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Merck

M9756

Sigma-Aldrich

Methylcobalamin

vitamin B12 analog

Sinónimos:

Methyl cobalamine

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About This Item

Fórmula empírica (notación de Hill):
C63H91CoN13O14P
Número de CAS:
Peso molecular:
1344.38
EC Number:
MDL number:
UNSPSC Code:
12352205
eCl@ss:
34058004
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

assay

≥97%

form

powder

technique(s)

HPLC: suitable

color

red to very dark red

storage temp.

−20°C

SMILES string

C[Co+]N1C2=C(C)C3=NC(=CC4=NC([C@@H](CCC(N)=O)C4(C)C)=C(C)C5=N[C@H]([C@H](CC(N)=O)[C@@]5(C)CCC(=O)NCC(C)OP([O-])(=O)O[C@H]6[C@@H](O)[C@H](O[C@@H]6CO)n7cnc8cc(C)c(C)cc78)[C@@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O)[C@@H](CCC(N)=O)[C@]3(C)CC(N)=O

InChI

1S/C62H90N13O14P.CH3.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;;/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);1H3;/q;;+2/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1

InChI key

JEWJRMKHSMTXPP-WYVZQNDMSA-L

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General description

Methylcobalamin (MeCbl) is an analog of vitamin B12 (cobalamin). It differs from cobalamin by containing a methyl group. The physiologically active form of vitamin B12 include methylcobalamin and adenosylcobalamin.

Application

Methylcobalamin has been used for the preparation of standard solution to serum vitamin B12 in automated competitive protein binding (CPB) assays.

Biochem/physiol Actions

Methylcobalamin (MeCbl) is a coenzyme for methionine synthase. Methionine synthase is an enzyme, that is involved in the conversion of homocysteine to methionine in the methylation cycle. It plays a role in nervous disorder improvement, carpal tunnel syndrome and bell′s palsy.
Vitamin B12 analog that is a less effective inhibitor of nitric oxide synthase (NOS) than other corrins/cobalamin derivatives.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Methylcobalamin increases Erk1/2 and Akt activities through the methylation cycle and promotes nerve regeneration in a rat sciatic nerve injury model
Okada K, et al.
Experimental Neurology, 222(2), 191-203 (2010)
Neeraj Kumar et al.
Inorganic chemistry, 52(4), 1762-1771 (2013-01-31)
The electronic and structural properties of the one-electron-oxidized form of methylcobalamin (MeCbl) cofactor have been investigated using density functional theory (DFT) and CASSCF/MC-XQDPT2 calculations. We applied two types of functionals (hybrid and GGA) which produced quite different results in terms
Hyoung-Il Kim et al.
Annals of surgical oncology, 18(13), 3711-3717 (2011-05-11)
Vitamin B12 deficiency is a common long-term sequelae after total gastrectomy. Intramuscular injection of vitamin B12 is the only known treatment. We investigated the efficacy and safety of oral vitamin B12 replacement for gastric cancer patients with vitamin B12 deficiency
Hajime Hirao
The journal of physical chemistry. A, 115(33), 9308-9313 (2011-08-03)
Controversy remains regarding the suitable density functionals for the calculation of vitamin B(12) systems that contain cobalt. To identify the optimum functionals, geometry optimization calculations were performed on a full-size model of methylcobalamin (MeCbl) using the B3LYP, B3LYP-D, BP86, and
David Watkins et al.
American journal of medical genetics. Part C, Seminars in medical genetics, 157C(1), 33-44 (2011-02-12)
Derivatives of cobalamin (vitamin B(12)) are required for activity of two enzymes in humans. Adenosylcobalamin is required for activity of mitochondrial methylmalonylCoA mutase and methylcobalamin is required for activity of cytoplasmic methionine synthase. Deficiency in cobalamin, or inability to absorb

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