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C3021

Sigma-Aldrich

Dicyanocobinamide

≥93%

Synonyme(s) :

Cobinamide dicyanide, Etiocobalamin, Factor B

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About This Item

Formule empirique (notation de Hill):
C50H72CoN13O8
Numéro CAS:
27792-36-5
Poids moléculaire :
1042.12
Numéro MDL:
MFCD00056330
Code UNSPSC :
12352205
ID de substance PubChem :
24892558
Nomenclature NACRES :
NA.79

Source biologique

synthetic (organic)

Niveau de qualité

200

Pureté

≥93%

Forme

powder

Impuretés

≤0.1% vitamin B12

Couleur

purple to very dark purple

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

NJATWHPHZUGTHR-GXEWULDJSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Koustav Ganguly et al.
Particle and fibre toxicology, 14(1), 19-19 (2017-06-24)
The death toll associated with inhaled ambient particulate matter (PM) is attributed mainly to cardio-vascular rather than pulmonary effects. However, it is unclear whether the key event for cardiovascular impairment is particle translocation from lung to circulation (direct effect) or
Mounia Kortebi et al.
PLoS pathogens, 13(11), e1006734-e1006734 (2017-12-01)
Listeria monocytogenes causes listeriosis, a foodborne disease that poses serious risks to fetuses, newborns and immunocompromised adults. This intracellular bacterial pathogen proliferates in the host cytosol and exploits the host actin polymerization machinery to spread from cell-to-cell and disseminate in
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
Ajitanuj Rattan et al.
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
Conformational change of a tryptophan residue in BtuF facilitates binding and transport of cobinamide by the vitamin B12 transporter BtuCD-F
Mireku SA, et al.
Scientific reports, 7, 41575-41575 (2017)
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