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MilliporeSigma

M9756

Methylcobalamin

vitamin B12 analog

Synonym(s):

Methyl cobalamine

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$162.00

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About This Item

Empirical Formula (Hill Notation):
C63H91CoN13O14P
CAS Number:
13422-55-4
Molecular Weight:
1344.38
PubChem Substance ID:
329818096
eCl@ss:
34058004
UNSPSC Code:
12352205
NACRES:
NA.79
EC Number:
236-535-3
MDL number:
MFCD00082483

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Product Name

Methylcobalamin, vitamin B12 analog

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

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

assay

≥97%

form

powder

technique(s)

HPLC: suitable

color

red to very dark red

storage temp.

−20°C

Quality Level

100

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1 of 4

This Item
1424550PHR3410C0884
Methylcobalamin vitamin B12 analog

Sigma-Aldrich

M9756

Methylcobalamin

Methylcobalamin United States Pharmacopeia (USP) Reference Standard

USP

1424550

Methylcobalamin

Methylcobalamin certified reference material, pharmaceutical secondary standard

Supelco

PHR3410

Methylcobalamin

Coenzyme B12 ≥97.0%

Sigma-Aldrich

C0884

Coenzyme B12

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

-

technique(s)

HPLC: suitable

assay

≥97%

assay

-

assay

-

assay

≥97.0%

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

-

form

powder

form

-

form

-

form

powder and chunks

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

Quality Level

100

Quality Level

-

Quality Level

300

Quality Level

100

Application

Methylcobalamin has been used for the preparation of standard solution to serum vitamin B12 in automated competitive protein binding (CPB) assays.[1]

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.[2] It plays a role in nervous disorder improvement, carpal tunnel syndrome and bell′s palsy.[2]
Vitamin B12 analog that is a less effective inhibitor of nitric oxide synthase (NOS) than other corrins/cobalamin derivatives.[3]

General description

Methylcobalamin (MeCbl) is an analog of vitamin B12 (cobalamin). It differs from cobalamin by containing a methyl group.[2][4] The physiologically active form of vitamin B12 include methylcobalamin and adenosylcobalamin.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD3477
MKBQ8648V
SLBF1697V
SLBF1697
SLBD8698

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Kiyoshi Okada et al.
Neuroscience letters, 495(3), 201-204 (2011-04-05)
Methylcobalamin (MeCbl), a vitamin B12 analog, promotes neurite outgrowth by activating Akt in neurons. However, Akt is involved in many cellular functions, and the downstream signal of Akt that promotes neurite outgrowth in neurons in the presence of MeCbl remains
C L Drennan et al.
Current opinion in structural biology, 4(6), 919-929 (1994-12-01)
Cobalamin-dependent methionine synthase is a large enzyme composed of structurally and functionally distinct regions. Recent studies have begun to define the roles of several regions of the protein. In particular, the structure of a 27 kDa cobalamin-binding fragment of the
Methylcobalamin: a potential vitamin of pain killer
Zhang M, et al.
Neural Plast. (2013)
John David Spence
Clinical chemistry and laboratory medicine, 51(3), 633-637 (2013-03-02)
Therapy to lower homocysteine with B vitamins does reduce the risk of stroke, if not myocardial infarction. The apparent lack of efficacy of vitamin therapy in most of the large clinical trials was probably determined by the failure to take
Kenneth M Prentice et al.
mAbs, 5(6), 974-981 (2013-08-09)
Process control of protein therapeutic manufacturing is central to ensuring the product is both safe and efficacious for patients. In this work, we investigate the cause of pink color variability in development lots of monoclonal antibody (mAb) and Fc-fusion proteins.
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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