3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium

Base Information

• Chemical Name: 3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium
• CAS No.: 70-16-6
• Molecular Formula: C12H17 N4 O S
• Molecular Weight: 265.359
• Hs Code.: 2936220000
• European Community (EC) Number: 200-425-3
• UNII: 4ABT0J945J
• DSSTox Substance ID: DTXSID50220251
• Nikkaji Number: J209.352I
• Wikipedia: Thiamine
• Wikidata: Q83187
• NCI Thesaurus Code: C874
• RXCUI: 1546268
• Metabolomics Workbench ID: 37152
• ChEMBL ID: CHEMBL1547
• Mol file: 70-16-6.mol

Synonyms:Aneurin;Mononitrate, Thiamine;Thiamin;Thiamine;Thiamine Mononitrate;Vitamin B 1;Vitamin B1

Chemical Property of 3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium

Chemical Property:

• Melting Point: 250 °C (dec.)(lit.)
• PSA: 104.15000
• LogP: 1.18890
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.1 g/mL at 20 °C, clear, colorless
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 265.11230735
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
• Recent ClinicalTrials: Impact of Thiamine Supplementation on Mortality in Septic Shock. A Controlled Before-and-after Study.
• Recent EU Clinical Trials: PBC induced fatigue treated with thiamine
• Physical properties: Free thiamin is unstable because of its quaternary nitrogen; in water, it is cleaved to the thiol form. For this reason, the hydrochloride and mononitrate forms are used in commerce. Thiamin hydrochloride (actually, thiamin chloride hydrochloride) is a colorless crystal that is very soluble in water (1 g/ml, thus making it a very suitable form for parenteral administration), soluble in methanol and glycerol, but practi cally insoluble in acetone, ether, chloroform, and benzene. The mononitrate form is more stable than the hydrochloride form, but it is less soluble in water. It is used in food/feed supplementation and in dry pharmaceutical preparations. Free thiamin is easily oxidized to thiamin disulfide and other derivatives, including thiochrome, a yellow biologically inactive product with strong blue fluorescence that can be used for the quantitative determination of thiamin. Its metabolically active form is thia min diphosphate, also called thiamin pyrophosphate.

Technology Process of 3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium

There total 2 articles about 3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium 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:

lactylthiamin (82205-83-2,110223-77-3,110223-78-4) → Aneurin (70-16-6) + 2-oxo-propionic acid (127-17-3)

Guidance literature:

With sodium carbonate; In water; at 25 ℃; Rate constant; deuterium isotope effect;

DOI:10.1021/ja00284a056

Reference yield:

l-cysteine hydrochloride (52-89-1) + water (7732-18-5) + N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-1-methyl-2-methyldisulfanyl-but-1-en-t-yl)-formamide (2281-20-1) + acetic acid (64-19-7,77671-22-8) → S-(methylthio)-L-cysteine (33784-54-2) + Aneurin (70-16-6)

Guidance literature:

bei pH 6.5;

Reference yield: 75.0%

Aneurin (70-16-6) → thiamine pyrophosphate (136-09-4)

Guidance literature:

With thiamin pyrophosphokinase; ATP; magnesium chloride; In water; at 20 ℃; for 12h; pH=8;

DOI:10.1016/j.bmcl.2003.07.026

upstream raw materials:

lactylthiamin

l-cysteine hydrochloride

water

N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-1-methyl-2-methyldisulfanyl-but-1-en-t-yl)-formamide

Downstream raw materials:

N-(2-methyl-4-amino-5-pyrimidinyl)methylaniline

(4-amino-2-methylpyrimidin-5-yl)methanesulfonic acid

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione

oxythiamine chloride hydrochloride

Refernces