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Thiamine diphosphate

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Identification
Molecular formula
C12H19N4O7P2
CAS number
154-87-0
IUPAC name
2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
State
State

At room temperature, thiamine diphosphate is typically found as a solid, crystalline substance. It is often handled in powdered form for its various applications, and should be stored under dry conditions to maintain its stability.

Melting point (Celsius)
248.00
Melting point (Kelvin)
521.15
Boiling point (Celsius)
200.00
Boiling point (Kelvin)
473.15
General information
Molecular weight
426.37g/mol
Molar mass
426.3660g/mol
Density
1.1900g/cm3
Appearence

Thiamine diphosphate, also known as thiamine pyrophosphate, appears as a white to slightly yellow crystalline powder. It is hygroscopic and absorbs moisture from the environment. The compound is stable in dry conditions but may degrade upon prolonged exposure to light and air.

Comment on solubility

Solubility Characteristics of 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate

The solubility of 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate (C12H19N4O7P2) can be attributed to its unique chemical structure, which includes various functional groups that influence its interaction with solvents. Here are some key points to consider:

  • Polarity: The presence of several polar phosphate groups (-OPO₃H₂) enhances the compound's ability to dissolve in polar solvents, particularly water.
  • Hydrogen Bonding: The amino group and the phosphonic acid functionalities can engage in hydrogen bonding with water molecules, further aiding solubility.
  • Solvent Interaction: Although highly soluble in water due to its ionic nature, this compound may have limited solubility in nonpolar solvents like hexane or toluene.
  • pH Dependency: The solubility may also vary with pH: in acidic or neutral pH, the compound may exhibit enhanced solubility due to protonation of the nitrogen atoms.

In summary, the solubility of this phosphoramide compound is primarily influenced by its polar characteristics and the nature of its substituents, which facilitate interactions with polar solvents. This makes it particularly interesting for applications where solubility plays a critical role in chemical reactivity and bioavailability.

Interesting facts

Interesting Facts about 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate

This complex compound possesses a unique structure that incorporates both pyrimidine and thiazole moieties, which contribute to its intriguing biological activity. Here are some fascinating aspects of this compound:

  • Pharmacological Relevance: The compound is a structural derivative related to nucleotides and nucleoside analogs, making it of interest in pharmaceutical research for developing antiviral and anticancer therapies.
  • Enzyme Interaction: It has the potential to interact with various enzymes, particularly those involved in nucleic acid synthesis, affecting cellular processes.
  • Structural Diversity: The presence of both a phosphono group and aromatic heterocycles endows the compound with diverse reactivity and properties, which chemists find appealing for further modifications.
  • Biochemical Pathways: This compound may play a role in modulating key biochemical pathways, influencing processes such as signal transduction and gene expression.
  • Research Applications: Scientists are exploring the compound’s potential use in biotechnology and drug development, especially due to its phosphonate functionalities.

“Understanding the chemical behavior of this compound is crucial for unlocking new therapeutic avenues.”

Given its intricate structure and potential functional benefits, 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate represents a compelling target for further research and innovation in the field of medicinal chemistry.

Synonyms
thiamine diphosphate
136-08-3
ThPP
thiamin diphosphate
thiamin pyrophosphate
ThDP
CHEBI:9532
thiamine-pyrophosphate
Cocarboxylase [INN]
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
thiamine(1+) diphosphate
thiamine-PPi
thiamin-PPi
Pyrophosphoric ester of thiamine
COCARBOXYLASE [MART.]
COCARBOXYLASE [WHO-DD]
DTXSID2048404
3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-((hydroxy(phosphonooxy)phosphoryl)oxy)ethyl)-4-methylthiazol-3-ium
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[4,6,6-trihydroxy-4,6-dioxo-3,5-dioxa-4,6-diph
NCGC00160617-01
Q57971654Y
1ols
1olu
1olx
Thaimine pyrophosphate
1v1m
starbld0000845
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(diphosphooxy)ethyl]-4-methyl-1,3-thiazol-3-ium
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)-
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
SCHEMBL80028
CHEMBL1236376
BDBM92962
1v11
1v16
AYEKOFBPNLCAJY-UHFFFAOYSA-O
AKOS015961391
NCGC00160617-02
NCGC00160617-03
AC-13726
NS00070401
C00068
Q415003
BRD-A09994331-003-02-4
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium