Thiaminhydrochlorid

Thiamine Hydrochloride

HCID 6202CAS 67-03-8

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

THIAMINE HYDROCHLORIDE67-03-8Thiamine HCLAneurine hydrochlorideVitamin B1 hydrochlorideClotiaminaEskaphenBetalin SThiamine chloride hydrochlorideThiamine dichlorideBevitineBenerva
Weitere Namen anzeigen
THIAMINEthdVITAMIN B1 HCLVB1 HCLVitamin B1 ThiamineVIT B1FEMA 3322200-641-8
Thiamin chlorideThiaminum hydrochloricumThiamin hydrochlorideBiamineBetabion hydrochlorideFEMA No. 3322Thiamin dichlorideThiaminium chloride hydrochloride

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Vitamins and Derivatives
CosmeticsSkin conditioning
Food AdditivesFLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 Einträge

Soluble in water, propylene glycol; Insoluble in ether, benzene, hexane, chloroform

Slightly soluble (in ethanol)

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 4 Einträge

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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryForms 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 CategoriesEye Irrit. 2 (33.2%)

Toxikologische Informationen

Health EffectsThere are no reports available of adverse effects from consumption of excess thiamine by ingestion of food and supplements. [Wikipedia]
Exposure RoutesOral; parenteral (intravenous, intramuscular). Absorbed mainly from duodenum, by both active and passive processes
Toxicity Summary · 1 Eintrag

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Thiamine hydrochloride

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Toxicity DataLD50: 8224 mg/kg (Oral, Mouse) (A308) LD50: 3710 mg/kg (Oral, Rat) (A308)

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

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic
FDA Pharmacological Classification · 2 Einträge

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 · 2 Einträge

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.

Household ProductsInformation on 5 consumer products that contain Thiamine hydrochloride in the following categories is provided:
Use Classification · 5 Einträge

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

General Manufacturing InformationThiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride, hydrochloride (1:1:1): ACTIVE
Anwendungen · 4 Einträge

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.

Anbieter50 Anbieter

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Ergänzende Hinweise · 1 Eintrag

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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