All Photos(2)

C3021

Sigma-Aldrich

Dicyanocobinamide

≥93%

Synonym(s):
Cobinamide dicyanide, Etiocobalamin, Factor B
Empirical Formula (Hill Notation):
C50H72CoN13O8
CAS Number:
Molecular Weight:
1042.12
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic (organic)

assay

≥93%

form

powder

impurities

≤0.1% vitamin B12

color

purple to very dark purple

storage temp.

−20°C

SMILES string

N#C[Co]C#N.C[C@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N=C1C(C)=C3N=C(C=C4N=C(C(C)=C5N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O

InChI

1S/C48H73N11O8.2CN.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;2*1-2;/h19,23,26-29,43,59-60H,10-18,20-22H2,1-9H3,(H2,49,61)(H2,50,62)(H2,51,63)(H2,52,64)(H2,53,65)(H2,54,66)(H,55,67);;;/b30-19-,39-24-,40-25-;;;/t23-,26+,27+,28+,29-,43?,45+,46-,47-,48-;;;/m0.../s1

InChI key

NJATWHPHZUGTHR-GXEWULDJSA-N

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General description

Dicyanocobinamide, also known as factor b is a coenzyme B12 precursor. It has a corrin ring structure with four of the six coordination sites of the cobalt (Co) atom being the pyrrole nitrogen atoms.

Application

Dicyanocobinamide has been used for the crystallization of vitamin B12-binding protein (BtuF). It has also been used for the destabilization of BtuCD-BtuF Interaction.
For use in determining non-intrinsic factor (R protein) in intrinsic factor preparations.

Packaging

10, 50 mg in glass bottle

Biochem/physiol Actions

Dicyanocobinamide (Cbi) functions as a soluble guanylate cyclase (sGC) co-activator and targets the N-terminal regulatory regions. This action is similar to the effect of forskolin on adenylyl cyclases. Dicyanocobinamide elevates the intracellular cyclic guanosine monophosphate (cGMP) levels and exhibits vasorelaxant activity in rats. It is used along with various cobalamins in studies of the inhibition of HIV-1 integrase and nitric oxide synthase.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

More documents

Quotes and Ordering

Longxing Cao et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(47), 13438-13443 (2016-11-09)
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Inhibition of nitric oxide synthase by cobalamins and cobinamides
Weinberg JB, et al.
Free Radical Biology & Medicine, 46(12), 1626-1632 (2009)
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PLoS pathogens, 13(3), e1006248-e1006248 (2017-03-17)
The pandemic influenza A(H1N1) 2009 virus caused significant morbidity and mortality worldwide thus necessitating the need to understand the host factors that influence its control. Previously, the complement system has been shown to provide protection during the seasonal influenza virus
Rebecca L McCullough et al.
American journal of physiology. Gastrointestinal and liver physiology, 315(1), G66-G79 (2018-03-31)
Complement plays a crucial role in microbial defense and clearance of apoptotic cells. Emerging evidence suggests complement is an important contributor to alcoholic liver disease. While complement component 1, Q subcomponent (C1q)-dependent complement activation contributes to ethanol-induced liver injury, the

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