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

• 65451-19-6 N-(phenylacetyl)-3-amino-3-phenylpropanoic acid 
• 5661-55-2 4-phenylazetidin-2-one 
• 63-91-2 L-phenylalanine 
• 40638-98-0 (R/S)-3-(acetylamino)-3-phenylpropanoic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 717137-43-4 (4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one 
• 100-52-7 benzaldehyde 
• 1426822-57-2 C₁₃H₁₄F₃NO₃ 
• 67654-57-3 methyl (R)-3-acetamido-3-phenylpropanoate 
• 3082-68-6 (R)-3-amino-3-phenylpropionic acid ethyl ester 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 29754-04-9 ethyl 3-amino-3-phenylpropanoate hydrochloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 144494-74-6 (R)-3-benzamido-3-phenylpropanoic acid methyl ester 
• 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 
• 1050324-77-0 (R)-3-phenyl-3-(2,2,2-trifluoroacetamido)propanoic 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 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 82359-85-1 C₁₅H₂₇NO₂Si₂ 
• 37088-64-5 (S)-4-phenyl-2-azetidinone 
• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 22839-32-3 Benzyloxycarbonyl-L-β-amino-β-phenyl-propionyl-L-α-amino-buttersaeuremethylester 
• 1117977-25-9 C₂₄H₁₉Cl₄NO₅ 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 

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.

Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids

A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatography, and its biochemical properties were studied. The HpN was very stable at 30–40?°C, and highly active over a wide range of pH values (pH 6.0–10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a KM of 4.2?mM and a kcat of 170?s?1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73–99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.

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.