Thiaminhydrochlorid
THIAMINE · THIAMINE HCL · thd · VITAMIN B1 HCL · VB1 HCL · THIAMIN HYDROCHLORIDE · Vitamin B1 Thiamine · VIT B1
Identifikatoren & physikalische Daten
| CAS No. | 67-03-8 |
|---|---|
| Summenformel | C12H17N4OS.ClH.Cl |
| Durchschnittliche Molmasse | 337,3 g/mol |
| Monoisotopische Masse | 336,05783756 g/mol |
| SMILES | Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1.Cl.[Cl-] |
| InChIKey | DPJRMOMPQZCRJU-UHFFFAOYSA-M |
| PubChem CID | 6202 |
| ChEMBL | CHEMBL1200941 |
| ChEBI | CHEBI:49105 |
| EC No. | 200-641-8 |
| DTXSID | DTXSID0040622 |
| Lokaler Name | Thiaminhydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 104 |
|---|---|
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 268 |
| Stoffklassen | Biological Agents -> Vitamins and Derivatives |
| Kosmetika | Skin conditioning |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | Soluble in water, propylene glycolInsoluble in ether, benzene, hexane, chloroformSlightly soluble (in ethanol)H2O: 0.1 g/mL at 20 °C, clear, colorless |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Physical Description | Solid with a mild thiazole odor[Merck Index] White to light yellow crystalline powderHygroscopic[Alfa Aesar MSDS]Small white to yellowish crystals or crystalline powderslight characteristic odour reminescent of thiazole |
| Schmelzpunkt | 250 °C (dec.)(lit.) |
| Dichte | 1.3766 (rough estimate) |
| Brechungsindex | 1.6000 (estimate) |
| FEMA | 3322 | THIAMINE HYDROCHLORIDE |
| Flammpunkt | 9°C |
| Lagerbedingungen | room temp |
| pKa (Säurekonstante) | pKa 4.8 (Uncertain)9.0 (Uncertain) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to almost white |
| pH | 2.7-3.3 |
| Geruch | sour mild bitter |
| Geruchsart | bland |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,9295 |
| JECFA Number | 1030 |
| BRN | 3851771 |
| BCS Class | 3 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONINGFRAGRANCE |
| InChI | 1S/C12H17N4OS.2ClH/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)2*1H/q+1/p-1 |
| InChIKey | DPJRMOMPQZCRJU-UHFFFAOYSA-M |
| SMILES | CC1=NC(N)=C(C[N+]2=CSC(CCO)=C2C)C=N1.Cl.[Cl-] |
| LogP (Verteilungskoeffizient) | -3.93 |
| CAS Datenbank | 67-03-8(CAS DataBase Reference) |
| EPA chemische Informationen | Thiamine hydrochloride (67-03-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 66.2% (247 of 373) of all reports.WarningH319 (33.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 373 reports by companies from 12 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride, hydrochloride (1:1:1)Regulation (EC) No 1831/2003 (amended)Status: Active Update: 16-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26096Thiamine hydrochloride: Non hazardous |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | Forms a hydrate on absorbing water from atmospheric humidity[Merck Index] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Alfa Aesar MSDS] See Thiamine. |
| Hazard Classes and Categories | Eye Irrit. 2 (33.2%) |
| Gesundheitliche Auswirkungen | There are no reports available of adverse effects from consumption of excess thiamine by ingestion of food and supplements. [Wikipedia] |
| Expositionspfade | Oralparenteral (intravenous, intramuscular). Absorbed mainly from duodenum, by both active and passive processes |
| Toxizitätsübersicht | It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. There are five known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and the recently discovered adenosine thiamine triphosphate (AThTP), and adenosine thiamine diphosphate. Each derivative has unique functions, however, most are involved as coenzymes. |
Anwendungen & Verwendung
Beschreibung
Thiamine Hydrochloride is the hydrochloride salt form of thiamine (vitamin B1), a vitamin essential for aerobic metabolism, cell growth, transmission of nerve impulses and acetylcholine synthesis. Vitamin B1 helps prevent various health problems including heart damage.Thiamine hydrochloride is used to prevent and treat thiamine deficiency states, which may occur as a result of inadequate nutrition or intestinal malabsorption. It is also used for the treatment of Wernicke-Korsakoff syndrome, beriberi and thiamine deficiency related to chronic alcoholism. Thiamine hydrochloride is used as a food additive to add brothy/meaty flavor to gravies or soups. It is used also as a food supplement and flavoring ingredient with a bitter taste.
Occurrence
Rice husks are reportedly the principal source of vitamin B1; in variable amounts it is a constituent of yeast, milk, green leaves, roots and tubers; it is also present in high concentration in seeds, and in lesser amount in different animal organs and muscles.
History
Thiamine hydrochloride was the first water-soluble vitamin to be purified. In 1912, Cashmir Funk isolated thiamine from rice husks and coined the term ‘vitamine’ because it was required for life (‘vita’) and because thiamine contained nitrogen (‘amine’). Thiamine, formerly known as B1, is water soluble. Thiamine is a vital cofactor for enzymes and coenzymes of glycolysis, the Kreb’s cycle, the pentose phosphate pathway. Thiamine is also involved in the biosynthesis of the neurotransmitters acetylcholine and gamma-aminobutyric acid and in nerve propagation.
Verwenden
Thiamine is the water-soluble vitamin b1, required for normal digestion and functioning of nerve tissues and in the prevention of beriberi. It also acts as a coenzyme in the metabolism of carbohydrates. During processing, the higher and longer the heating period, the greater the loss. The loss is reduced in the presence of acid. Thiamine hydrochloride and thiamine mononitrate are two available forms. The mononitrate form is less hygroscopic and more stable than the hydrochloride form, making it suitable for use in beverage powders. It is used in enriched flour and is found as thiamine mononitrite in frozen egg substitute and crackers.
Herstellung & Synthese
synthetische
By linking the preformed thiazole and pyrimidine ring system.