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5-Fluoro-DL-tryptophan

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Identification
Molecular formula
C11H11FN2O2
CAS number
327-97-9
IUPAC name
2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
State
State

At room temperature, 5-Fluoro-DL-tryptophan is a solid compound, typically handled as a crystalline powder.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.15
Boiling point (Celsius)
333.30
Boiling point (Kelvin)
606.45
General information
Molecular weight
214.21g/mol
Molar mass
214.1980g/mol
Density
1.4230g/cm3
Appearence

5-Fluoro-DL-tryptophan is a white to off-white crystalline powder. It is relatively stable under standard conditions, but may decompose if exposed to light or heat over time.

Comment on solubility

Solubility of 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid

The solubility of 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid, also known as a derivative of amino acids, can be influenced by a variety of factors. Notably, this compound exhibits notable solubility characteristics due to its structural components:

  • Polarity: The presence of the amino group (-NH2) and the carboxylic acid group (-COOH) contribute to the polarity of the molecule, enhancing its affinity for polar solvents like water.
  • Interactions: This compound can engage in hydrogen bonding with water molecules, which significantly improves its solubility.
  • Fluoro substitution: The -F group can also impact the compound's overall electronic properties, potentially altering its solubility in various organic solvents.

In general terms, amino acids are typically highly soluble in water, and the presence of additional functional groups in this specific compound likely elevates its solubility profile. However, precise solubility measurements can vary depending on temperature, pH, and the presence of other solutes in the solvent system.

In conclusion, one might say this compound, owing to its structural features, is expected to have an enhanced solubility in polar solvents, making it interesting for further biochemical and pharmaceutical applications.

Interesting facts

Interesting Facts about 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid

2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid, often abbreviated as ADF, is a fascinating chemical compound due to its unique structure and potential applications in various fields. Here are some intriguing aspects:

  • Biological Role: This compound can act as an analog of amino acids, playing a significant role in biochemical processes. Compounds similar to ADF have the potential to interfere with neurotransmitter functions, affecting mood and behavior.
  • Fluorine's Influence: The presence of fluorine in ADF is particularly interesting. Fluorine, when incorporated into organic molecules, significantly enhances the compound's metabolic stability and lipophilicity. This can lead to more effective drugs with longer half-lives in the body.
  • Indole Derivative: ADF contains an indole ring system, which is vital in medicinal chemistry. Indole derivatives are known for their diverse biological activities, including anti-cancer properties and roles as enzyme inhibitors.
  • Research Potential: Due to its distinct features, ADF is a subject of ongoing research in the field of drug discovery and development. Scientists are keen to investigate how modifications to the indole structure can lead to new therapeutic agents.
  • Synthesis Techniques: The synthesis of ADF can involve various chemical reactions, such as nucleophilic substitution and amino acid coupling. These processes not only demonstrate important concepts in organic chemistry but also highlight the creativity required in chemical synthesis.

With its combination of amino acid properties, indole structure, and the influence of fluorine, 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid exemplifies how subtle changes in molecular structure can lead to significant shifts in function, making it a prime candidate for further scientific exploration.

Synonyms
5-Fluoro-dl-tryptophan
154-08-5
5-FLUOROTRYPTOPHAN
2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
DL-5-Fluorotryptophan
Tryptophan, 5-fluoro-
Tryptophan, 5-fluoro-, DL-
5-fluoro-d,l-tryptophan
EINECS 205-822-5
BRN 0022753
5IC9663SHW
343-91-9
NSC-9363
DL-Tryptophan, 5-fluoro-
5-FLUOROTRYPTOPHAN, DL-
5-22-14-00116 (Beilstein Handbook Reference)
1,1-Diphenyldiazomethane (>90%)
NSC 9363
CHEBI:77837
DTXSID20870489
UNII-5IC9663SHW
Diazodiphenylmethane; Diphenylazomethane; Diphenyldiazomethane
MFCD00005649
5-Fluoro D,L-tryptophan
SCHEMBL125000
5-Fluoro-DL-tryptophan, powder
CHEMBL5175188
NSC9363
DL-5-Fluorotryptophan;NSC 9363
AKOS002663102
AKOS016042907
CS-W013117
FF23354
PS-6615
NS00041522
A50268
SR-01000003308
SR-01000003308-1
Q27147445
DL-2-Amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid