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

pka

1.84±0.10(Predicted)

color 

White to Off-White

Merck 

14,1041

Stability:

Hygroscopic

InChI

InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)

InChIKey

BTNNPSLJPBRMLZ-GHRIWEEISA-N

SMILES

C(C1=CN=C(C)N=C1N)N(C=O)C(C)=C(CCOP(O)(O)=O)SC(C1C=CC=CC=1)=O

LogP

-2.814 (est)

CAS DataBase Reference

22457-89-2(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

HS Code 

2933.59.8000

MSDS

• Language:English Provider:SigmaAldrich

Benfotiamine Usage And Synthesis

Chemical Properties

crystals

Originator

Biotamin,Sankyo

Uses

S-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat.

Uses

Vitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185).

Definition

ChEBI: A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.

Manufacturing Process

28.6 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 Function

Analgesic

General Description

S-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 Actions

S-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.

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