Cas no 19887-32-2 (N-Ethoxycarbonyl-L-Phenylalanine)

N-Ethoxycarbonyl-L-Phenylalanine is a protected derivative of L-phenylalanine, where the amino group is shielded by an ethoxycarbonyl (EOC) moiety. This modification enhances stability and prevents unwanted side reactions during peptide synthesis, making it a valuable intermediate in pharmaceutical and biochemical applications. The compound retains the chiral integrity of L-phenylalanine, ensuring compatibility with stereospecific reactions. Its solubility in organic solvents facilitates use in solid-phase and solution-phase peptide coupling methodologies. The EOC group can be selectively removed under mild conditions, offering versatility in multi-step synthetic processes. This derivative is particularly useful in the preparation of complex peptides and modified amino acid analogs.
N-Ethoxycarbonyl-L-Phenylalanine structure
19887-32-2 structure
Product Name:N-Ethoxycarbonyl-L-Phenylalanine
CAS No:19887-32-2
MF:C12H15NO4
MW:237.251803636551
MDL:MFCD00239447
CID:123822
PubChem ID:2817957
Update Time:2025-06-13

N-Ethoxycarbonyl-L-Phenylalanine Chemical and Physical Properties

Names and Identifiers

    • L-Phenylalanine,N-(ethoxycarbonyl)-
    • N-ETHOXYCARBONYL-L-PHENYLALANINE
    • (ethoxycarbonyl)-L-phenylalanine
    • (ethoxycarbonyl)phenylalanine
    • (S)-N-(Ethoxycarbonyl)phenylalanine
    • 2(S)-N-(ethoxycarbonyl)phenylalanine
    • ETOC-PHE-OH
    • N-(ethoxycarbonyl)-L-phenylalanine
    • N-Ethoxycarbonyl-3-phenyl-L-alanine
    • N-ALPHA-ETHOXYCARBONYL-L-PHENYLALANINE
    • (2S)-2-(ethoxycarbonylamino)-3-phenylpropanoic acid
    • (2S)-2-[(ETHOXYCARBONYL)AMINO]-3-PHENYLPROPANOIC ACID
    • AS-30505
    • 19887-32-2
    • L-Phenylalanine, N-(ethoxycarbonyl)-
    • (S)-2-((Ethoxycarbonyl)amino)-3-phenylpropanoicacid
    • EtOCO-Phe
    • MFCD00830554
    • SCHEMBL996291
    • HY-W141826
    • (S)-2-(ethoxycarbonylamino)-3-phenylpropanoic acid
    • CS-0201622
    • AKOS010373673
    • EN300-331410
    • J-012843
    • N-Ethoxycarbonyl-L-phenylalanine (EtOCO-L-Phe-OH)
    • CCG-250428
    • (S)-2-((Ethoxycarbonyl)amino)-3-phenylpropanoic acid
    • MFCD00239447
    • N-Ethoxycarbonyl-L-phenylalanine, 97%
    • YUBBGLSAFZJOMD-JTQLQIEISA-N
    • DA-76114
    • (2S)-2-((ethoxycarbonyl)amino)-3-phenylpropanoic acid
    • 998-140-9
    • UAA88732
    • N-Ethoxycarbonyl-L-Phenylalanine
    • MDL: MFCD00239447
    • Inchi: 1S/C12H15NO4/c1-2-17-12(16)13-10(11(14)15)8-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3,(H,13,16)(H,14,15)/t10-/m0/s1
    • InChI Key: YUBBGLSAFZJOMD-JTQLQIEISA-N
    • SMILES: O(CC)C(N[C@H](C(=O)O)CC1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 237.10000
  • Monoisotopic Mass: 237.10010796g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 7
  • Complexity: 261
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.4
  • Topological Polar Surface Area: 75.6?2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 78-82?°C (lit.)
  • PSA: 75.63000
  • LogP: 1.81930
  • Optical Activity: [α]20/D +25°, c =?2 in ethanol
  • Solubility: Not determined

N-Ethoxycarbonyl-L-Phenylalanine Security Information

  • WGK Germany:3

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N-Ethoxycarbonyl-L-Phenylalanine Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:19887-32-2)N-Ethoxycarbonyl-L-Phenylalanine
Order Number:A1209384
Stock Status:in Stock
Quantity:5g
Purity:99%
Pricing Information Last Updated:Monday, 2 September 2024 15:58
Price ($):173.0

Additional information on N-Ethoxycarbonyl-L-Phenylalanine

Recent Advances in the Application of N-Ethoxycarbonyl-L-Phenylalanine (CAS: 19887-32-2) in Chemical Biology and Pharmaceutical Research

N-Ethoxycarbonyl-L-Phenylalanine (CAS: 19887-32-2) is a protected amino acid derivative that has garnered significant attention in the fields of chemical biology and pharmaceutical research. This compound serves as a crucial building block in peptide synthesis, drug design, and bioconjugation strategies. Recent studies have explored its utility in various applications, ranging from the development of novel therapeutics to the construction of advanced biomaterials. This research brief aims to provide an overview of the latest findings related to this compound, highlighting its potential in advancing scientific and medical innovations.

One of the most notable applications of N-Ethoxycarbonyl-L-Phenylalanine is its role in peptide synthesis. Researchers have utilized this compound as a key intermediate in the solid-phase peptide synthesis (SPPS) of bioactive peptides. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its effectiveness in the synthesis of peptide-based inhibitors targeting proteases involved in cancer progression. The study reported that the ethoxycarbonyl (Eoc) protecting group offered superior stability under acidic conditions compared to other protecting groups, thereby improving the overall yield and purity of the target peptides.

In addition to its applications in peptide synthesis, N-Ethoxycarbonyl-L-Phenylalanine has been investigated for its potential in drug delivery systems. A recent study in Advanced Drug Delivery Reviews (2024) highlighted its use in the design of prodrugs. The researchers found that the Eoc group could be selectively cleaved by esterases in vivo, enabling controlled release of the active drug moiety. This property was leveraged to develop a novel prodrug of an anti-inflammatory agent, which exhibited enhanced bioavailability and reduced side effects in preclinical models.

Another emerging area of research involves the incorporation of N-Ethoxycarbonyl-L-Phenylalanine into biomaterials. A 2024 publication in Biomaterials Science reported the synthesis of a new class of hydrogels functionalized with this compound. The hydrogels demonstrated excellent biocompatibility and were capable of sustained release of growth factors, making them promising candidates for tissue engineering applications. The study also noted that the phenylalanine moiety contributed to the mechanical strength of the hydrogels, further expanding their potential utility.

Beyond its direct applications, N-Ethoxycarbonyl-L-Phenylalanine has also been employed as a chiral auxiliary in asymmetric synthesis. A 2023 study in Organic Letters described its use in the catalytic asymmetric synthesis of β-amino acids, which are important precursors for several pharmaceuticals. The researchers achieved high enantioselectivity and yield, underscoring the versatility of this compound in synthetic chemistry.

In conclusion, N-Ethoxycarbonyl-L-Phenylalanine (CAS: 19887-32-2) continues to be a valuable tool in chemical biology and pharmaceutical research. Its applications span peptide synthesis, drug delivery, biomaterials, and asymmetric synthesis, reflecting its broad utility. Future research is expected to further explore its potential, particularly in the development of next-generation therapeutics and biomaterials. As the field advances, this compound is likely to remain a cornerstone in the toolkit of researchers and industry professionals alike.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:19887-32-2)N-Ethoxycarbonyl-L-Phenylalanine
A1209384
Purity:99%
Quantity:5g
Price ($):173.0
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