267650-37-3

Basic information

• Product Name: L-Styrylalanine
• Synonyms: L-STYRYLALANINE;H-ALA(STYR)-OH;H-ALA(STYRYL)-OH;3-STYRYL-L-ALANINE;RARECHEM BK PT 0177;(E,2S)-2-Amino-5-phenylpent-4-enoic acid;L-Styryl-Ala-OH;L-Strylalanine
• CAS NO: 267650-37-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 267650-37-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 399.4 °C at 760 mmHg
• Flash Point: 195.4 °C
• Appearance: /
• Density: 1.179 g/cm³
• Vapor Pressure: 4.26E-07mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: Store at -15°C
• PKA: 2.25±0.10(Predicted)
• CAS DataBase Reference: L-Styrylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Styrylalanine(267650-37-3)
• EPA Substance Registry System: L-Styrylalanine(267650-37-3)

Safety Data

• Hazardous Substances Data: 267650-37-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C11H13NO2/c12-10(11(13)14)8-4-7-9-5-2-1-3-6-9/h1-7,10H,8,12H2,(H,13,14)/b7-4+/t10-/m0/s1

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 108246-15-7 (+/-)-4-Acetamino-1-phenyl-penten-⁽¹⁾-saeure-⁽⁵⁾ 
• 101782-54-1 Acetamino-cinnamyl-malonsaeure-diethylester 
• 60691-90-9 3-bromo-1-(p-chlorophenyl)-1-propene 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 121786-28-5 rac-(E)-2-amino-5-phenylpent-4-enoic acid 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 121704-11-8 (E)-2-(2-Methoxy-acetylamino)-5-phenyl-pent-4-enoic acid 
• 109838-85-9 (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 101585-55-1 formylamino-(3-phenyl-prop-2-ynyl)-malonic acid diethyl ester 
• 101583-20-4 cis-cinnamyl-formylamino-malonic acid diethyl ester 
• 4746-62-7 2-amino-2-hydroxyacetic acid 

Downstream Products

• 121786-28-5 rac-(E)-2-amino-5-phenylpent-4-enoic acid 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 52161-76-9 (E,2S)-2-amino-5-phenyl-pent-4-enoic acid 
• 919529-76-3 (R,E)-2-((tert-butoxycarbonyl)amino)-5-phenylpent-4-enoic acid 

Relevant articles and documents

Synthesis of Optically Pure (S, E)-2-Amino-5-arylpent-4-enoic Acids by Heck Reactions of Nickel Complexes

Starting from commercially available building blocks a variety of enantiomerically pure (S)-2-amino-4-enoic acids has been synthesized by the Heck reaction using Ni-(S)-BPB {Nickel- N -[(S)-benzylprolyl]aminobenzophenone} as a chiral auxiliary. The reactions proceeded in very good yields and with high E -selectivity.

Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky l- and d-Arylalanines

Tailored mutants of phenylalanine ammonia-lyase from Petroselinum crispum (PcPAL) were created and tested in ammonia elimination from various sterically demanding, non-natural analogues of phenylalanine and in ammonia addition reactions into the corresponding (E)-arylacrylates. The wild-type PcPAL was inert or exhibited quite poor conversions in both reactions with all members of the substrate panel. Appropriate single mutations of residue F137 and the highly conserved residue I460 resulted in PcPAL variants that were active in ammonia elimination but still had a poor activity in ammonia addition onto bulky substrates. However, combined mutations that involve I460 besides the well-studied F137 led to mutants that exhibited activity in ammonia addition as well. The synergistic multiple mutations resulted in substantial substrate scope extension of PcPAL and opened up new biocatalytic routes for the synthesis of both enantiomers of valuable phenylalanine analogues, such as (4-methoxyphenyl)-, (napthalen-2-yl)-, ([1,1′-biphenyl]-4-yl)-, (4′-fluoro-[1,1′-biphenyl]-4-yl)-, and (5-phenylthiophene-2-yl)alanines.

Microwave-assisted synthesis of unnatural amino acids

Microwave irradiation has been proven to be a useful tool in the rapid assembly of racemic unnatural amino acids in only two steps. Additional benefits of this methodology are the commercial availability of the inexpensive starting materials and the high yields and high purities of the final amino acid products.