22457-89-2 Usage
Description
Benfotiamine, also known as S-Benzoylthiamine O-monophosphate, is an amphiphilic S-acyl thiamine derivative and a lipid-soluble vitamin. It is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phosphorylation. Benfotiamine contains a thiazole ring and has a greater bioavailability than thiamine. It is available in the form of crystals.
Uses
Used in Pharmaceutical Industry:
Benfotiamine is used as a Vitamin B1 analog for its potential therapeutic effects on various health conditions. As a synthetic S-acyl derivative of Thiamine, it offers enhanced bioavailability compared to traditional thiamine, making it a valuable compound in the development of pharmaceutical products.
Used in Research Applications:
In research settings, Benfotiamine is used to study its effects on ischemia and reperfusion in skeletal muscles of rats. This helps in understanding the compound's potential applications in treating conditions related to blood flow and muscle health.
Used in Nutritional Supplements:
Due to its enhanced bioavailability and status as a Vitamin B1 analog, Benfotiamine is also used in the development of nutritional supplements aimed at supporting overall health and well-being.
Originator
Biotamin,Sankyo
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 22457-89-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,4,5 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 22457-89:
(7*2)+(6*2)+(5*4)+(4*5)+(3*7)+(2*8)+(1*9)=112
112 % 10 = 2
So 22457-89-2 is a valid CAS Registry Number.
InChI:InChI=1/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)/b17-13+
22457-89-2Relevant articles and documents
Benfotiamine related substance as well as preparation method, application and detection method thereof
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Paragraph 0027-0029, (2021/05/12)
The invention discloses a benfotiamine related substance as well as a preparation method, application and a detection method thereof. The benfotiamine related substance is a compound H, and the structure of the compound H is shown in the description. The preparation method provided by the invention is simple, and the compound H with the purity meeting the requirement can be prepared. The invention also provides a detection method of the benfotiamine related substance. The high-purity compound H can be used as a benfotiamine reference substance or standard substance, and has a good application prospect.
A method for the production of thiamine benzene phosphorus
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Paragraph 0032; 0034, (2017/01/12)
The invention relates to a production method of benfotiamine. The production method comprises the following steps: by taking polyphosphoric acid as a phosphoric acid esterification reagent, reacting with vitamin B1, performing hydrolysis at high temperature after the end of reaction, extracting phosphoric acid of a system by using a mixed solution of trioctylamine and an organic solvent after the end of hydrolysis, and then directly adding the organic solvent to precipitate a phosphate monoester crude product of vitamin B1. The obtained crude product is not purified, water is directly used for pulping, the pH value is adjusted by using liquid alkali, the reaction is performed with benzoyl chloride, and solids are filtered. The pH value of filtrate is adjusted to 3.5-4.0, the solids are precipitated, and separation and drying are performed to obtain the white solids, namely benfotiamine. The yield of benfotiamine produced by using the process is high, the product purity is high, the operation is simple, and the production method is environment-friendly and suitable for industrial production.
BENFOTIAMINE POLYMORPHS, PREPARATION METHOD AND USE THEREOF
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Paragraph 0044; 0045, (2015/11/09)
The present invention is directed to polymorphs of benfotiamine, their methods of preparation and the use thereof. The crystalline forms of benfotiamine are crystalline forms A, B, C, D and E, and can be distinguished by their respective patterns of X-ray powder diffraction, DSC, infrared spectroscopy, Raman spectroscopy, and preparation methods. The invention is also directed to the use of the above-mentioned polymorphs of benfotiamine for treating Vitamin B1 deficiency, metabolism-related disorders, psychiatric diseases and disorders, diabetes complications, or neurodegenerative diseases. The different crystalline forms of benfotiamine are obtained using different synthetic routes and solvent ratios. The crystalline polymorphs are substantially pure. The invention not only provides new crystalline forms of benfotiamine, but also solvates thereof, especially hydrates.