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Encyclopedia > Thiamine
Thiamine
IUPAC name 2-[3-[(4-amino-2-methyl- pyrimidin-5-yl)methyl]- 4-methyl-thiazol-5-yl] ethanol
Identifiers
CAS number 59-43-8
PubChem 1130
MeSH Thiamine
SMILES [Cl-].Cc1c(CCO)sc[n+]1Cc2cncnc2N
Properties
Molecular formula C12H17N4OS+
Molar mass 265.356
Melting point

248-260 °C (hydrochloride salt) Image File history File links Download high-resolution version (1100x423, 31 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Thiamine ... Image File history File links Download high-resolution version (1100x573, 159 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Thiamine User:Benjah-bmm27/Gallery User:Ben Mills/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article or section does not cite any references or sources. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references
For the similarly spelled nucleic acid, see Thymine

Thiamine or thiamin, also known as vitamin B1, is one of the B vitamins. It is a colorless compound with chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Its chemical structure contains a pyrimidine ring and a thiazole ring. In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... For the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Retinol (Vitamin A) For the record label, see Vitamin Records A vitamin is an organic compound required in tiny amounts for essential metabolic reactions in a living organism. ... The B vitamins are eight water-soluble vitamins that play important roles in cell metabolism. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... It has been suggested that this article or section be merged with Solution. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Functional group of an alcohol molecule. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ... Thiazole, or 1,3-thiazole, is a clear to pale yellow flammable liquid and pyridine-like odor with the molecular formula C3H3NS. It is a 5-membered ring, in which two of the vertices of the ring are nitrogen and sulfur, and the other three are carbons [1]. Thiazole is...

Contents

History

Thiamine was first discovered in 1910 by Umetaro Suzuki in Japan when researching how rice bran cured patients of beriberi. He named it aberic acid. He did not determine its chemical composition, nor that it was an amine. Suzuki Umetaro (鈴木梅太郎, April 7, 1874 – September 20, 1943) was a Japanese scientist. ... This article needs additional references or sources for verification. ... // wheat bran Bran is the hard outer layer of and consists of combined aleurone and pericarp. ... Beriberi is a nervous system ailment caused by thiamine (vitamin B1) deficiency. ...


It was first crystallized by Jansen and Donath in 1926 (they named it aneurin, for antineuritic vitamin).


Its chemical composition and synthesis was finally reported by Robert R. Williams in 1935. He also coined the name for it, thiamine. Robert R. Williams (February 16, 1886–October 2, 1965) was an American telephone company researcher who carried out vitamin research in his spare time and established the structure of thiamine (vitamin B1). ...


Thiamine phosphate derivatives

There are four known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), thiamine triphosphate (ThTP) and the recently discovered adenosine thiamine triphosphate (AThTP). Thiamine monophosphate is a thiamine derivative. ... Cocarboxylase is the diphosphoric ester of thiamin (thiamine). ... Thiamine triphosphate (ThTP) is found in most organisms, bacteria, fungi, plants and animals 1. ... Adenosine thiamine triphosphate (AThTP), or thiaminylated ATP, was discovered in Escherichia coli where it may account for up to 15 - 20 % of total thiamine under carbon starvation. ...


Thiamine pyrophosphate

Thiamine pyrophosphate (TPP), also known as thiamine diphosphate (ThDP), is a coenzyme for several enzymes that catalyze the dehydrogenation (decarboxylation and subsequent conjugation to Coenzyme A) of alpha-keto acids. Examples include: Thiamine mononitrate Thiamine or thiamin, also known as vitamin B1, is a colorless compound with chemical formula C12H17ClN4OS. It is soluble in water and insoluble in alcohol. ... Coenzyme A Coenzymes are small organic non-protein molecules that carry chemical groups between enzymes. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ...

TPP is synthesized by the enzyme thiamine pyrophosphokinase, which requires free thiamine, magnesium, and adenosine triphosphate. Orders Subclass Monotremata Monotremata Subclass Marsupialia Didelphimorphia Paucituberculata Microbiotheria Dasyuromorphia Peramelemorphia Notoryctemorphia Diprotodontia Subclass Placentalia Xenarthra Dermoptera Desmostylia Scandentia Primates Rodentia Lagomorpha Insectivora Chiroptera Pholidota Carnivora Perissodactyla Artiodactyla Cetacea Afrosoricida Macroscelidea Tubulidentata Hyracoidea Proboscidea Sirenia The mammals are the class of vertebrate animals primarily characterized by the presence of mammary... Pyruvate dehydrogenase is an enzyme (E1) in the pyruvate dehydrogenase complex (PDC). ... Oxoglutarate dehydrogenase (aka α-ketoglutarate dehydrogenase) is an enzyme (EC 1. ... A few of the metabolic pathways in a cell. ... Lactose is a disaccharide found in milk. ... The branched-chain alpha-keto acid dehydrogenase complex is a combination of enzymes responsible for the degradation of the branched chain amino acids (valine, leucine, and isoleucine). ... 2-Hydroxyphytanoyl-CoA lyase is a peroxisomal enzyme involved in the catabolism of phytanoic acid. ... Transketolase, an enzyme that transfer a 2 Carbon unit(the critical part that determine it is a ketone)from a ketose to an aldose. ... The pentose phosphate pathways Nonoxidative phase The pentose phosphate pathway (also called Phosphogluconate Pathway, or Hexose Monophosphate Shunt [HMP shunt]) is a process that serves to generate NADPH and the synthesis of pentose (5-carbon) sugars. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ... Magnification of grains of sugar, showing their monoclinic hemihedral crystalline structure. ... Deoxyribose Deoxyribose, also known as D-Deoxyribose and 2-deoxyribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Ribose Ribose, primarily seen as D-ribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Pyruvate decarboxylase is a homotetrameric enzyme(EC 4. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic microorganisms classified in the kingdom Fungi. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Thiamine pyrophosphokinase is a phosphotransferase enzyme that catalyzes the transfer of a pyrophosphate moiety from adenosine triphosphate to thiamine, to give thiamine pyrophosphate, the coenzyme form of thiamine. ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white solid at room temp Standard atomic weight 24. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ...


Thiamine triphosphate

Thiamine triphosphate (ThTP) was long considered a specific neuroactive form of thiamine. Thiamine triphosphate (ThTP) is found in most organisms, bacteria, fungi, plants and animals 1. ...


However, recently it was shown that ThTP exists in bacteria, fungi, plants and animals suggesting a much more general cellular role. In particular in E. coli it seems to play a role in response to amino acid starvation. Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ... u fuck in ua ... The word Animals when used alone has several possible meanings in the English language. ... Binomial name Escherichia coli T. Escherich, 1885 Escherichia coli (usually abbreviated to E. coli) is one of the main species of bacteria that live in the lower intestines of warm-blooded animals (including birds and mammals) and are necessary for the proper digestion of food. ...


Adenosine thiamine triphosphate

Adenosine thiamine triphosphate (AThTP) or thiaminylated adenosine triphosphate has recently been discovered in Escherichia coli where it accumulates as a result of carbon starvation. In E. coli, AThTP may account for up to 20 % of total thiamine. Adenosine thiamine triphosphate (AThTP), or thiaminylated ATP, was discovered in Escherichia coli where it may account for up to 15 - 20 % of total thiamine under carbon starvation. ... E. coli redirects here. ...


It also exists in lesser amounts in yeast, roots of higher plants and animal tissues. Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic microorganisms classified in the kingdom Fungi. ...


Nutrition

Also known as vitamin B1, thiamine plays an important role in helping the body metabolize carbohydrates and fat to produce energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine is water-soluble and cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.


Good sources

Thiamine is found naturally in the following foods, each of which contains at least 0.1 mg of the vitamin per 28-100 g (1-3.5 oz): Green peas, Spinach, Liver, Beef, Pork, Navy beans, Nuts, Pinto beans, Bananas, Soybeans, Whole-grain and Enriched Cereals, Breads, Yeast,the aleurone layer of unpolished rice, and Legumes. А Binomial name Pisum sativum L. A pea is the small, edible round green bean which grows in a pod on the leguminous vine Pisum sativum. ... Binomial name Spinacia oleracea L. Percentages are relative to US recommendations for adults. ... The liver is an organ present in vertebrates and some other animals. ... For other uses, see Beef (disambiguation). ... Two halves of pork being delivered Pork is the culinary name for meat from pigs. ... Binomial name Phaseolus vulgaris L. Navy Bean redirects here. ... Hazelnuts from the Common Hazel Chestnut A nut can be either a seed or a fruit. ... Binomial name Phaseolus vulgaris L. Navy Bean redirects here. ... This article or section does not cite its references or sources. ... Binomial name Glycine max Soybeans (US) or soya beans (UK) (Glycine max) are a high-protein legume (Family Fabaceae) grown as food for both humans and livestock. ... This article or section does not cite its references or sources. ... This article is about cereals in general. ... Percentages are relative to US recommendations for adults. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic microorganisms classified in the kingdom Fungi. ... Aleurone (from Greek aleuron, flour) is a protein found in the endosperm of many seeds. ... This article needs additional references or sources for verification. ... Varieties of soybean seeds, a popular legume Pea pods A legume is a plant in the family Fabaceae (or Leguminosae), or a fruit of these plants. ...


Deficiency

Systemic thiamine deficiency can lead to myriad problems including neurodegeneration, wasting, and death. A lack of thiamine can be caused by malnutrition, alcoholism, a diet high in thiaminase-rich foods (raw freshwater fish, raw shellfish, ferns) and/or foods high in anti-thiamine factors (tea, coffee, betel nuts)[1]. Neurodegeneration is progressive loss of structure or function of neurons, including death of neurons. ... Percentage of population affected by malnutrition by country, according to United Nations statistics. ... Alcoholism is the consumption of, or preoccupation with, alcoholic beverages to the extent that this behavior interferes with the drinkers normal personal, family, social, or work life, and may lead to physical or mental harm. ... Thiaminase is an enzyme (EC 2. ... Cooked mussels Shellfish is a term used to describe shelled molluscs and crustaceans used as food. ... Classes Psilotopsida Equisetopsida Marattiopsida Pteridopsida (Polypodiopsida) this dnt make sense A fern is any one of a group of about 20,000 species of plants classified in the phylum or division Pteridophyta, also known as Filicophyta. ... Tea leaves in a Chinese gaiwan. ... A cup of coffee Workers sorting and pulping coffee beans in Guatemala Mature coffee fruit still on the plant Coffee is a widely consumed beverage prepared from the roasted seeds — commonly referred to as beans — of the coffee plant. ... Binomial name Areca catechu Linnaeus Areca nut, or pinang, more commonly known as betel nut, is the seed of the betel palm or Areca catechu, a species of palm tree which grows throughout the Pacific, Asia, and parts of east Africa. ...


Well-known syndromes caused by thiamine deficiency include Wernicke-Korsakoff syndrome and beriberi, diseases also common with chronic alcoholism. Wernicke-Korsakoff syndrome is a combination of Korsakoffs syndrome, which is characterized by confusion, severe anterograde and retrograde amnesia and confabulation; and Wernickes encephalopathy, which is characterized by nystagmus, ophthalmoplegia, coma and, if untreated, death. ... Beriberi is a nervous system ailment caused by thiamine (vitamin B1) deficiency. ...


Diagnostic testing for B1 deficiency

A positive diagnosis test for Thiamine deficiency can be ascertained by measuring the activity of transketolase in erythrocyte . Thiamine can also be skeeted directly in whole blood following the conversion of thiamine to a fluorescent thiochrome derivative. Transketolase, an enzyme that transfer a 2 Carbon unit(the critical part that determine it is a ketone)from a ketose to an aldose. ... Human red blood cells Red blood cells are the most common type of blood cell and are the vertebrate bodys principal means of delivering oxygen to body tissues via the blood. ... Fluorescence induced by exposure to ultraviolet light in vials containing various sized cadmium selenide (CdSe) quantum dots. ...


Genetic diseases

Genetic diseases of thiamine transport are rare but serious. Thiamine Responsive Megaloblastic Anemia with diabetes mellitus and sensorineural deafness (TRMA)[2] is an autosomal recessive disorder caused by mutations in the gene SLC19A2,[3] 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.[4] Image File history File links Splitsection. ... SLC19A2 is a thiamine transporter. ... SLC19A3 is a thiamine transporter. ...


Mendelian Inheritance in Man (OMIM) 249270 The Mendelian Inheritance in Man project is a database that catalogues all the known diseases with a genetic component, and - when possible - links them to the relevant genes in the human genome. ...


Research

High doses

The RDA in most countries is set at about 1.4 mg. However, tests on volunteers at daily doses of about 50 mg have shown an increase in mental acuity. [5] Reference Daily Intake (RDI) is the daily dietary intake level of a nutrient considered sufficient to meet the requirements of nearly all (97–98%) healthy individuals in each life-stage and gender group. ...


Thiamine as an insect repellent

Some studies suggest that taking thiamine (vitamin B1) 25 mg to 50 mg three times per day is effective in reducing mosquito bites. A large intake of Thiamine produces a skin odor that is not detectable by humans, but is disagreeable to female mosquitoes.[6] Thiamine takes more than 2 weeks before the odor fully saturates the skin. With the advances in topical preparations there is an increasing number of Thiamine based repellent products. Whilst there is considerable anecdotal evidence of Thiamine products being effective in the field (Australia, US and Canada), there has yet to be any clinical trials run to demonstrate the efficacy of these products.


Benefits for autism

Derrick Lonsdale led a successful study on the treatment of autism spectrum children with a derivative of thiamine known as thiamine tetrahydrofurfuryl disulfide.[7] This work is controversial linking diet with autism. Derrick Lonsdale Derrick Lonsdale (born 1924) M.D., Fellow of the American College of Nutrition (FACN), Fellow of the American College for Advancement in Medicine (FACAM)[1] is a pediatrican and researcher into the benefits of certain nutrients in preventing disease and and psychotic behavior. ... Autism is a brain development disorder that shows symptoms before a child is three years old and has a steady course with no remission. ...


References

  1. ^ "Thiamin", Jane Higdon, Micronutrient Information Center, Linus Pauling Institute
  2. ^ Thiamine Responsive Megaloblastic Anemia with severe diabetes mellitus and sensorineural deafness (TRMA) PMID 249270
  3. ^ SLC19A2 PMID 603941
  4. ^ SLC19A3 PMID 606152
  5. ^ Thiamine's Mood-Mending Qualities, Richard N. Podel, Nutrition Science News, January 1999.
  6. ^ Pediatric Clinics of North America, 16:191, 1969
  7. ^ Lonsdale D, Shamberger RJ, Audhya T (2002). "Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study". Neuro Endocrinol. Lett. 23 (4): 303-8. PMID 12195231. 

External links


  Results from FactBites:
 
Thiamine - Wikipedia, the free encyclopedia (602 words)
Thiamine was first discovered in 1910 by Umetaro Suzuki of Japan when researching how rice bran cured patients of Beriberi.
Thiamine pyrophosphate (TPP) is a coenzyme for pyruvate dehydrogenase, α-ketoglutarate dehydrogenase, branched-chain alpha-keto acid dehydrogenase, and transketolase.
TPP is synthesized by the enzyme thiamine pyrophosphokinase, which requires free thiamine, magnesium, and adenosine triphosphate.
  More results at FactBites »

 

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