CAS 10055-47-7

2-(α-Hydroxyethyl)thiamine diphosphate

Description:

2-(α-Hydroxyethyl)thiamine diphosphate, commonly known as thiamine diphosphate (TDP) or thiamine pyrophosphate (TPP), is a biologically active form of vitamin B1. It plays a crucial role as a coenzyme in carbohydrate metabolism, particularly in the decarboxylation of alpha-keto acids and the pentose phosphate pathway. This compound is characterized by its diphosphate group, which is essential for its enzymatic activity, allowing it to participate in various biochemical reactions. TDP is soluble in water, which facilitates its transport and function within biological systems. Its structure includes a thiazole ring and a pyrimidine ring, contributing to its stability and reactivity. As a cofactor, it is vital for the functioning of several enzymes, including pyruvate dehydrogenase and transketolase. Deficiency in thiamine or its active form can lead to metabolic disorders, highlighting its importance in human health. Overall, 2-(α-Hydroxyethyl)thiamine diphosphate is integral to energy metabolism and cellular function.

Formula: C₁₄H₂₃N₄O₈P₂S

InChI: InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6,9,19H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p+1

InChI key: InChIKey=RRUVJGASJONMDY-UHFFFAOYSA-O

SMILES: C([N+]1=C(C(C)O)SC(CCOP(OP(=O)(O)O)(=O)O)=C1C)C=2C(N)=NC(C)=NC2

Synonyms:

• Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)-, P,P′-dioxide
• Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-
• Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-5-(2-hydroxyethyl)-4-methyl-, 5-(trihydrogen pyrophosphate)
• 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium
• 2-(α-Hydroxyethyl)thiamine diphosphate