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L-Phenylalanine mustard

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Identification
Molecular formula
C13H18Cl2N2O2
CAS number
51-15-0
IUPAC name
2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic acid
State
State

This compound is typically found in a solid state at room temperature.

Melting point (Celsius)
145.00
Melting point (Kelvin)
418.15
Boiling point (Celsius)
467.20
Boiling point (Kelvin)
740.35
General information
Molecular weight
321.20g/mol
Molar mass
321.2100g/mol
Density
1.3070g/cm3
Appearence

The compound typically appears as a white to off-white crystalline powder.

Comment on solubility

Solubility Insights of 2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic acid

The solubility of 2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic acid, often referred to by its systematic name, can be influenced by various factors. This compound, which contains both hydrophilic and hydrophobic features, exhibits interesting solubility behavior:

  • Polar Groups: The presence of amino and carboxylic acid functional groups enhances its solubility in polar solvents, such as water.
  • Hydrophobic Regions: Conversely, the bis(2-chloroethyl)amino moiety introduces hydrophobic characteristics, which may hinder solubility in aqueous environments.
  • pH Dependence: The solubility can also be affected by the pH of the solution. In basic conditions, the carboxylic acid may deprotonate, increasing its solubility.
  • Temperature Effects: Generally, increasing temperature can lead to an increase in solubility, although this can vary based on specific solvent interactions.

Overall, the solubility profile of this compound emphasizes the balance between its polar and nonpolar characteristics. Understanding these aspects is crucial for its application in various chemical processes.

Interesting facts

Interesting Facts About 2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic Acid

This compound is a fascinating example of a highly functionalized amino acid that exhibits significant biological activity. Its structure includes a classic amino acid backbone, which is modified by the presence of a bis(2-chloroethyl)amino group, known for its role in medicinal chemistry, particularly as a cytotoxic agent.

Key Features:

  • Biodiversity in Structure: The unique configuration of this compound allows it to interact with various biological targets. This intricate arrangement of substituents makes it relevant in the study of drug design.
  • Medicinal Properties: Derivatives of this compound have been researched for their potential use in chemotherapy, as the bis(2-chloroethyl) group can facilitate alkylation, leading to DNA damage in cancer cells.
  • Synthetic Pathways: The synthesis of 2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic acid involves multi-step reactions that illustrate the creativity required in organic synthesis. It showcases the art of building complex molecules from simpler ones.
  • Research Applications: Scientists are investigating its role in the development of novel therapeutic agents, making it a significant compound in ongoing cancer research.

In conclusion, the utility of 2-amino-3-[2-[bis(2-chloroethyl)amino]phenyl]propanoic acid extends beyond its basic chemical structure. It stands as a testament to the connection between chemistry and medicine, highlighting the ongoing quest for effective treatments in oncology. As we delve deeper into the realms of chemical compounds like this, we uncover potential solutions to some of the most pressing challenges in healthcare.

Synonyms
Merophan
o-Merphalan
o-DL-Sarcolysin
o-Phenylalanine mustard
(+-)-O-Phenylalanine mustard
FDA 0109
342-95-0
3-(o-(Bis(beta-chloroethyl)amino)phenyl)-D,L-alanine
NSC-57199
CB 1729
2-[bis(2-chloroethyl)amino]phenylalanine
2-(bis(2-Chloroethyl)amino)phenylalanine
DL-Phenylalanine, 2-(bis(2-chloroethyl)amino)-
DL-Alanine, 3-(o-(bis(2-chloroethyl)amino)phenyl)-
o-Sarcolysin
Ortho-phenylalanine mustard
DL-Phenylalanine, 2-[bis(2-chloroethyl)amino]-
DL-Alanine, 3-(o-[bis(2-chloroethyl)amino]phenyl)-
o-Di-2-chloroethylamino-DL-phenylalanine
AI3-50754
D,L-Sarcolysin
3-(o-(Bis(beta-chloroethyl)amino)phenyl)-DL-alanine
ALANINE, 3-(o-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-, DL-
NCIOpen2_007587
WLN: QVYZ1R BN2G2G
CHEMBL3247486
(.+-.)-o-Phenylalanine mustard
DTXSID801273943
NCI-C04944
NSC57199
DS-001019
o-Di-(2-chloroethyl)amino-DL-phenylalanine
Phenylalanine, 2-(bis(2-chloroethyl)amino)-
3-(o-(Bis(.beta.-chloroethyl)amino)phenyl)-d,l-alanine
3-[o-[Bis(.beta.-chloroethyl)amino]phenyl]-DL-alanine