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V2876

Sigma-Aldrich

Vitamin B12

≥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:
68-19-9
Molecular Weight:
1355.37
Beilstein:
4122889
EC Number:
200-680-0
UNSPSC Code:
12352205
eCl@ss:
34058004
PubChem Substance ID:
57654727
NACRES:
NA.79
Pricing and availability is not currently available.

Quality Level

200

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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Application

Vitamin B12 has been used:
  • as a constituent in vitamin mix solution in in vitro gut simulator[1]
  • as a standard in size exclusion inductively coupled plasma mass spectroscopy (SEC-ICP-MS)[2]
  • as a constituent of simulated plasma protein mixture for Raman spectra analysis[3]
  • in surface plasmon resonance (SPR) analysis[4]
  • as a medium supplement in neonatal rat ventricular myocytes (NRVM)[5]

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000406579
0000406573
MKCW1046
0000406579
0000406573

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Raman spectroscopic analysis of high molecular weight proteins in solution-considerations for sample analysis and data pre-processing
Parachalil DR, et al.
Analyst, 143(24), 5987-5998 (2018)
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)
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)
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
Silva MS, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1104, 262-268 (2018)
Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1
Koh A, et al.
Cell, 175(4), 947-961 (2018)
View All Related Papers

Questions

1–9 of 9 Questions  

  1. 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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  2. 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/449/386/product-dating-information-mk.pdf

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  3. how long we can store aqueous solution of Vitamin B12 (2876)?

    1 answer

    1. The stability of this product in aqueous solution has not been investigated. It would be up to the end user to determine solution storage and stability. As a conservative measure, it would be recommended to prepare solutions fresh, as needed. However, sterile solutions for injection are available for theratpeutic use and appear to be stable at ambient temperature. These solutions tend to have a pH range from neutral to acidic and are stored in amber bottles. See the link below to review more information on the therapeutic versions of Vitamin B12/Cyanocolamain for injection. https://www.drugs.com/pro/b-2-inject-kit.html

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  4. Is it possible to use ethanol to make a solution of Vitamin B12, Product V2876? May i know the right concentration?

    1 answer

    1. This product is soluble in 50 mg/ml of H2O as stated on the Certificate of Analysis. The solubility of the product in ethanol has not been tested.

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  5. What can I use to make a solution of Vitamin B12, Product V2876?

    1 answer

    1. 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.

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  6. What is the Extinction Coefficient for Vitamin B12, Product V2876?

    1 answer

    1. 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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  7. Vitamin B12, Product V2876, is produced by fermentation.  What bacteria is used to produce this product?

    1 answer

    1. The bacterial source for this product is considered proprietary.

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  8. How should I store a solution of Vitamin B12, Product V2876?

    1 answer

    1. Serum Vitamin B12 is highly unstable and should 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.

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  9. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

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