Showing chemical card for Thiamine mononitrate (CFc000012934)
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| Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2022-08-28 10:25:12 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2022-09-13 19:01:09 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemfont ID | CFc000012934 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecule Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | Thiamine mononitrate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Definition | Thiamine mononitrate is a nutrient supplement, used for the enrichment of flour mixes. Beriberi is a neurological and cardiovascular disease. The three major forms of the disorder are dry beriberi, wet beriberi, and infantile beriberi. Differential diagnosis include riboflavin deficiency and avian encephalomyelitis. In riboflavin deficiency, the "curled toes" is a characteristic symptom. Muscle tremor is typical of avian encephalomyelitis. Thiamine mononitrate is a therapeutic diagnosis can be tried by supplementing Vitamin B1 only in the affected bird. If the animals do not respond in a few hours, Vitamin B1 deficiency can be excluded. Genetic diseases of thiamine transport are rare but serious. Thiamine Responsive Megaloblastic Anemia with diabetes mellitus and sensorineural deafness (TRMA) is an autosomal recessive disorder caused by mutations in the gene SLC19A2, a high affinity thiamine transporter. TRMA patients do not show signs of systemic thiamine deficiency, suggesting redundancy in the thiamine transport system. This has led to the discovery of a second high affinity thiamine transporter, SLC19A3. Leigh Disease (Subacute Necrotising Encephalomyelopathy) is an inherited disorder which affects mostly infants in the first years of life and is invariably fatal. Pathological similarities between Leigh disease and WE led to the hypothesis that the cause was a defect in thiamine metabolism. Thiamine mononitrate is one of the most consistent findings has been an abnormality of the activation of the pyruvate dehydrogenase complex; Korsakoff Psychosis is generally considered to occur with deterioration of brain function in patients initially diagnosed with WE. This is an amnestic-confabulatory syndrome characterized by retrograde and anterograde amnesia, impairment of conceptual functions, and decreased spontaneity and initiative.<; The enzymes transketolase, pyruvate dehydrogenase (PDH) and 2-oxoglutarate dehydrogenase (OGDH) are all important in carbohydrate metabolism. The cytosolic enzyme transketolase is a key player in the pentose phosphate pathway required for the biosynthesis of NADPH and the pentose sugars deoxyribose and ribose. The mitochondrial PDH and OGDH are part of biochemical pathways that result in the generation of adenosine triphosphate (ATP), which is a major form of energy for the cell. PDH links glycolysis to the citric acid cycle, while the reaction catalyzed by OGDH is a rate-limting step in the citric acid cycle. In the nervous system, PDH is also involved in the production of acetylcholine, a neurotransmitter, and for myelin synthesis. The synthesis of thiamine diphosphate (ThDP), also known as thiamine pyrophosphate (TPP) or cocarboxylase, is catalyzed by an enzyme called thiamine diphosphokinase according to the reaction thiamine + ATP ThDP + AMP (EC 2.7.6.2). ThDP is a coenzyme for several enzymes that catalyze the transfer of two-carbon units and in particular the dehydrogenation (decarboxylation and subsequent conjugation with coenzyme A) of 2-oxoacids (alpha-keto acids). Examples include:; Thiamine hydrochloride is a food additive used to add a brothy/meaty flavor to gravies or soups. Thiamine is a colorless compound with a chemical formula C12H17N4OS. Its structure contains a pyrimidine ring and a thiazole ring linked by a methylene bridge. Thiamine is soluble in water, methanol, and glycerol and practically insoluble in acetone, ether, chloroform, and benzene. It is stable at acidic pH, but is unstable in alkaline solutions. Thiamine is unstable to heat, but stable during frozen storage. It is unstable when exposed to ultraviolet light and gamma irradiation. Thiamine reacts strongly in Maillard-type reactions. Thiamine, or thiamin, sometimes called aneurin, is a water-soluble vitamin of the B complex (vitamin B1), whose phosphate derivatives are involved in many cellular processes. The best characterized form is thiamine diphosphate (ThDP), a coenzyme in the catabolism of sugars and amino acids. In yeast, ThDP is also required in the first step of alcoholic fermentation. Wernicke s encephalopathy is the most frequently encountered manifestation of thiamine deficiency in Western society, though it may also occur in patients with impaired nutrition from other causes, such as gastrointestinal disease, those with HIV-AIDS, and with the injudicious administration of parenteral glucose or hyperalimentation without adequate B-vitamin supplementation. This is a striking neuro-psychiatric disorder characterized by paralysis of eye movements, abnormal stance and gait, and markedly deranged mental function. When Lohman and Schuster (1937) showed that the diphosphorylated thiamine derivative (thiamine diphosphate, ThDP) was a cofactor required for the oxydative decarboxylation of pyruvate, (a reaction now known to be catalyzed by pyruvate dehydrogenase), the mechanism of action of thiamine in the cellular metabolism seemed to be elucidated. Presently, this view seems to be oversimplified: pyruvate dehydrogenase is only one of several enzyme requiring thiamine diphosphate as cofactor, but moreover other thiamine phosphate derivatives have been discovered since then, and they may also contribute to the symptoms observed during thiamine deficiency. Thiamine mononitrate belongs to the family of Thiamines. These are compounds containing a thiamine moiety, which is structurally chracterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| Chemical Formula | C12H17N5O4S | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 327.359 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 327.100124747 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium nitrate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional Name | thiamine nitrate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 532-43-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | [O-]N(=O)=O.CC1=C(CCO)SC=[N+]1CC1=C(N)N=C(C)N=C1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C12H17N4OS.NO3/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;2-1(3)4/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);/q+1;-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | UIERGBJEBXXIGO-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Diazines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Pyrimidines and pyrimidine derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Thiamines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Functional Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physiological effect | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Disposition | Biological location
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| Process | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Role | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
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| HMDB ID | HMDB0031755 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | DBSALT001495 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FooDB ID | FDB008426 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Thiamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 10762 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Food Biomarker Ontology | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
