Benfotiamine

Benfotiamine
  • CAS No.:22457-89-2
Other grades of this product :
Benfotiamine Basic information
Product Name:Benfotiamine
Synonyms:benzoylthiamineo-monophosphate;berdi;betivina;benphothiamine;BENFOTAMINE (S-BENZOYLTHIAMINE-O-MONOPHOSPHATE);S-[2]-[(4-Amino-2-methyl-5-pyrimidinyl)methy-[formylamino]-1-[2-phosphonoxy)ethyl]-1-propenyloic ester phenylcarbathionoic acid;Thiobenzoic acid S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl];Thiobenzoic acid S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester
CAS:22457-89-2
MF:C19H23N4O6PS
MW:466.45
EINECS:245-013-4
Product Categories:API;BIOTAMIN;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceutical intermediate;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Sulfur & Selenium Compounds
Mol File:22457-89-2.mol
Benfotiamine Chemical Properties
Melting point 165 C
Boiling point 745.1±70.0 °C(Predicted)
density 1.444±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Aqueous Acid (Slightly), DMSO (Heated, Sonicated)
form Solid
pka1.84±0.10(Predicted)
color White to Off-White
Merck 14,1041
InChIKeyBTNNPSLJPBRMLZ-GHRIWEEISA-N
CAS DataBase Reference22457-89-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36
WGK Germany 2
RTECS DH6910000
MSDS Information
ProviderLanguage
SigmaAldrich English
Benfotiamine Usage And Synthesis
Chemical Propertiescrystals
OriginatorBiotamin,Sankyo
UsesS-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat.
UsesVitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185).
DefinitionChEBI: A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.
Manufacturing Process28.6 g 84% phosphoric acid was heated to temperature about 270°C. After cooling to 100°C 4 g thiamine hydrochloride (vitamin B1 hydrochloride) was added and left at temperature 100°C before an isolation of HCl was ended. After adding of an ice water and acetone, phosphate ester of vitamin B1 was fallen. The precipitate was dissolved in 17 ml 1 N HCl and stood at ambient temperature 7 days for a hydrolysis. Then a solution was with acetone diluted and the mixture was cooled, whereupon vitamin B1 monophosphate hydrochloride was isolated. The solution of 4.3 parts vitamin B1 monophosphate hydrochloride in 16 parts of water was diluted with 11 parts 15% NaOH, 2.1 parts benzoyl chloride was dropwise added with stirring and cooling. The obtained mixture was neutralized, evaporated in vacuum, acidified with concentrated HCl to pH 3.5- 4, whereupon a crude S-derivative of vitamin B1 monophosphate ester was precipitated. The product was suspended in water, was bringing with NaOH to pH 7 and was acidified to pH 4. 3.4 g refined S-benzoylthiamine Omonophosphate was prepared; MP: 165°C (with decomposition).
Therapeutic FunctionAnalgesic
General DescriptionS-Benzoylthiamine O-monophosphate (Benfotiamine) is an amphiphilic S-acyl thiamine derivative. It is a lipid-soluble vitamin. Benfotiamine?contains a thiazole ring. Benfotiamine has a greater bioavailability than thiamine.
Biochem/physiol ActionsS-Benzoylthiamine O-monophosphate (Benfotiamine) is a therapeutic agent. It helps in the prevention of diabetic complications such as, retinopathy, neuropathy and nephropathy. Benfotiamine inhibits the synthesis of glycation end products (AGEs) in diabetes. Benfotiamine is considered as a nutraceutical product for the prevention of diabetic neuropathy.
Benfotiamine Preparation Products And Raw materials
Raw materialsBenzoyl chloride-->Thiamine hydrochloride-->Phosphoric acid

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