ChemicalBook > CAS DataBase List > Coenzyme B12

Coenzyme B12

Product Name
Coenzyme B12
CAS No.
13870-90-1
Chemical Name
Coenzyme B12
Synonyms
COBAMAMIDE;adenosylcobalamin;dibencozide;COENZYME B12;lm176;AdoCbl;COBAMIDE;calomide;funacomide;enzyme B12
CBNumber
CB8433734
Molecular Formula
C72H99CoN18O17P
Formula Weight
1578.6
MOL File
13870-90-1.mol
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Coenzyme B12 Property

storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
pka
3.5(at 25℃)
form 
Solid
color 
Red to Very Dark Red
Water Solubility 
26g/L(24 ºC)
Merck 
13,2476
BRN 
4122932
Stability:
Hygroscopic
InChIKey
WAJLPPDUWGAMTH-NGQUPMDYNA-L
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
RTECS 
GG3800000
F 
8
HS Code 
2936260000
Toxicity
LD50 oral in guinea pig: 5gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C0884
Product name
Coenzyme B12
Purity
≥97.0%
Packaging
25mg
Price
$74.2
Updated
2024/03/01
Sigma-Aldrich
Product number
C0884
Product name
Coenzyme B12
Purity
≥97.0%
Packaging
1g
Price
$820
Updated
2024/03/01
Cayman Chemical
Product number
21571
Product name
Coenzyme B12
Purity
≥95%
Packaging
25mg
Price
$25
Updated
2021/12/16
Cayman Chemical
Product number
21571
Product name
Coenzyme B12
Purity
≥95%
Packaging
50mg
Price
$48
Updated
2021/12/16
Sigma-Aldrich
Product number
C0884
Product name
Coenzyme B12
Purity
≥97.0%
Packaging
100mg
Price
$120
Updated
2024/03/01
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Coenzyme B12 Chemical Properties,Usage,Production

Description

Coenzyme B12 (adenosylcobalamin; AdoCbl; 5'-Deoxyadenosylcobalamin) is a form of vitamin B12. It belongs to the corrinoid group of compounds containing a corrin macrocycle and are produced only by certain bacteria and archaea. It is a cofactor for various enzymes, including mutases, eliminases, aminomutases, and reductases. These enzymes catalyze reactions that generate free radicals through the release of the adenosyl group, allowing usually unreactive molecules to become reactive. Genetic mutations in enzymes synthesizing Coenzyme B12 lead to Coenzyme B12 deficiency and methylmalonic aciduria.

Originator

Actimide,Tobishi

Uses

emulsifying agent

Uses

Coenzyme B12 has been used as a supplement for culturing plasmid variants in in vivo assay of yvrC-lacZ fusions.

Definition

ChEBI: A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12.

Definition

Coenzyme B12 (5'-Deoxy-5'-adenosylcobalamin or Ado-Cbl) is the largest molecule among the B type vitamins. It is an essential cofactor in many biological rearrangement reactions. Coenzyme B12 activates enzymes such as methionine synthase (MetH), methyl-malonyl-CoA mutase (MutAB), and glycerol dehydratase (DhaB). Biologically, coenzyme B12 is one of the two main types of vitamin B12, adenosyl-cobalamin and methyl-cobalamin, and the former is highly preferred for many enzymes, including glycerol and diol dehydratases[1].

Manufacturing Process

Isopropylidine adenosine was converted to the p-toluene sulphonyl (tosyl) ester by reaction with tosyl chlorine solution, following the method of Clark et al. (1951) [J. Chem. Soc. 2952]. Because of its tendency to cyclization, the reagent was used directly it was ready. A reaction flask with separating funnels was set up in such a way that the whole system could be evacuated and filled with pure nitrogen two or three times, to eliminate all oxygen, and reagents could then be added when desired, in the closed system.
The flask contained 700.0 mg hydroxocobalamin in 20 ml of water, one funnel 200.0 mg sodium borohydride in 10 ml of water, and another the crude isopropylidine adenosine tosyl ester made from 500 mg isopropylidine adenosine dissolved in 10 ml of 50% aqueous methanol. On adding the borohydride to the vitamin, the color changed instantly from red to brown, then slowly to a greenish black. After 15 min the isopropylidine adenosine tosyl ester was added, and the colour slowly changed to a red-brown. After 45 min at room temperature air was admitted and the mixture was shaken to reoxidise any remaining reduced vitamin B12. The alkaline solution was neutralized with dilute hydrochloric acid and extracted with phenol carbon tetrachloride 3:1 in small portions till the aqueous layer was nearly colorless. The combined extracts were washed with water, mixed with about ten parts of carbon tetrachloride-acetone 10:1 and shaken with small portions of water till all red color was removed.
The product was purified by chromatography on columns of DEAE (diethyl aminoethyl) cellulose (3 x 1) followed by CM (carboxymethyl) cellulose (6 x 1), developed with water. Nearly all the color washed quickly through DEAE cellulose. The effluent and washes were applied to the CM cellulose column, which was further developed with water. Elution was continued as long as this fraction continued to emerge, in a total of 850 ml. One half of this fraction (425 ml) was concentrated to a few ml under reduced pressure; it crystallized slowly after adding acetone to slight turbidity. So cobamamide was obtained.

Therapeutic Function

Anabolic, Analgesic

Biotechnological Production

There exist two distinctive routes for the biosynthesis of coenzyme B12, namely oxygen-dependent (encoded by cob operons) and oxygen-independent (by CBI operons) pathways. Their requirement of molecular oxygen during synthesis and the point at which cobalt is inserted into the corrin ring. De novo coenzyme B12 biosynthesis is limited to some bacteria and archaea. The aerobic pathway is present in Pseudomonas denitrificans, Sinorhizobium meliloti, Rhodobacter sphaeroides and Pseudomonas aeruginosa. At the same time, the anaerobic one is present in Salmonella typhimurium, Klebsiella pneumoniae, Citrobacter amalonaticus, Bacillus megaterium, Propionibacterium shermanii and Lactobacillus reuteri.

General Description

Vitamin B12 cobalamin refers to a group of chemically-related cobalt containing molecules. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms.

Agricultural Uses

Cobamide enzyme is the cobalt complex formed between the cobalt-porphyrin ring structure and the nucleotide in vitamin B12 co-enzyme.

Biochem/physiol Actions

Vitamin B12 cobalamin is involved in DNA synthesis and fatty acid synthesis. It also plays a vital role as a coenzyme in the conversion of mitochondrial methylmalonyl co-enzyme A to succinyl co-enzyme A.

References

[1] Thuan Phu Nguyen-Vo. “Analysis and characterization of coenzyme B12 biosynthetic gene clusters and improvement of B12 biosynthesis in Pseudomonas denitrificans ATCC 13867.” Fems Microbiology Letters 365 21 (2018).
[2] I. I. Merkelbach, Hm Henk Buck. “Mechanism of action of coenzyme B12. Quantum-chemical considerations.” Recueil des Travaux Chimiques des Pays-Bas 28 1 (2010): 166–169.
[3] Prof. Dr. Karl Gruber, Prof. Dr. Bernhard Krutler. “Coenzyme B12 Repurposed for Photoregulation of Gene Expression.” Angewandte Chemie International Edition 55 19 (2016): 5638–5640.

Coenzyme B12 Preparation Products And Raw materials

Raw materials

Chlortetracycline Sodium cyanide

Preparation Products

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View Lastest Price from Coenzyme B12 manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
Vitamin B12 Cobamamide 13870-90-1
Price
US $150.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500kg
Release date
2024-12-06
WUHAN FORTUNA CHEMICAL CO., LTD
Product
5'-Deoxyadenosylcobalamin 13870-90-1
Price
US $0.00/g
Min. Order
50g
Purity
99%
Supply Ability
10kg/month
Release date
2021-07-20
Hebei Weibang Biotechnology Co., Ltd
Product
5'-Deoxyadenosylcobalamin 13870-90-1
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-22

13870-90-1, Coenzyme B12Related Search:

HYDROXOCOBALAMIN HYDROCHLORIDE Magnesium ascorbyl phosphate Calcium D-Pantothenate Riboflavin Ascorbic Acid Sodium ascorbate 3-O-Ethyl-L-ascorbic acid Pyridoxine hydrochloride Cobalt Adenine Adenosine Diisopropyl phosphite 1,12-Dodecanediamine 2-Methyl-1-pyrroline 5,6-Dimethylbenzimidazole 5'-Deoxyadenosylcobalamin (R)-3,3-DIMETHYL-2-AMINOBUTANE N-(2-hydroxypropyl)dodecanamide Coenzyme B12

  • DIMETHYLBENZIMIDAZOLYLCOBAMIDE COENZYME, 5,6-
  • DMBC COENZYME
  • COENZYME B12
  • COBAMAMIDE
  • COBAMAMIDE/DIBENCOZIDE
  • COBAMIDE
  • 5'-deoxyadenosylcobalamin
  • 5'-DEOXYADENOSYLCOBALAMINE
  • ADENOSYL COBALAMINE
  • 5,6-DIMETHYLBENZIMIDAZOLYLCOBAMIDE COENZYME
  • ster),innersalt,3’-esterwith5,6-dimethyl-1-alpha-d-ribofuranosylbenzimidaz
  • coenzyme B12 crystalline
  • Cobamamide/VitaminB12
  • Coenzyme B<sub>1</sub><sub>2</sub>
  • ADENOSYLCOBALAMINE(COENZYME B12)(RG)
  • COBAMAMIDE (PYROGEN FREE)
  • 5μ-Deoxyadenosylcobalamine, Adenosyl cobalamine, Cobamamide, DMBC coenzyme
  • cobalaminecoenzyme
  • cobinamide,o-(5’-deoxyadenosine-5’)deriv.,hydroxide,dihydrogenphosphate(e
  • dbccoenzyme
  • deoxyadenosylcobalamin
  • dibencozide
  • funacomide
  • lm176
  • ADENOSYLCOBALAMINE(COENZYME B12)(P)
  • Coenzyme B12,5′-Deoxyadenosylcobalamine, Adenosyl cobalamine, Cobamamide, DMBC coenzyme
  • ADENOSYLCOBALAMINE(COENZYME B12)(AS)
  • CobinaMide,Co-(5'-deoxyadenosin-5'-yl)-, f-(dihydrogen phosphate), inner salt, 3'-esterwith (5,6-diMethyl-1-a-D-ribofuranosyl-1H-benziMidazole-kN3) (9CI)
  • Cobamamide (Dibencozide, Coenzyme B12)
  • COENZYME B12, >=97.0%
  • Cyanocobalamin Impurity 14
  • 5’-deoxyadenosylvitaminb12
  • adenosylcobalamin
  • calomide
  • AdoCbl
  • Cobamamide， DMBC coenzyme
  • Cobinamide, Co-(5'-deoxyadenosin-5'-yl)-, f-(dihydrogen phosphate),inner salt, 3'-ester with(5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole-kN3)
  • 5'-Deoxyadenosylcobalamin USP/EP/BP
  • (2S,3S,4R,5R)-2-(6-Aminopurin-9-yl)-5-methanidyloxolane-3,4-diol
  • enzyme B12
  • [(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,4Z,7S,9Z,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] hydrogen phosphate
  • ADENOSYLCOBALAMINE(COENZYME B12)
  • Cobamamide (Active Vitamin B12)
  • Cobamamide|||Coenzyme B12|||AdoCbl
  • 5'-Deoxyadenosylcobalamin
  • Vitamin B12 Cobamamide
  • Cyanocobalamin Impurity K
  • 13870-90-1
  • C72Co1H100N18O17P1
  • C72H100CoN18O17P
  • Other Cofactors
  • Enzymes, Inhibitors, and Substrates
  • Cofactors
  • Biochemicals and Reagents
  • BioChemical
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • PHARMACEUTICALS