131690-57-8

Basic information

• Product Name: (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID
• Synonyms: (R)-BETA-(P-METHOXYPHENYL)ALANINE;(R)-B-(P-METHOXYPHENYL)-B-ALANINE;(R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID;L-BETA-HOMO(4-METHOXYPHENYL)GLYCINE;H-PHG(4-OME)-(C*CH2)OH;H-D-BETA-PHE(4-OME)-OH;(R)--(p-Methoxyphenyl)alanine;(R)-3-(P-METHOXYPHENYL)-BETA-ALANINE
• CAS NO: 131690-57-8
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• Mol File: 131690-57-8.mol

Chemical Properties

• Boiling Point: 356.391 °C at 760 mmHg
• Flash Point: 169.339 °C
• Appearance: /
• Density: 1.206 g/cm³
• Vapor Pressure: 1.07E-05mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID(131690-57-8)
• EPA Substance Registry System: (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID(131690-57-8)

Safety Data

• Hazardous Substances Data: 131690-57-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID is used as a building block for the synthesis of various pharmaceuticals and bioactive molecules. Its unique structure and functional groups make it a valuable component in the creation of new drugs and therapeutic agents.
Used in Research and Development:
In the field of neurobiology and central nervous system studies, (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID serves as a crucial tool for understanding the mechanisms of action and potential applications of various compounds. Its involvement in these studies aids in the advancement of knowledge and the development of novel treatments for neurological disorders.
Used in Pain Management:
(R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID is known to exhibit analgesic properties, making it a potential candidate for the treatment of pain. Its ability to alleviate pain may be attributed to its interaction with specific receptors or pathways in the body, providing relief to patients suffering from various types of pain.
Used in Inflammatory Conditions Treatment:
Due to its anti-inflammatory properties, (R)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID can be utilized in the management of inflammatory conditions. Its capacity to reduce inflammation may be beneficial in treating a range of conditions, from minor injuries to chronic inflammatory diseases, by modulating the immune response and mitigating the effects of inflammation on the body.

InChI:InChI=1/C10H13NO3/c1-14-8-4-2-7(3-5-8)9(11)6-10(12)13/h2-5,9H,6,11H2,1H3,(H,12,13)/t9-/m1/s1

Upstream product

• 135383-36-7 (R)-3-(4-Methoxyphenyl)-N-(R)-α-methylbenzylisoxazolidin-5-one 
• 134781-90-1 (R)-2-tert-Butyl-6-(4-methoxy-phenyl)-tetrahydro-pyrimidin-4-one 
• 171002-20-3 β-(N-phenylacetylamino)-β-(4-methoxyphenyl)propionic acid 
• 6230-11-1 O-Methyltyrosine 
• 873326-22-8 tert-butyl (3R)-3-amino-3-(4-methoxyphenyl)propanoate 
• 951174-19-9 tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-(4'-methoxyphenyl)propanoate 
• 53484-52-9 tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 5678-45-5 3-amino-3-(4-methoxyphenyl)propionic acid 
• 696-62-8 para-iodoanisole 
• 135383-13-0 N-(p-Mthoxybenzylidene)<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 135383-33-4 N-(R)-α-Methylbenzyl-3-(4-methoxyphenyl)isoxazolidin-5-ol 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 131791-83-8 (S)-2-tert-Butyl-6-(4-methoxyphenyl)-5,6-dihydro-4-(1H)-pyrimidinone 

Downstream Products

• 134781-82-1 (R)-β-Tyrosine Methyl Ether Methyl Ester hydrochloride 
• 119717-37-2 jasplakinolide 
• 131791-80-5 N-Boc-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester 
• 134781-91-2 (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 161925-59-3 jaspamide Z₁ 
• 134815-49-9 (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester 
• 511272-33-6 C₂₅H₂₃NO₅ 

Relevant articles and documents

β-styryl- and β-aryl-β-alanine products of phenylalanine aminomutase catalysis

The substrate specificity of a Taxus-derived phenylalanine aminomutase (PAM) was investigated, and the enzyme was found to catalyze the conversion of variously substituted vinyl- and aryl-S-∞-alanines to corresponding β-amino acids. This study shows the b

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis

This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.

Kinetic resolution of aromatic β-amino acids by ω-transaminase

Racemic aromatic β-amino acids have been kinetically resolved into (R)-β-amino acids with high enantiomeric excess (>99%) by a novel ω-TA with ca. 50% conversion.

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids

(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.

Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide

In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a β-amino acid in the cyclopeptide backbone. Their biological profile is also described.

Parallel synthesis of homochiral β-amino acids

The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.

Biocatalytic approach to enatiomerically pure β-amino acids

β-Aryl-β-amino acids were prepared in good chemical yield and high enantiomeric purity (> 95% ee) via penicillin acylase-catalyzed hydrolysis of the corresponding N-phenylacetyl derivatives. The (R)-enantiomers were the fast-reacting isomers in all cases studied. The biocatalytic procedure described employs a very simple set of reactions using inexpensive commercially available chemicals and enzyme, and could be easily scaled up.