Thiamine chloride

Base Information

• Chemical Name: Thiamine chloride
• CAS No.: 59-43-8
• Deprecated CAS: 100660-17-1,115461-66-0,55463-15-5,57777-32-9,115461-66-0,57777-32-9
• Molecular Formula: C12H17ClN4OS
• Molecular Weight: 337.273
• Hs Code.: 3004500000
• European Community (EC) Number: 200-425-3
• UNII: X66NSO3N35
• DSSTox Substance ID: DTXSID2023648
• Wikipedia: Thiamine
• Wikidata: Q27115611
• NCI Thesaurus Code: C874
• RXCUI: 10454
• ChEMBL ID: CHEMBL1588
• Mol file: 59-43-8.mol

Synonyms:VB1;Thiamine(8CI);Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (9CI);Aneurine;Apatate Drape;Beivon;Bethiamin;Oryzanin;Thiacoat;Thiamin;Thiamine monochloride;Vitamin B1;Vitaneurin;thiamine;3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride;

Chemical Property of Thiamine chloride

Chemical Property:

• Appearance/Colour: white fine powder
• Melting Point: 125 °C
• Refractive Index: 1.5630 (estimate)
• PSA: 104.15000
• Density: 6 g/cm3
• LogP: -1.80710
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 300.0811600
• Heavy Atom Count: 19
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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.[Cl-]
• Recent ClinicalTrials: Efficacy of Early Intravenous High-dose Vitamin C in Post-cardiac Arrest Shock.
• Recent EU Clinical Trials: PBC induced fatigue treated with thiamine
• General Description: Thiamine chloride, also known as vitamin B1 or thiamine, is an essential nutrient involved in metabolic processes as a cofactor for thiamine diphosphate-dependent enzymes such as transketolase (TK). While hydroxythiamine (HT) acts as a potent vitamin B1 antagonist by inhibiting these enzymes in most tissues, it cannot cross the blood-brain barrier, limiting its effects on the brain. Modified HT esters have been developed to retain HT’s inhibitory properties while enabling penetration into nerve tissue, resulting in milder systemic effects but enhanced activity in the brain. These findings highlight the potential of such derivatives as targeted vitamin B1 antagonists with improved neurological action.

Technology Process of Thiamine chloride

There total 13 articles about Thiamine chloride 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 hydrochloride (67-03-8,70732-86-4) → vitamin B1 (59-43-8)

Guidance literature:

With sodium hydroxide; In ethanol;

DOI:10.1055/s-1986-31879

Reference yield:

2-(α-hydroxybenzyl)thiaminium chloride (27350-85-2,134876-54-3) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + vitamin B1 (59-43-8) + benzaldehyde (100-52-7)

Guidance literature:

With potassium hydroxide; oxygen; In methanol; Mechanism; and under aerobic conditions;

Reference yield:

thiamine diphosphate (154-87-0) → vitamin B1 (59-43-8)

Guidance literature:

With recombinant mouse thiamine pyrophosphokinase 1; magnesium sulfate; 5'-adenosine monophosphate; In aq. buffer; at 37 ℃; for 0.333333h; pH=7.5; Concentration; Equilibrium constant; Kinetics; Enzymatic reaction;

DOI:10.1016/j.bbagen.2021.130071

upstream raw materials:

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

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-2-hydroxymethyl-4-methyl-thiazolium; chloride monohydrochloride

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phenyl-methanone

Thiamine hydrochloride

Downstream raw materials:

1-[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-3-methoxy-3-phenyl-propan-1-one

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dimethyl ester

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibenzyl ester

[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phosphonic acid dibenzyl ester

Refernces

SYNTHESIS AND ANTIVITAMIN ACTIVITY OF HYDROXYTHIAMINE ESTERS WITH SUBSTITUTED PHTHALYL- AND DIHYDROFURYLACETIC ACIDS

10.1007/BF00772150

This research aims to synthesize and investigate new vitamin B1 antagonists that possess the advantages of hydroxythiamine (HT) but can penetrate nerve tissue, unlike HT. Hydroxythiamine (HT) is described as a widely used vitamin B1 antagonist. It is known for its ability to profoundly inhibit the activity of thiamine diphosphate-dependent enzymes in most tissues and organs of animals. However, HT is unable to penetrate the blood-brain barrier, which limits its antivitamin action on the brain. Vitamin B1, also known as thiamine, is essential for various metabolic processes in the body, and its diphosphate form is a cofactor for enzymes like transketolase (TK). The study aims to develop new vitamin B1 antagonists that retain the benefits of HT but can also affect nerve tissue, which HT cannot do due to its inability to cross the blood-brain barrier. The research concludes that these HT esters have a milder antivitamin action on most tissues and organs compared to HT but exhibit a stronger inhibitory effect on thiamine diphosphate-dependent enzymes in the brain. This suggests they could be effective as vitamin B1 antagonists with improved action in nerve tissue.