S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate

Base Information

• Chemical Name: S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
• CAS No.: 22457-89-2
• Molecular Formula: C19H23N4O6PS
• Molecular Weight: 466.455
• European Community (EC) Number: 245-013-4
• ChEMBL ID: CHEMBL1491875
• NCI Thesaurus Code: C169805
• Nikkaji Number: J3.153D
• NSC Number: 758241
• Wikipedia: Benfotiamine
• Mol file: 22457-89-2.mol

Synonyms:benfothiamine;benfotiamine;benphothiamine;BTMP-benfo;milgamma;Neurostop;S-benzoylthiamine monophosphate

Chemical Property of S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.55E-23mmHg at 25°C
• Melting Point: 165 °C
• Refractive Index: 1.645
• Boiling Point: 745.1 °C at 760 mmHg
• PKA: 1.84±0.10(Predicted)
• Flash Point: 404.4 °C
• PSA: 191.05000
• Density: 1.444 g/cm³
• LogP: 3.84720
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), DMSO (Heated, Sonicated)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 466.10759264
• Heavy Atom Count: 31
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Benfotiamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCOP(=O)(O)O)SC(=O)C2=CC=CC=C2)C
• Isomeric SMILES: CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(\CCOP(=O)(O)O)/SC(=O)C2=CC=CC=C2)/C
• Recent ClinicalTrials: A Trial to Evaluate the Safety and Efficacy of Benfotiamine in Patients With Early Alzheimer's Disease (BenfoTeam)
• Recent EU Clinical Trials: Randomized double-blind, placebo-controlled parallel group study over 12 months to assess the effects of treatment with benfotiamine on morphometric, neurophysiological, and clinical measures in type 2 diabetes patients with mild to moderate symptomatic polyneuropathy - BOND Study
• Uses: S-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat. Vitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185).
• Therapeutic Function: Analgesic

Technology Process of S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate

There total 8 articles about S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

thiamine monophosphate chloride (532-40-1) + benzoyl chloride (98-88-4) → S-[2-[[(4-amino-2-methyl-5 pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester (22457-89-2)

Guidance literature:

thiamine monophosphate chloride; With water; sodium hydroxide; at 0 - 15 ℃; for 1h; pH=12.5 - 13;

benzoyl chloride; at -1 - 6 ℃;

With hydrogenchloride; at 0 - 10 ℃; for 3h; pH=3.8 - 4.1;

Reference yield:

→ benfotiamine (22457-89-2)

Guidance literature:

Thiamin-phosphat*HCl in wss. NaOH bei pH=10, Na-Benzoyl-thiosulfat;

Reference yield:

2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate (10023-48-0) + benzoyl chloride (98-88-4) → S-[2-[[(4-amino-2-methyl-5 pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester (22457-89-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 3h;

upstream raw materials:

2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate

benzoyl chloride

vitamin B₁

Thiamine hydrochloride

Refernces

• 1、 -. "Benfotiamine related substance as well as preparation method, application and detection method thereof". Paragraph 0027-0029. . Retrieved 2021/05/12.
• 2、 -. "A Thiamin benzene phosphorus compound and its preparation and its pharmaceutical compositions containing the compounds". Paragraph 0065-0071. . Retrieved 2017/03/08.