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L-DOPA

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Identification
Molecular formula
C9H11NO4
CAS number
59-92-7
IUPAC name
2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
State
State
At room temperature, L-DOPA is a solid, typically found as a crystalline powder.
Melting point (Celsius)
295.00
Melting point (Kelvin)
568.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
197.19g/mol
Molar mass
197.1880g/mol
Density
1.6800g/cm3
Appearence
L-DOPA appears as a white to off-white crystalline powder. It is slightly soluble in water and has a slightly bitter taste.
Comment on solubility

Solubility of 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, with the chemical formula C9H11NO4, is known for its intriguing solubility properties influenced by both its structure and functional groups. This compound contains polar functional groups such as amino (-NH2) and hydroxyl (-OH) groups, which significantly enhance its interaction with water molecules.

The solubility characteristics can be summarized as follows:

  • High solubility in water: The presence of multiple hydroxyl groups tends to promote solvation in polar solvents, particularly water.
  • Possible solubility in organic solvents: Depending on the solvent polarity, this compound may exhibit varying degrees of solubility in organic solvents, although it’s primarily hydrophilic.
  • Temperature effects: Like many organic compounds, its solubility may increase with temperature due to enhanced kinetic energy that aids in breaking intermolecular interactions.

In conclusion, as with many compounds bearing hydroxyl and amino groups, 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid showcases a tendency to be soluble in aqueous solutions, making it a versatile compound in various biochemical contexts.

Interesting facts

Interesting Facts about 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, often referred to as a derivative of tyrosine, is a fascinating compound with numerous implications in both biology and chemistry.

Key Characteristics

  • Amino Acid Structure: This compound functions as an amino acid, which is crucial for protein synthesis and various metabolic pathways.
  • Bioactivity: It is a key precursor to neurotransmitters and plays a significant role in the biosynthesis of catecholamines, which are vital for brain function and emotional regulation.

Applications and Importance

  • Health Supplement: Due to its structural similarity to L-tyrosine, this compound is considered for use in dietary supplements aimed at improving cognitive functions.
  • Research Tool: It is utilized in various biochemical research studies to investigate the molecular mechanisms of neurotransmitter synthesis.
  • Potential Therapeutics: There is ongoing research into its potential roles in treating conditions such as Parkinson's disease and depression by modulating neurotransmitter levels.

Chemical Interactions

The presence of hydroxyl groups in its structure can lead to significant interactions in biological systems, enhancing its functionality and reactivity. This property allows it to participate in various enzymatic reactions, making it an interesting subject of study for medicinal chemists.

Quote

As the famous chemist Linus Pauling once said, "The nature of a chemical bond is the most important aspect of chemistry." In the case of 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, its unique bonds and functional groups indeed highlight its importance in the understanding of biochemical processes.

In summary, 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid is not just another organic compound; it represents a vital intersection of chemistry, biology, and medicine, illustrating how intricate and fascinating chemical compounds can be.

Synonyms
DL-DOPA
63-84-3
3,4-Dihydroxy-DL-phenylalanine
2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
3-(3,4-Dihydroxyphenyl)-DL-alanine
dihydroxyphenylalanine
3-Hydroxytyrosine
DL-Dihydroxyphenylalanine
DL-Dioxyphenylalanine
DL-Tyrosine, 3-hydroxy-
3-Hydroxy-DL-tyrosine
DL-3,4-Dopa
DL-3-Hydroxytyrosine
(R,S)-Dopa
(+-)-Dopa
3',4'-Dihydroxyphenylalanine
DL-beta-(3,4-Dihydroxyphenyl)alanine
D-Tyrosine, 3-hydroxy-
EINECS 200-566-0
MFCD00063060
NSC 16940
(+-)-3-(3,4-Dihydroxyphenyl)alanine
AI3-23874
Tyrosine, 3-hydroxy-
3 Hydroxy DL tyrosine
QI9C343R60
NSC-16940
DOPA, DL-
2-amino-3-(3,4-dihydroxy-phenyl)-propionic acid
DTXSID8020549
CHEBI:49168
ALANINE, 3-(3,4-DIHYDROXYPHENYL)-, DL-
D-B-3,4-Dihydroxyphenylalanine
D-3-Hydroxytyrosine
beta Hydroxytyrosine
dl-3,4-Dihydroxyphenylalanine
WLN: QVYZ1R CQ DQ
3,4 Dihydroxyphenylalanine
UNII-QI9C343R60
3-(3,4-Dihydroxyphenyl)-D-alanine
3HydroxyDLtyrosine
DL3Hydroxytyrosine
DLDioxyphenylalanine
beta-(3,4-Dihydroxyphenyl)-alpha-alanine
DLDOPA
DLTyrosine, 3hydroxy
DL3,4Dopa
DOPA DL-FORM
3,4DihydroxyDLphenylalanine
DOPA DL-FORM [MI]
SCHEMBL24360
alpha-amino-Hydrocaffeic acid
(.+-.)-Dopa
3,4-Dihydroxyphenylalanine #
DTXCID00549
DL-4,5-Dihydroxyphenylalanine
BDBM4377
CHEMBL351042
3(3,4Dihydroxyphenyl)DLalanine
DL-DOPA; DL-Dioxyphenylalanine
D-Tyrosine, 3-hydroxy-(9CI)
Alanine,4-dihydroxyphenyl)-, D-
DL-3',4'-Dihydroxyphenylalanine
3(3,4-Dihydroxyphenyl)dl-alanine
DLbeta(3,4Dihydroxyphenyl)alanine
Alanine,4-dihydroxyphenyl)-, DL-
BCP25747
NSC16940
b-(3,4-Dihydroxyphenyl)-a-alanine
DL-b-(3,4-Dihydroxyphenyl)alanine
BBL010087
NSC118368
STK801445
(.+-.)-3,4-Dihydroxyphenylalanine
AKOS001132704
AKOS016843592
Alanine, 3(3,4dihydroxyphenyl), DL
3,4-Dihydroxy-DL-phenylalanine, 97%
FD58239
GS-6861
PB43103
a-amino-3,4-dihydroxy-Benzenepropanoate
L-dopa; 3,4-Dihydroxy-L-phenylalanine
NCGC00015384-02
NCGC00015384-03
NCGC00095195-01
NCGC00095195-02
(+/-) 3-(3,4-Dihydroxyphenyl)alanine
AS-81574
BP-12841
DL-.beta.-(3,4-Dihydroxyphenyl)alanine
SY010977
SY343921
(.+-.)-3-(3,4-Dihydroxyphenyl)alanine
DL-Alanine, 3-(3,4-dihydroxy-phenyl)-
(+/-)-3,4-DIHYDROXYPHENYLALANINE
2-Amino-3-(3,4-dihydroxyphenyl)propanoate
alpha-amino-3,4-dihydroxy-Benzenepropanoate
DB-053498
HY-113404
a-amino-3,4-dihydroxy-Benzenepropanoic acid
CS-0059346
D0599
D9503
dl-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
NS00006424
S6083
beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanine
EN300-52489
2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate
alpha-amino-3,4-dihydroxy-Benzenepropanoic acid
H11952
.beta.-(3,4-Dihydroxyphenyl)-DL-.alpha.-alanine
AH-034/32470039
L001274
(2-Pyrrolidin-3-yl-ethyl)-carbamic acid benzyl ester
Q27121510
DD916368-6635-446F-AF55-7B416FD65026
IM3