614-19-7

Basic information

• Product Name: 3-Amino-3-phenylpropionic acid
• Synonyms: 2-Amino-2-phenylpropansαure;Benzenepropanoicacid,βamino-;Benzenepropanoicacid,β-amino-,(±)-;DL-3-Amino-3-phenylpropionsαure;DL-Aminohydrocinnamicacid;DL-β-Phe-OH;R,S-3-Amino-3-phenyl-propionicacid;β-Aminohydrocinnamicacid
• CAS NO: 614-19-7
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 210-371-2
• Product Categories: Benzene series;Amino Acids and Derivatives;Organic acids;B-Amino;Pyridines
• Mol File: 614-19-7.mol
• Article Data: 69

Chemical Properties

• Melting Point: 222 °C (dec.)(lit.)
• Boiling Point: 293.03°C (rough estimate)
• Flash Point: 139.8 °C
• Appearance: white crystalline powder
• Density: 1.1603 (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.45±0.12(Predicted)
• Water Solubility: SOLUBLE
• BRN: 2803286
• CAS DataBase Reference: 3-Amino-3-phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-3-phenylpropionic acid(614-19-7)
• EPA Substance Registry System: 3-Amino-3-phenylpropionic acid(614-19-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-37/39
• WGK Germany: 3
• Hazardous Substances Data: 614-19-7(Hazardous Substances Data)

Usage

Description

3-Amino-3-phenylpropionic acid, also known as DL-β-Phenylalanine, is an organic compound that serves as a valuable synthetic intermediate in the pharmaceutical industry. It is characterized by its unique structure, which includes an amino group and a phenyl ring attached to a propionic acid chain.

Uses

Used in Pharmaceutical Industry:
3-Amino-3-phenylpropionic acid is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be incorporated into a wide range of drug molecules, enhancing their therapeutic properties.
Used in Platelet Aggregation Inhibitors:
3-Amino-3-phenylpropionic acid is used as a key component in the synthesis of platelet aggregation inhibitors. These inhibitors play a crucial role in preventing blood clot formation, which can lead to life-threatening conditions such as heart attacks and strokes.
Used in Human Gonadotropin-Releasing Hormone Receptor Antagonists:
3-Amino-3-phenylpropionic acid is also used as a reagent in the synthesis of human gonadotropin-releasing hormone (GnRH) receptor antagonists. These antagonists are important in the treatment of various hormonal disorders, including endometriosis, uterine fibroids, and certain types of cancer.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 27, p. 2223, 1979 DOI: 10.1248/cpb.27.2223

InChI:InChI=1/C9H11NO2/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

Upstream product

• 63-91-2 L-phenylalanine 
• 112545-23-0 N-(R)-α-Methylbenzyl-(S)-3-phenylisoxazolidin-5-one 
• 850011-53-9 3-formylamino-3-phenyl-propionic acid ethyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 5661-55-2 4-phenylazetidin-2-one 
• 150-30-1 Phenylalanine 
• 100-52-7 benzaldehyde 
• 607737-27-9 3-(2-chloro-acetylamino)-3-phenyl-propionic acid 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 135383-44-7 5-Chloro-3-phenyl-2-((R)-1-phenyl-ethyl)-isoxazolidine-5-carbonitrile 
• 127001-34-7 N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 14990-09-1 tert-butyl cinnamate 
• 65451-19-6 N-(phenylacetyl)-3-amino-3-phenylpropanoic acid 

Downstream Products

• 94099-69-1 (R)-3-dimethylamino-3-phenylpropionic acid 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 117020-31-2 (R)-N-acetyl-3-amino-3-phenylpropionic acid 
• 220498-02-2 (R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid 
• 83649-48-3 (R)-3-amino-3-phenylpropionic acid hydrochloride 
• 37088-67-8 methyl (3R)-3-amino-3-phenylpropanoate 
• 170564-98-4 (R)-3-amino-3-phenyl-1-propanol 
• 1059185-90-8 (S)-3-{[(isopropylamino)carbonyl]amino}-3-phenylpropanoic acid 
• 1117977-25-9 C₂₄H₁₉Cl₄NO₅ 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 56-41-7 L-alanin 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 127413-52-9 (S)-3-benzamido-3-phenylpropanoic acid 
• 1150560-58-9 methanesulfonic acid (S)-3-tert-butoxycarbonylamino-3-phenylpropyl ester 

Relevant articles and documents

Preparation methods of beta-azido acid and beta-amino acid compounds and application thereof

The invention discloses a preparation method of beta-azido acid, which comprises the following step of: carrying out a reaction on an ethylene compound, CZ1Z2Z3Z4 and trimethylsilyl azide as initial raw materials to obtain the beta-azido acid. The ethylene compound has a structural general formula as shown in a formula I, and the beta-azido acid has a structural general formula as shown in a formula II, wherein R is selected from one of alkyl, substituted alkyl, heteroaryl and substituted heteroaryl; and Z1, Z2, Z3 and Z4 are respectively and independently at least one selected from fluorine, chlorine, bromine and iodine. The invention further provides beta-amino acid and application of the preparation method. The preparation methods of the beta-azido acid and the beta-amino acid, provided by the invention, have the advantages of cheap raw materials and catalysts, mild reaction conditions, simplicity in operation, high reaction efficiency and the like.

Β-phenylalanine ester synthesis from stable β-keto ester substrate using engineered ω-transaminases

The successful synthesis of chiral amines from ketones using ω-transaminases has been shown in many cases in the last two decades. In contrast, the amination of β-keto acids is a special and relatively new challenge, as they decompose easily in aqueous solution. To avoid this, transamination of the more stable β-keto esters would be an interesting alternative. For this reason, ω-transaminases were tested in this study, which enabled the transamination of the β-keto ester substrate ethyl benzoylacetate. Therefore, a ω-transaminase library was screened using a coloring o-xylylenediamine assay. The ω-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-β-phenylalanine esters. This alternative approach resulted in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-β-phenylalanine ethyl ester was isolated by performing a semi-preparative synthesis.

Synthetic method for novel chiral ligand, metal chelate, multiple unnatural amino acids, maraviroc and key intermediate thereof

The invention discloses a synthetic method for a novel chiral ligand, a metal chelate, multiple unnatural amino acids, maraviroc and a key intermediate thereof. According to the synthetic method, (R)-2-methylproline is selected as a starting material, and asymmetrical resolution is induced by utilizing a nickel chelate, so that (S)-beta3-amino acid is obtained, and (S)-3-amino-3-phenylpropionic acid is taken as the key intermediate for synthesizing maraviroc, so that yield is high, and ee value reaches more than or equal to 98.2%. The method disclosed by the invention has the advantages that source of raw materials is wide, conditions of a synthetic process are mild, control is easy, and optical purity of products is high.