73025-68-0

Basic information

• Product Name: (R)-4-HYDROXY-BETA-PHENYLALANINE
• Synonyms: (R)-4-HYDROXY-BETA-PHENYLALANINE;(R)-3-Amino-3-(4-hydroxyphenyl)propionic acid;D-3-Amino-3-(4-hydroxyphenyl)propanoic acid
• CAS NO: 73025-68-0
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Mol File: 73025-68-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 220-221 °C
• Boiling Point: 378.7 °C at 760 mmHg
• Flash Point: 182.9 °C
• Appearance: /
• Density: 1.329 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.76±0.10(Predicted)
• CAS DataBase Reference: (R)-4-HYDROXY-BETA-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-HYDROXY-BETA-PHENYLALANINE(73025-68-0)
• EPA Substance Registry System: (R)-4-HYDROXY-BETA-PHENYLALANINE(73025-68-0)

Safety Data

• Hazardous Substances Data: 73025-68-0(Hazardous Substances Data)

Usage

General Description

(R)-4-Hydroxy-beta-phenylalanine, also known as D-phenylalanine, is an amino acid that is naturally occurring and essential for the body. It plays a crucial role in the production of proteins and neurotransmitters. It is also a precursor to the neurotransmitters dopamine, norepinephrine, and epinephrine, which are important for mood regulation, energy levels, and focus. Additionally, (R)-4-Hydroxy-beta-phenylalanine has been studied for its potential therapeutic effects in the management of chronic pain and depression. It is also commonly used as a nutritional supplement to support overall well-being and mental health.

Upstream product

• 329013-03-8 3-(4-hydroxy-phenyl)-3-phenylacetylamino-propionic acid 
• 166023-23-0 (R)-3-amino-3-(4-hydroxyphenyl)propionic acid tert-butyl ester 
• 691905-29-0 tert-butyl (E)-3-(4-benzyloxyphenyl)propenoate 
• 951174-28-0 tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoate 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 499995-80-1 C₁₄H₁₉NO₅ 
• 329013-12-9 (S)-N-tert-butyloxycarbonyl β-Tyr 

Downstream Products

• 329013-12-9 (S)-N-tert-butyloxycarbonyl β-Tyr 
• 1448510-86-8 4'-O,3-N-((2S)-methylbutyryl)ethyl ester 
• 177966-66-4 (R)-β-tyrosine methyl ester 

Relevant articles and documents

Resolution synthesis method of 3-amino-3-(4-hydroxyphenyl)propionic acid

The invention relates to a resolution synthesis method of 3-amino-3-(4-hydroxyphenyl)propionic acid, mainly aiming at solving the technical problems of an existing synthesis method of more steps and high cost. The resolution synthesis method comprises the following steps: enabling p-hydroxybenzaldehyde to react with ammonium acetate and malonic acid in an ethanol solution to generate a compound 1; enabling the compound 1 to react with triethylamine and di-tert-butyl dicarbonate in a mixed solution of water and acetone to generate a compound 2; enabling the compound 2 to react with R(+)-1-phenethylamine in a tetrahydrofuran solution; acidifying an intermediate product with hydrochloric acid to generate a compound 3; enabling the compound 3 to react with an ethanol solution of hydrochloric acid to obtain hydrochloride, and enabling the hydrochloride to react with a sodium hydroxide water solution to obtain a target compound 4; enabling the compound 2 to react with S-1-phenethylamine in the tetrahydrofuran solution, and acidifying an intermediate product with the hydrochloric acid to generate a compound 5; enabling the compound 5 to react with the ethanol solution of the hydrochloric acid to obtain hydrochloride and enabling the hydrochloride to react with a sodium hydroxide water solution to obtain a target compound 6. (R)- and (S)-3-amino-3-(4-hydroxyphenyl)propionic acid is widely applied in a polypeptide biopharmaceutical industry.

Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.