43107

Sigma-Aldrich

Cyanocobalamin

tested according to Ph. Eur.

Synonym(s):
Vitamin B12, α-(5,6-Dimethylbenzimidazolyl)cyanocobamide, CN-Cbl, Cyanocob(III)alamin, Cyanocobalamin
Empirical Formula (Hill Notation):
C63H88CoN14O14P
CAS Number:
Molecular Weight:
1355.37
Beilstein/REAXYS Number:
4122889
EC Number:
PubChem Substance ID:
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

biological source

fermentation/recombinant

Agency/Method

USP/NF
tested according to Ph. Eur.

assay

96.0-102.0% dry basis

form

powder

application(s)

cell analysis: suitable

color

dark red

solubility

water: soluble 1 gm in 80 ml
acetone: insoluble
alcohol: soluble
chloroform: insoluble
diethyl ether: insoluble

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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General description

Cyanocobalamin, also referred to as Vitamin B12, is a water soluble vitamin.

Application

Cyanocobalamin was added in the assay buffer during the analysis step of ELISA for ensuring that all transcobalamin was saturated with cobalamin before analysis. Cyanocobalamin was also used for examining its impact on the expression of mPer1 and mPer2 in vivo.

Biochem/physiol Actions

Cyanocobalamin 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. Cyanocobalamin along with other B vitamins thiamine (B1) and pyridoxine (B6) blocks the thermal hyperalgesia in rats with neuropathic pain caused by spinal ganglia compression (CCD) or loose ligation of the sciatic nerve (CCI). It can stimulate the anaerobic biodegradation of chloroform.
Cyanocobalamin plays a role in functioning of brain and nervous system. It is also involved in hematopoiesis. Vitamin B12 deficiency leads to megaloblastic anemia. It is also associated with irreversible nervous system breakdown leading to spinal cord degeneration.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Anti-nociceptive and anti-inflammatory effects of cyanocobalamin (vitamin B12) against acute and chronic pain and inflammation in mice
Hosseinzadeh H, et al.
Arzneimittelforschung, 62(07), 324-329 (2012)
Zheng-Bei Wang et al.
Pain, 114(1-2), 266-277 (2005-03-01)
Neuropathic pain after nerve injury is severe and intractable, and current drugs and nondrug therapies offer substantial pain relief to no more than half of affected patients. The present study investigated the analgesic roles of the B vitamins thiamine (B1)...
E Nexo et al.
Clinical chemistry, 46(10), 1643-1649 (2000-10-06)
Transcobalamin is essential for the cellular internalization of cobalamin. Methods to quantify the unsaturated protein are available, but few attempts have been made to develop methods to quantify the sum of unsaturated and cobalamin saturated transcobalamin. gamma-Globulins from two polyclonal...
Krista Kaasik et al.
Nature, 430(6998), 467-471 (2004-07-23)
The circadian clock is the central timing system that controls numerous physiological processes. In mammals, one such process is haem biosynthesis, which the clock controls through regulation of the rate-limiting enzyme aminolevulinate synthase 1 (Alas1). Several members of the core...
Hung-Chun Yu et al.
American journal of human genetics, 93(3), 506-514 (2013-09-10)
Derivatives of vitamin B12 (cobalamin) are essential cofactors for enzymes required in intermediary metabolism. Defects in cobalamin metabolism lead to disorders characterized by the accumulation of methylmalonic acid and/or homocysteine in blood and urine. The most common inborn error of...

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