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Levodopa methyl ester

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Identification
Molecular formula
C11H15NO4
CAS number
17611-60-4
IUPAC name
methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate
State
State

At room temperature, levodopa methyl ester is in a solid state. It should be stored in a cool, dry place away from direct sunlight and moisture to maintain its stability.

Melting point (Celsius)
103.00
Melting point (Kelvin)
376.15
Boiling point (Celsius)
320.00
Boiling point (Kelvin)
593.15
General information
Molecular weight
241.27g/mol
Molar mass
241.2720g/mol
Density
1.3715g/cm3
Appearence

Levodopa methyl ester is typically a white to off-white crystalline powder. It is sensitive to air and light, which can cause it to change in color over time if not properly stored.

Comment on solubility

Solubility of Methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate

The solubility of methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate is influenced by several factors due to its complex structure. Generally, this compound exhibits some notable solubility characteristics:

  • Water Solubility: This compound shows a moderate level of solubility in water, largely attributed to the presence of the amino and hydroxyl groups that can engage in hydrogen bonding with water molecules.
  • Organic Solvents: It is more soluble in organic solvents such as ethanol and methanol, which can stabilize its hydrophobic regions, further enhancing its solubility in these environments.

Moreover, the presence of the 3,4-dihydroxyphenyl group introduces additional polar character, which can increase solubility in polar solvents. It's crucial to note that:

  1. The structural polarity derived from the amino and hydroxyl functional groups aids in the dissolution process.
  2. Temperature can also play a role; generally, as temperature increases, solubility tends to improve.

To summarize, the solubility of methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate can be classified as:

  • Moderately soluble in water
  • Highly soluble in ethanol and similar organic solvents

The interplay of hydrophilic and hydrophobic interactions makes it essential to consider the solvent environment when evaluating the solubility of such compounds.

Interesting facts

Interesting Facts about Methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate

Methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate, commonly referred to as a derivative of phenylalanine, is a fascinating compound within the realm of biochemistry. Here are several intriguing aspects of this compound:

  • Amino Acid Parentage: This compound is a methyl ester of an amino acid, which underscores its role as a building block of proteins. Amino acids are vital for various biological functions and processes.
  • Phenolic Compound Influence: The presence of the 3,4-dihydroxyphenyl group binds this compound to the class of phenolic compounds, which are widely studied for their antioxidant properties. Antioxidants play a crucial role in protecting the body from oxidative stress and cellular damage.
  • Enantiomer Specificity: The (2S) designation indicates that this compound is one enantiomer of a chiral molecule, which means it may interact differently with biological systems compared to its mirror image, highlighting the importance of chirality in drug design and metabolism.
  • Applications in Medicine: Methyl esters of amino acids are often utilized in peptide synthesis, which is essential for developing pharmaceuticals. This specific compound could serve as a precursor in the synthesis of bioactive peptides or pharmaceuticals, showcasing the interconnectivity of chemistry and medicine.
  • Research Potential: The study of methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate has implications in nutritional science due to its potential effects on metabolic pathways and human health.

As a student or scientist, understanding the chemistry of such compounds encourages a deeper appreciation for how seemingly simple structures can have profound effects in biological systems. As you delve into the world of amino acids and their derivatives, remember: "Every compound has a story, waiting to be explored."

Synonyms
methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
49ARC1V0F1
CARBIDOPA IMPURITY B [EP IMPURITY]
3-Hydroxy-alpha-methyl-L-tyrosine methyl ester
CARBIDOPA IMPURITY B (EP IMPURITY)
Alpha-methyl-melevodopa
.ALPHA.-METHYL-MELEVODOPA
3-HYDROXY-ALPHA-METHYL-METHYL TYROSINATE
3-HYDROXY-.ALPHA.-METHYL-METHYL TYROSINATE
895-229-3
18181-08-3
alpha-Methyldopa methyl ester
alpha-Methyl-3,4-dihydroxy-L-phenylalanine methyl ester
a-Methyldopa Methyl Ester
Methyl (S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
158190-23-9
BRN 2649505
Methyl (2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoate; 3-Hydroxy-a-methyl-L-tyrosine Methyl Ester; Alanine, 3-(3,4-dihydroxyphenyl)-2-methyl-, methyl ester, L- (8CI); a-Methyldopa Methyl Ester
L-3-(3,4-Dihydroxyphenyl)-2-methylalanine methyl ester
starbld0004048
Carbidopa EP Impurity B
?-Methyldopa methyl ester
ALANINE, 3-(3,4-DIHYDROXYPHENYL)-2-METHYL-, METHYL ESTER, L-
UNII-49ARC1V0F1
L-Tyrosine, 3-hydroxy-alpha-methyl-, methyl ester
SCHEMBL1485976
SCHEMBL29881847
DTXSID90939476
FM30422
Methyl 3-hydroxy-alpha-methyltyrosinate
EN300-1070266