3-(3-Hydroxyphenyl)-DL-alanine
[CAS# 775-06-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Tyrosine derivatives
• Name: 3-(3-Hydroxyphenyl)-DL-alanine
• Synonyms: DL-m-Tyrosine; (+/-)-2-Amino-3-(3-hydroxyphenyl)propionic acid
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Protein Sequence: X
• CAS Registry Number: 775-06-4
• EC Number: 212-270-9
• SMILES: C1=CC(=CC(=C1)O)CC(C(=O)O)N

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 280 - 285 °C (Decomposes) (Expl.)
• Boiling point: 387.2±32.0 °C 760 mmHg (Calc.)^*
• Flash point: 188.0±25.1 °C (Calc.)^*
• Index of refraction: 1.614 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: Pictogram(s)
• Risk Statements: R36/37/38
• Safety Statements: S26;S37/39

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-(3-Hydroxyphenyl)-DL-alanine is a synthetic amino acid derivative characterized by the presence of a hydroxy-substituted phenyl group attached to the beta carbon of alanine. This compound exists as a racemic mixture, containing both D- and L-enantiomers, reflecting the mirror-image forms of the molecule.

The discovery of 3-(3-hydroxyphenyl)-DL-alanine is linked to the broader exploration of amino acid analogs designed to study structure-activity relationships and enzyme specificity. Its structural similarity to naturally occurring amino acids makes it a useful tool in biochemical and pharmacological research.

This compound is utilized primarily in the study of enzymes that interact with aromatic amino acids, such as tyrosine hydroxylase and related pathways in neurotransmitter biosynthesis. Its hydroxyphenyl moiety resembles that of tyrosine, enabling it to serve as a substrate analog or inhibitor in enzymatic assays.

In addition to enzyme studies, 3-(3-hydroxyphenyl)-DL-alanine is used in peptide synthesis to introduce specific functional groups into peptides or proteins. The hydroxy group can participate in hydrogen bonding and metal coordination, which can influence the biological activity and structural properties of peptides containing this residue.

The racemic nature of the compound allows for investigation of stereochemical effects on biological activity. Differences in the behavior of the D- and L-forms provide insights into enzyme stereospecificity and receptor interactions.

In medicinal chemistry, derivatives of 3-(3-hydroxyphenyl)-DL-alanine have been explored for their potential as therapeutic agents or enzyme inhibitors. Modifications of the hydroxyphenyl group or the amino acid backbone can lead to compounds with enhanced biological properties or specificity.

Overall, 3-(3-hydroxyphenyl)-DL-alanine serves as an important molecular tool in biochemical research, enabling the study of aromatic amino acid metabolism, enzyme function, and peptide modification. Its use contributes to a deeper understanding of biochemical pathways and supports the development of novel therapeutic compounds.

References

1974. Aterial blood pressure in dogs: effects of m-tyrosine alone or in combination with inhibitors of aromatic amino acid decarboxylase; relative hypotensive potencies of L-dopa, DL-m-tyrosine, and L-m-tyrosine. Cellular and Molecular Life Sciences, 30(9).
DOI: 10.1007/bf01939004

1997. Biochemistry of the Sulfation of Dopa and Tyrosine Isomers. Animal Cell Technology: Basic & Applied Aspects.
DOI: 10.1007/978-94-011-5746-9_49

2010. From sepiamelanin to chemical ecology of opisthobranchs and diatoms: an exciting 40 years game in the field of marine natural products. Phytochemistry Reviews, 9(4).
DOI: 10.1007/s11101-010-9199-4