CAS 136-09-4

Thiamine pyrophosphate

Description:

Thiamine pyrophosphate (TPP), also known as thiamine diphosphate, is the active form of vitamin B1 and plays a crucial role as a coenzyme in carbohydrate metabolism. It is characterized by its involvement in the decarboxylation of alpha-keto acids and the hexose monophosphate shunt, facilitating the conversion of carbohydrates into energy. TPP is a water-soluble compound, which means it readily dissolves in water, making it bioavailable for various biochemical processes. The substance is sensitive to heat and can be degraded by prolonged exposure to high temperatures or alkaline conditions. In terms of structure, TPP contains a thiazole ring and a pyrimidine ring, linked by a pyrophosphate group, which is essential for its enzymatic activity. Deficiency in thiamine can lead to metabolic disorders such as beriberi and Wernicke-Korsakoff syndrome. TPP is commonly found in foods such as whole grains, legumes, and pork, and is also available as a dietary supplement to support metabolic health.

Formula: C₁₂H₁₈N₄O₇P₂S

InChI: InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)

InChI key: InChIKey=AYEKOFBPNLCAJY-UHFFFAOYSA-N

SMILES: C([N+]=1C(C)=C(CCOP(OP(=O)(O)O)(=O)[O-])SC1)C=2C(N)=NC(C)=NC2

Synonyms:

• Lipothiamine pyrophosphate
• Thiamin pyrophosphate
• Thiamine pyrophosphate
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)-, hydroxide, inner salt, P,P'-dioxide
• 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)-, inner salt
• Thiazolium, 3-[(4-Amino-2-Methyl-5-Pyrimidinyl)Methyl]-5-[2-[[Hydroxy(Phosphonooxy)Phosphinyl]Oxy]Ethyl]-4-Methyl-, Inner Salt
• 2-(3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-4-methyl-1,3-thiazoniol-5-yl)ethyl dihydrogen diphosphate

Cocarboxylase

CAS: 136-09-4

Formula: C₁₂H₁₈N₄O₇P₂S

Color and Shape: White To Off-White Solid

Molecular weight: 424.30

Ref: 4Z-C-153001