| Identification | More | [Name]
Benfotiamine | [CAS]
22457-89-2 | [Synonyms]
n-((4-amino-2-methyl-5-pyrimidinyl)methyl)-n-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide-s-benzoate dihydrogen phosphate
S-BENZOYLTHIAMINE O-MONOPHOSPHATE
(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamidedihydrogenphosphate(ester
8088c.b.
benzoylthiaminemonophosphate
benzoylthiamineo-monophosphate
berdi
betivina
bietamine
biotamin
btmp
neurostop
nitanevril
s-benzoylthiaminemonophosphate
s-esterwithn-((4-amino-2-methyl-5-pyrimidinyl)methyl)-n-benzoicaci
tabiomyl
thiaminemonophosphatebenzoyl
vitanevril
benphothiamine
N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide-S-benzoate dihydrogen phosphate | [EINECS(EC#)]
245-013-4 | [Molecular Formula]
C19H23N4O6PS | [MDL Number]
MFCD00057343 | [Molecular Weight]
466.45 | [MOL File]
22457-89-2.mol |
| Chemical Properties | Back Directory | [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 | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
DH6910000
| [HS Code ]
2933.59.8000 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
crystals | [Originator]
Biotamin,Sankyo | [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. | [Synthesis]
Benfotiamine was synthesized starting from thiamine chloride hydrochloride via the key intermediate thiamine monophosphate[1]. Crude benfotiamine was purified and crystallized using methanol and sodium dithionite, or recrystallized from various solvents such as methanol and tert-amyl alcohol to yield pure crystalline forms[1]. | [References]
[1]Hanganu, A., Maximov, M., Maximov, O.-C., Popescu, C. C., Sandu, N., Florea, M., Mirea, A. G., Gârbea, C., Matache, M., & Funeriu, D. P. (2024). Insights into Large-Scale Synthesis of Benfotiamine. Organic Process Research & Development, 28(11), 4069–4078. https://doi.org/10.1021/acs.oprd.4c00351 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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