54732-46-6

Basic information

• Product Name: (S)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID
• Synonyms: H-BETA-PHE(4-OH)-OH;H-D-PHG(4-OH)-(C*CH2)OH;RARECHEM LK HW 0163;(S)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID;H-b-Phe(4-OH)-OH;H-β-Phe(4-OH)-OH;(3S)-3-Amino-3-(4-hydroxyphenyl)propanoic acid
• CAS NO: 54732-46-6
• Molecular Formula: C₉H₁₁NO₃*ClH
• Molecular Weight: 181.19
• Product Categories: B-Amino
• Mol File: 54732-46-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (S)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID(54732-46-6)
• EPA Substance Registry System: (S)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID(54732-46-6)

Safety Data

• Hazardous Substances Data: 54732-46-6(Hazardous Substances Data)

Usage

General Description

"(S)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid, also referred to as Tyrosine in its biochemical form, is a chemical compound with the molecule formula C9H11NO3. Being an alpha-amino acid, it is utilized in the biosynthesis of proteins. The (S)-3-Amino-3-(4-hydroxy-phenyl)-propionic acid is comprised of a Benzyl group, which has a phenol substituent at the para position. Its 'S' descriptor denotes that it is the 'left-handed' isomer of this molecule, which is important for its natural biological activity. This chemical compound is typically involved in various chemical reactions, especially in the medical and biological fields, including the production of neurotransmitters and enzymes. It can also act as a precursor for the synthesis of several important molecules, such as melanin and thyroid hormones.

InChI:InChI=1/C9H11NO3.ClH/c10-8(5-9(12)13)6-1-3-7(11)4-2-6;/h1-4,8,11H,5,10H2,(H,12,13);1H/t8-;/m0./s1

Upstream product

• 177966-65-3 methyl (3S)-3-amino-3-(4-hydroxyphenyl)propanoate 
• 134430-96-9 (S)-β-tyrosine methyl ester hydrochloride 
• 84184-51-0 (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate 
• 134430-95-8 methyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoate 

Relevant articles and documents

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.