Thiothiamine

Base Information

• Chemical Name: Thiothiamine
• CAS No.: 299-35-4
• Molecular Formula: C12H16N4OS2
• Molecular Weight: 296.417
• European Community (EC) Number: 206-077-9
• UNII: J8QL0N8LM4
• DSSTox Substance ID: DTXSID60184012
• Nikkaji Number: J5.468B
• Wikidata: Q72508934
• Mol file: 299-35-4.mol

Synonyms:Thiothiamine;299-35-4;Thioxothiamine;3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazole-2-thione;J8QL0N8LM4;3-(4-Amino-2-methylpyrimidin-5-ylmethyl)-5-(2-hydroxyethyl)-4-methylthiazole-2(3H)-thione;Thiothiamine 100 microg/mL in Acetonitrile;3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazole-2(3H)-thione;Thiothiamin;2(3H)-Thiazolethione,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-;3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methylthiazol-2(3H)-thione (Thioxothiamine);Thiamine Impurity E;Solbone;Thiamine EP Impurity E;UNII-J8QL0N8LM4;SCHEMBL7762802;DTXSID60184012;EINECS 206-077-9;THIOXOTHIAMINE [EP IMPURITY];CS-O-31156;3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-2(3H)-thiazolethione;CS-0166205;CS-0368602;FT-0675197;D87843;EC 206-077-9;EN300-1699784;THIAMINE NITRATE IMPURITY E [EP IMPURITY];THIAMINE HYDROCHLORIDE IMPURITY E [EP IMPURITY];Z3014786983;2(3H)-THIAZOLETHIONE, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-;3-((4-AMINO-2-METHYLPYRIMIDIN-5-YL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-1,3-THIAZOL-2(3H)-THIONE;3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazole-2(3H)-thione? (Vitamin Impurity;3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-2,3-dihydro-1,3-thiazole-2-thione;4-THIAZOLINE-2-THIONE, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-

Chemical Property of Thiothiamine

Chemical Property:

• Vapor Pressure: 3.28E-11mmHg at 25°C
• Melting Point: 238-239 °C
• Refractive Index: 1.709
• Boiling Point: 509.6 °C at 760 mmHg
• PKA: 14.72±0.10(Predicted)
• Flash Point: 262 °C
• PSA: 137.29000
• Density: 1.42g/cm³
• LogP: 2.43240
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 296.07655349
• Heavy Atom Count: 19
• Complexity: 388

Purity/Quality:

99.9% ^*data from raw suppliers

Thiothiamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC(=S)N1CC2=CN=C(N=C2N)C)CCO
• Uses: Thiothiamine is an impurity of Thiamine (T344185). Thiothiamine inhibits the activity of glutamate decarboxylase and decreases the concentration of GABA in brain tissue. Thiamine Impurity A

Technology Process of Thiothiamine

There total 20 articles about Thiothiamine 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:

Thiamine hydrochloride (67-03-8,70732-86-4) → thiamine thiazolone (490-82-4) + 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione (299-35-4)

Guidance literature:

With KO₂; In dimethyl sulfoxide; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)98871-3

Reference yield:

2-methyl-propan-1-ol (78-83-1) + thiamine disulfide (100502-51-0) → thiamine thiazolone (490-82-4) + 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione (299-35-4)

Guidance literature:

at 120 ℃;

DOI:10.1039/j39680002871 DOI:10.1039/jr9510000534

Reference yield:

2-methyl-propan-1-ol (78-83-1) + N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-1-methyl-2-methyldisulfanyl-but-1-en-t-yl)-formamide (2281-20-1) → thiamine thiazolone (490-82-4) + 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione (299-35-4)

Guidance literature:

at 120 ℃;

upstream raw materials:

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-tetrahydro-furo[2,3-d]thiazole-2-thione

Aneurin

1-thiopropane

thiamine disulfide

Downstream raw materials:

vitamin B₁ mononitrate

vitamin B₁

thiamine thiazolone

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-methyl-5-[2-(3-nitro-benzoyloxy)-ethyl]-3H-thiazole-2-thione

Refernces

• 1、 Dondoni, Alessandro,Galliani, Guido,Mastellari, Annarosa,Medici, Alessandro. "REACTION OF N-ALKYLTHIAZOLIUM HALIDES, INCLUDING THIAMINE, WITH SUPEROXIDE ION. CHEMISTRY AND BIOLOGICAL IMPLICATIONS.". . p. 2917 - 2920. Retrieved 2007/10/02.