Coenzyme B12

ChemicalBook > CAS DataBase List > 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 B_12a, 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 B₁₂co-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

Shaanxi TNJONE Pharmaceutical Co., Ltd

Product: Cobamamide 13870-90-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20tons
Release date: 2024-04-29

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

Henan Bao Enluo International TradeCo.，LTD

Product: 5'-Deoxyadenosylcobalamin 13870-90-1
Price: US $100.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000tons
Release date: 2023-08-03

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

Cyanocobalamin Impurity K

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)

13870-90-1

C72Co1H100N18O17P1

C72H100CoN18O17P

Other Cofactors

Enzymes, Inhibitors, and Substrates

Cofactors

Biochemicals and Reagents

BioChemical

Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts

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