Grundinformationen
- Standard-SMILES
Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1.Cl.[Cl-]- InChIKey
DPJRMOMPQZCRJU-UHFFFAOYSA-M- Summenformel
- C12H17N4OS.ClH.Cl
- Durchschnittliche Molmasse
- 337,3 g/mol
- Monoisotopische Masse
- 336,05783756
Überblick
Thiamine hydrochloride is a hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid. It has a role as an insect repellent. It is a vitamin B1 and a hydrochloride. It contains a thiamine(2+).
Namen und Bezeichner
- Bevorzugter Name
- Thiamine Hydrochloride
- IUPAC
- 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride
- Lokaler Name
- Thiaminhydrochlorid
- Englischer Name
- Thiamine hydrochloride
- Summenformel
- C12H17N4OS.ClH.Cl
- Molmasse
- 337.27
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
67-03-8- PubChem CID
- 6202
- DTXSID
DTXSID0040622- ChEMBL
CHEMBL1200941- ChEBI
CHEBI:49105- UNII
- M572600E5P
- EC Number
- 200-641-8
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 104 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 268
Experimentelle und physikochemische Eigenschaften
Solubility
Soluble in water, propylene glycol; Insoluble in ether, benzene, hexane, chloroform
Slightly soluble (in ethanol)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical Description
Solid with a mild thiazole odor; [Merck Index] White to light yellow crystalline powder; Hygroscopic; [Alfa Aesar MSDS]
Small white to yellowish crystals or crystalline powder; slight characteristic odour reminescent of thiazole
Physikochemische Eigenschaften
- Schmelzpunkt
- 250 °C · 250 °C (dec.)(lit.)
- Dichte
- 1.3766 · 1.3766 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- FEMA
- 3322 · 3322 | THIAMINE HYDROCHLORIDE
- Flammpunkt
- 9 °C · 9°C
- storage temp.
- room temp
- Löslichkeit
- 2 O: · H2O: 0.1 g/mL at 20 °C, clear, colorless
- pka
- 4.8 · pKa 4.8 (Uncertain);9.0 (Uncertain)
- Aggregatzustand
- Crystalline Powder
- Farbe
- White to almost white
- PH
- 2.7 · 2.7-3.3
- Geruch (Odor)
- sour mild bitter
- Geruchsart
- bland
- Biologische Quelle
- synthetic (organic)
- Wasserlöslichkeit
- 1 g/mL · 1 g/mL
- Merck
- 14 · 14,9295
- JECFA Number
- 1030 · 1030
- BRN
- 3851771 · 3851771
- BCS Class
- 3 · 3
- Stabilität
- Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents.
- Major Application
- 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
- -3.93 · -3.93
- CAS Datenbank
- 67 · 67-03-8(CAS DataBase Reference)
- EPA chemische Informationen
- Thiamine hydrochloride (67-03-8)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 66.2% (247 of 373) of all reports.
Warning
H319 (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.
Gefahrenhinweise
Regulatory Information
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/26096
Thiamine hydrochloride: Non hazardous
Toxikologische Informationen
Toxicity Summary
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.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Thiamine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- F
- 3-8-10
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29362200
- RTECS-Nr.
- XI7350000
- risk_code
- 36/37/38-39/23/24/25-23/24/25-11
- Toxizität
- LD50 in mice (mg/kg): 89.2 i.v.; 8224 orally (Winter)
- hazard_code
- Xi,T,F
- safety_code
- 22-24/25-37/39-26-36-45-36/37-16-7
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
FDA Pharmacological Classification
METABOLIN
Increased Large Intestinal Motility [PE]; Cations, Divalent [CS]; Phosphate Chelating Activity [MoA]; Potassium Salt [EPC]; Stimulation Large Intestine Fluid/Electrolyte Secretion [PE]; Calcium [CS]; Potassium Compounds [CS]; Inhibition Small Intestine Fluid/Electrolyte Absorption [PE]; Amino Acids [CS]; Osmotic Laxative [EPC]; Magnesium Ion Exchange Activity [MoA]; Inhibition Large Intestine Fluid/Electrolyte Absorption [PE]; Increased Coagulation Factor Activity [PE]; Osmotic Activity [MoA]; Blood Coagulation Factor [EPC]; Phosphate Binder [EPC]; Calculi Dissolution Agent [EPC]; Amino Acid [EPC]
Verwendung und Herstellung
Uses
Used as a human and veterinary vitamin (enzyme cofactor); [Merck Index] An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and PELLAGRA. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. [ChemIDplus] Used as a flavoring agent and nutritional supplement for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. Thiamine (hydrochloride) is a food additive used to add a brothy/meaty flavor to gravies or soups.
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Skin conditioning
Anwendungen
BeschreibungThiamine 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.
OccurrenceRice 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.
HistoryThiamine 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.
VerwendenThiamine 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.
Darstellung
synthetischeBy linking the preformed thiazole and pyrimidine ring system.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: Thiamine hydrochloride is a hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid. It has a role as an insect repellent. It is a vitamin B1 and a hydrochloride. It contains a thiamine(2+).
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