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thiamine pyrophosphate chloride
vitamin B1 pyrophosphate chloride

Supplier Sponsors

Name:2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate chloride
CAS Number: 154-87-0Picture of molecule3D/inchi
Other(deleted CASRN):55056-45-6
ECHA EINECS - REACH Pre-Reg:205-836-1
FDA UNII: XMK8K8EVIU
Beilstein Number:3875902
MDL:MFCD00038740
Molecular Weight:460.77035400
Formula:C12 H19 Cl N4 O7 P2 S
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:nutrient supplements, EFSA concludes: use is of safety concern.
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 93.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in:
 water, 2613 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
Thiamine pyrophosphate hydrochloride
Odor: characteristic
Use: Thiamine pyrophosphate hydrochloride is a thiamine derivative produced by the enzyme thiamine diphosphokinase.
EMD Millipore
For experimental / research use only.
Cocarboxylase chloride
sds
Glentham Life Sciences
Thiamine pyrophosphate
Indis NV
For experimental / research use only.
Thiamine Pyrophosphate Chloride
Santa Cruz Biotechnology
For experimental / research use only.
Thiamine pyrophosphate ≥96%
Sigma-Aldrich: Sigma
For experimental / research use only.
Thiamine pyrophosphate ≥95%
sds
TCI AMERICA
For experimental / research use only.
Thiamine Pyrophosphate Chloride >98.0%(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 5000 mg/kg
Drugs in Japan Vol. -, Pg. 471, 1995.

intravenous-rat LD50 465 mg/kg
Drugs in Japan Vol. -, Pg. 471, 1995.

intravenous-mouse LD50 360 mg/kg
Drugs in Japan Vol. -, Pg. 471, 1995.

intramuscular-mouse LD50 > 1000 mg/kg
PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE BEHAVIORAL: ANTIPSYCHOTIC BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 1025, 1985.

intramuscular-rat LD50 > 500 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE BEHAVIORAL: ANTIPSYCHOTIC
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 1025, 1985.

Dermal Toxicity:
subcutaneous-mouse LD50 2500 mg/kg
Drugs in Japan Vol. -, Pg. 471, 1995.

subcutaneous-rat LD50 5000 mg/kg
Drugs in Japan Vol. -, Pg. 471, 1995.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
nutrient supplements, EFSA concludes: use is of safety concern.
Recommendation for thiamine pyrophosphate chloride usage levels up to:
 not for fragrance use.
 
Recommendation for thiamine pyrophosphate chloride flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Benfotiamine, thiamine monophosphate chloride and thiamine pyrophosphate chloride, as sources of vitamin B1 added for nutritional purposes to food supplements - Scientific Opinion of the Panel on Food Additives and Nutrient Sources added to Food (ANS)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):154-87-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9068
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate chloride
Chemidplus:0000154870
RTECS:XI7552000 for cas# 154-87-0
 
References:
 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate chloride
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9068
Pubchem (sid):134974097
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):D01225
HMDB (The Human Metabolome Database):HMDB01372
FooDB:FDB022584
YMDB (Yeast Metabolome Database):YMDB00381
Export Tariff Code:2936.22.0000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium chloride p,p'-dioxide
3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium chloride
3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-[2-[[hydroxy(phosphonooxy)phosphinyl]oxy]ethyl]-4-methylthiazolium chloride
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate chloride
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium chloride
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-diphosphoethyl)-4-methyl-1,3-thiazolium chloride
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(diphosphooxy)ethyl]-4-methyl-1,3-thiazol-3-ium chloride
 bioxilasi
 bioxylasi
 cocarboxil
 cocarboxylase
 cocarboxylasum
 coenzymate
 diphosphothiamine
 metabolase
 pyrophosphoric ester of thiamine
 thiamin diphosphate chloride
 thiamine diphosphate
 thiamine diphosphate chloride
 thiamine diphosphate ester chloride
 thiamine pyrophosphoric acid ester chloride
 thiamine pyrophosphoric ester
 thiamine(1+) diphosphate chloride
 thiaminium pyrophosphate chloride
 thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride, P,P'-dioxide
 thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride, P,P'-dioxide, tetrahydrate
 thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride
 thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-[2-[[hydroxy(phosphonooxy)phosphinyl]oxy]ethyl]-4-methyl-, chloride (1:1)
 vitamin B1 pyrophosphate chloride
 

Articles:

PubMed:A novel ultrasensitive phosphate amperometric nanobiosensor based on the integration of pyruvate oxidase with highly ordered gold nanowires array.
PubMed:Dispersive liquid-liquid microextraction coupled to liquid chromatography for thiamine determination in foods.
PubMed:The upregulation of thiamine (vitamin B1) biosynthesis in Arabidopsis thaliana seedlings under salt and osmotic stress conditions is mediated by abscisic acid at the early stages of this stress response.
PubMed:The advanced glycation end product-lowering agent ALT-711 is a low-affinity inhibitor of thiamine diphosphokinase.
PubMed:Effect of thiamine pyrophosphate on levels of serum lactate, maximum oxygen consumption and heart rate in athletes performing aerobic activity.
PubMed:Changes in ECG and enzyme activity in rat heart after myocardial infarction: effect of TPP and MnCl2.
PubMed:Modulation of thiamine metabolism in Zea mays seedlings under conditions of abiotic stress.
PubMed:Potent radical-scavenging activities of thiamin and thiamin diphosphate.
PubMed:Which stage of the process of apotransketolase interaction with thiamine diphosphate is affected by the regulatory activity of the donor substrate?
PubMed:Thermococcus profundus 2-ketoisovalerate ferredoxin oxidoreductase, a key enzyme in the archaeal energy-producing amino acid metabolic pathway.
PubMed:Donor substrate regulation of transketolase.
PubMed:[The effect of cocarboxylase treatment on erythrocyte transketolase and blood thiamine in patients with end stage renal disease undergoing maintenance hemodialysis].
PubMed:A non-cofactor role of thiamine derivatives in excitable cells?
PubMed:Thiamine in excitable tissues: reflections on a non-cofactor role.
PubMed:Chloride permeability of rat brain membrane vesicles correlates with thiamine triphosphate content.
PubMed:[Paracatalytic inactivation of pyruvate decarboxylase in the presence of quinones].
PubMed:Metabolism of thiamine triphosphate in rat brain: correlation with chloride permeability.
PubMed:Purification and characterization of indolepyruvate decarboxylase. A novel enzyme for indole-3-acetic acid biosynthesis in Enterobacter cloacae.
PubMed:Pyrophosphate-induced acidification of trans cisternal elements of rat liver Golgi apparatus.
PubMed:Measurement of alpha-ketoglutarate dehydrogenase activity in tissue extracts and human platelets using reversed-phase high-performance liquid chromatography.
PubMed:Bovine heart pyruvate dehydrogenase kinase stimulation by alpha-ketoisovalerate.
PubMed:Regulation of ion uptake in membrane vesicles from rat brain by thiamine compounds.
PubMed:Ultrastructural localization of phosphatase activity in the guinea pig pineal gland by the cerium technique.
PubMed:[Modification of the pharmacokinetics of ortophen and its analgesic activity by inducers and inhibitors of xenobiotic metabolism enzymes and thiamine diphosphate].
PubMed:Preparation and in vitro cytotoxicity of a methotrexate-anti-MM46 monoclonal antibody conjugate via an oligopeptide spacer.
PubMed:Cytotoxicities of two disulfide-bond-linked conjugates of methotrexate with monoclonal anti-MM46 antibody.
PubMed:Elucidation of the 2-aminoethylphosphonate biosynthetic pathway in Tetrahymena pyriformis.
PubMed:Rat brain apotransketolase: activation and inactivation.
PubMed:[Influence of enzyme inducers and inhibitors of the metabolism of xenobiotics and of the coenzyme forms of vitamins B1 and B2 on the anti-inflammatory effect of voltaren].
PubMed:Isolation of transketolase from rabbit liver and comparison of some of its kinetic properties with transketolase from other sources.
PubMed:Thiamin uptake in Euglena gracilis.
PubMed:[Advantages of oxythiamine bromide as a specific inhibitor of activity of thiamine-dependent enzymes].
PubMed:Effects of alpha-ketoisovalerate on bovine heart pyruvate dehydrogenase complex and pyruvate dehydrogenase kinase.
PubMed:Pyruvate dehydrogenase complex from ribbed mussel gill mitochondria.
PubMed:Pyruvate Decarboxylase from Zea mays L. : 2. Examination of Hysteretic Kinetics.
PubMed:[Correction of microcirculatory disorders in the surgical treatment of late-stage mitral stenosis].
PubMed:Inhibition of cell proliferation and dihydrofolate reductase by liposomes containing methotrexate-dimyristoylphosphatidylethanolamine derivatives and by the glycerophosphorylethanolamine analogs.
PubMed:Radiometric assay for thiamine pyrophosphokinase activity in human leukocytes.
PubMed:Purification of a branched-chain keto acid dehydrogenase from Pseudomonas putida.
PubMed:[Pig liver transketolase: covalent binding between the coenzyme and protein].
PubMed:The effect of intoxication by ceresan on the activity of phosphatases and esterases in the rat thalamus.
PubMed:[Effect of oxygen, water and hydrophobic medium in model reactions of thiamine pyrophosphate].
PubMed:An investigation into the effect on cigarette smoking of a new anti-smoking chewing gum.
PubMed:Acute life endangering ethanol intoxication treated in the intensive medical care unit.
PubMed:[Accidental poisoning with zinc chloride].
PubMed:[Evaluation of some methods of treating cardiac arrhythmias].
PubMed:[Treatment of acute hepatic insufficiency (a survey of the literature)].
PubMed:[Pathogenetic therapy of patients with pulmonary suppurations].
PubMed:[Acid-base equilibrium and its correction in parturients with arterial hypotension].
PubMed:Biogenesis of cocarboxylase in Escherichia coli: a novel enzyme catalyzing the formation of thiamine pyrophosphate from thiamine monophosphate.
PubMed:Effects of monovalent cations and ATP on brain thiamine diphosphatase of normal rats.
PubMed:Evidence for tighter binding of magnesium-thiamine pyrophosphate to -ketoglutarate dehydrogenase when activated by adenosine monophosphate.
PubMed:Studies on the influence of thiamine on the synthesis of thiamine pyrophosphate-dependent enzymes in Saccharomyces cerevisiae.
PubMed:Mechanisms of thiamine-catalyzed reactions. Decarboxylation of 2-(1-carboxy-1-hydroxyethyl)-3,4-dimethylthiazolium chloride.
PubMed:Coenzyme interactions. IV. Molecular complexes of thiamine with indole derivatives--quantitative aspects.
PubMed:[On the demonstration of thiaminpyrophosphatase ("Golgiphosphatase") in blood and bone marrow cells].
PubMed:[Degradation of uric acid and biosynthesis of the enzymes uricase, glyoxylate carboligase and urease in Hydrogenomonas H 16. I. Formation of glyoxylate carboliase and D-glycerate-3 dehydrogenase].
PubMed:[Studies on the effects of various drugs on the changes of aspartate aminotransferase (2.6.1.1)-isozyme in experimental myocardial infarction].
PubMed:[THERAPY OF AURICULAR FIBRILLATION].
 
Notes:
the coenzyme form of vitamin b1 present in many animal tissues. it is a required intermediate in the pyruvate dehydrogenase complex and the ketoglutarate dehydrogenase complex. Thiamine pyrophosphate is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents, including neurotransmitters, and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis; the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. The thiamine pyrophosphate dependence of the third step is unique in peroxisomal mammalian enzymology. Human pathology due to a deficient alpha-oxidation is mostly linked to mutations in the gene coding for the second enzyme of the sequence, phytanoyl-CoA hydroxylase (EC 1.14.11.18). (PMID: 12694175, 11899071, 9924800) [HMDB]
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