International Journal of Cardiology, 201, 38-48 (2015)
Vitamins, minerals and trace elements
Drugs During Pregnancy and Lactation (2015)
Toward Ameliorating Insulin Resistance: Targeting a Novel PAK1 Signaling Pathway Required for Skeletal Muscle Mitochondrial Function
Balakrishnan R, et al.
Antioxidants, 12(9), 1658-1658 (2023)
Vitamins for chronic disease prevention in adults: clinical applications
Fletcher RH and Fairfield KM
JAMA : The Journal of the American Medical Association, 287(23), 3127-3129 (2002)

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