V2876 Sigma-Aldrich

Vitamin B12


Synonym: α-(5,6-Dimethylbenzimidazolyl)cyanocobamide, CN-Cbl, Cyanocob(III)alamin, Cyanocobalamin

  • CAS Number 68-19-9

  • Empirical Formula (Hill Notation) C63H88CoN14O14P

  • Molecular Weight 1355.37

  •  Beilstein/REAXYS Number 4122889

  •  EC Number 200-680-0

  •  eCl@ss 34058004

  •  PubChem Substance ID 57654727

  •  NACRES NA.79



Related Categories Biochemicals and Reagents, Cell Biology, Cofactors, Enzymes, Inhibitors, and Substrates, Nutrition Research,
Quality Level   200
biological source   synthetic (organic)
assay   ≥98%
form   powder
application(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



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)


1, 5, 25 g in glass bottle

100, 250, 500 mg in glass bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
How should I store a solution of Vitamin B12, Product V2876?
Serum Vitamin B12 is highly unstable andshould be protected from light and kept frozen. Cyanocobalamin is often used to supplement media. It has a maximal stability at pH = 7, but is photolysed to hydroxocobalamin with a zero-order rate constant.
Vitamin B12, Product V2876, is produced by fermentation.What bacteria is used to produce this product?
The bacterial source for this product is considered proprietary.
What can I use to make a solution of Vitamin B12, Product V2876?
The specification sheet for Product V2876 (available from the product page on the website) indicates that the product is soluble in water (50 mg/mL), yielding a dark red solution.
What is the Extinction Coefficient for Vitamin B12, Product V2876?
Extinction Coefficient: E1% = 64 (550 nm), 204 (361 nm), 115 (278 nm) in water.Extinction Coefficient: EmM = 27.5 (361 nm) in water.
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Protocols & Articles


MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers


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