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L-Aspartic acid 4-benzyl ester is a crystalline compound derived from L-aspartic acid, an amino acid, and benzyl alcohol. It is characterized by the presence of a benzyl ester group attached to the carboxyl group of the aspartic acid, which gives it unique chemical properties and reactivity.

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  • 2177-63-1 Structure
  • Basic information

    1. Product Name: L-Aspartic acid 4-benzyl ester
    2. Synonyms: H-ASP(OBZL)-OH;H-L-ASP(OBZL)-OH;L-ASPARTIC ACID 4-BENZYL ESTER;L-ASPARTIC ACID BETA-BENZYL ESTER;ASPARTIC ACID(OBZL)-OH;BETA-BENZYL L-ASPARTATE;4-BENZYL L-ASPARTATE;benzyl hydrogen beta-L-aspartate
    3. CAS NO:2177-63-1
    4. Molecular Formula: C11H13NO4
    5. Molecular Weight: 223.23
    6. EINECS: 218-541-8
    7. Product Categories: Amino Acids Derivatives;AMINOACIDS DERIVATIVES;Amino Acids;Aspartic acid [Asp, D];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acid Benzyl Esters;Amino Acids (C-Protected);Biochemistry
    8. Mol File: 2177-63-1.mol
  • Chemical Properties

    1. Melting Point: ~225 °C (dec.)
    2. Boiling Point: 413.1 °C at 760 mmHg
    3. Flash Point: 203.6 °C
    4. Appearance: White/Powder
    5. Density: 1.283 g/cm3
    6. Vapor Pressure: 8.17E-07mmHg at 25°C
    7. Refractive Index: 27 ° (C=1, 1mol/L HCl)
    8. Storage Temp.: −20°C
    9. Solubility: N/A
    10. PKA: 2.16±0.23(Predicted)
    11. Water Solubility: Insoluble in water.
    12. BRN: 1983183
    13. CAS DataBase Reference: L-Aspartic acid 4-benzyl ester(CAS DataBase Reference)
    14. NIST Chemistry Reference: L-Aspartic acid 4-benzyl ester(2177-63-1)
    15. EPA Substance Registry System: L-Aspartic acid 4-benzyl ester(2177-63-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 2177-63-1(Hazardous Substances Data)

2177-63-1 Usage

Uses

Used in Pharmaceutical Industry:
L-Aspartic acid 4-benzyl ester is used as a synthetic intermediate for the development of various pharmaceutical compounds, particularly those with a 1,4-diazepine-2,5-dione ring structure. These compounds have potential applications in the treatment of various medical conditions due to their unique chemical properties and interactions with biological targets.
Used in Polymer Industry:
L-Aspartic acid 4-benzyl ester is also used as a monomer in the development of block copolymers. These copolymers can be utilized in various applications, such as drug delivery systems, where their unique properties can enhance the performance and functionality of the final product. The incorporation of L-aspartic acid 4-benzyl ester into block copolymers can provide specific advantages, such as improved biocompatibility, controlled release of drugs, and enhanced stability.

Check Digit Verification of cas no

The CAS Registry Mumber 2177-63-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,7 and 7 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2177-63:
(6*2)+(5*1)+(4*7)+(3*7)+(2*6)+(1*3)=81
81 % 10 = 1
So 2177-63-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO4/c12-9(6-10(13)14)11(15)16-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,14)/t9-/m0/s1

2177-63-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • TCI America

  • (B3209)  4-Benzyl L-Aspartate  >98.0%(T)

  • 2177-63-1

  • 5g

  • 490.00CNY

  • Detail
  • TCI America

  • (B3209)  4-Benzyl L-Aspartate  >98.0%(T)

  • 2177-63-1

  • 25g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (L08956)  L-Aspartic acid 4-benzyl ester, 98%   

  • 2177-63-1

  • 1g

  • 118.0CNY

  • Detail
  • Alfa Aesar

  • (L08956)  L-Aspartic acid 4-benzyl ester, 98%   

  • 2177-63-1

  • 5g

  • 493.0CNY

  • Detail
  • Alfa Aesar

  • (L08956)  L-Aspartic acid 4-benzyl ester, 98%   

  • 2177-63-1

  • 25g

  • 1653.0CNY

  • Detail
  • Sigma

  • (B2129)  L-Aspartic acid β-benzyl ester  

  • 2177-63-1

  • B2129-25G

  • 2,612.61CNY

  • Detail

2177-63-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-amino-4-oxo-4-phenylmethoxybutanoic acid

1.2 Other means of identification

Product number -
Other names L-Aspartic acid 3-benzyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2177-63-1 SDS

2177-63-1Relevant articles and documents

DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS

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Paragraph 0168; 0169, (2019/04/16)

The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexatnethylenediaanine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 -9 to 10 -5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.

Tumor intelligent targeting and environmental double responsiveness siRNA delivery system and its preparation method and application

-

Paragraph 0039; 0040; 0041; 0042, (2019/02/19)

The invention particularly discloses an intelligent targeting and environmental dual-responsibility siRNA [short interfering RNA (ribonucleic acid)] delivery system for tumor, a preparation method and application. The siRNA delivery system is characterized in that siRNA is concentrated and compounded in nanometer particle nucleuses by the aid of acid-sensitive amphiphilic three-block polymers, and intermolecular disulfide bonds are formed by PAsp(MEA) on sub-surfaces, so that the siRNA can be protected, and the intelligent targeting and environmental dual-responsibility siRNA delivery system can respond to release of the siRNA in reductive cytoplasm. The acid-sensitive amphiphilic three-block polymers comprise polyethylene glycol block-intermediate block-acid-sensitive block three-block copolymers, intermediate blocks comprise polyaspartate acyl mercaptoethylamine, and acid-sensitive blocks comprise poly (diisopropyl amine) ethyl methacrylate. The intelligent targeting and environmental dual-responsibility siRNA delivery system, the preparation method and the application have the advantages that the siRNA delivery system can be applied to preparing intelligent targeting siRNA nanometer medicines for the tumor and is low in N/P ratio dependence degree, and the siRNA can be quickly and completely released at targets; a novel idea can be provided for gene delivery systems, and the intelligent targeting and environmental dual-responsibility siRNA delivery system, the preparation method and the application have important significance on preparing clinical diagnosis and treatment medicines for the tumor.

Photo-thermal chemotherapy and treatment combined microenvironment responsive drug-loading nano micelle preparation method and application

-

Paragraph 0046; 0052-0054, (2019/06/27)

The invention discloses a photo-thermal chemotherapy and treatment combined microenvironment responsive drug-loading nano micelle preparation method and application. A nano micelle comprises TIID-BT,a medicine active component and an amphiphilic block polymer, and the amphiphilic block polymer refers to polyethylene glycol-polyaspartic acid. By synthesis, a near infrared TIID-BT dye and a DOX chemotherapy drug are loaded on the specific nano micelle at the same time to obtain the nano micelle which is capable of giving play to photo-thermal treatment and chemotherapy at the same time. The nano micelle enables DOX to avoid a combination effect of opsonin and a capturing effect of an MPS system to form a stable and long-acting drug delivery system with high drug loading capacity, and accordingly an antitumor effect of DOX is improved while DOX resistance of tumors is changed. In addition, due to loading of the TIID-BT dye in the nano micelle, in-vivo application effects of the TIID-BT dye are improved, combination of hoto-thermal treatment and chemotherapy is realized, and in-vivo tumor treatment effects are improved due to synergistic effects of DOX and TIID-BT.

Preparation method of drug-loaded nano-micelle capable of releasing anti-cancer drug in tumor matrix as well as product and application of drug-loaded nano-micelle

-

Paragraph 0055-0057, (2019/12/25)

The invention relates to a preparation method of a drug-loaded nano-micelle capable of releasing an anti-cancer drug in a tumor matrix as well as a product and an application of the drug-loaded nano-micelle, which belongs to the technical field of drug carriers. The preparation method comprises the following steps: the beta-benzyl aspartate is prepared, benzyloxycarbonyl aspartic anhydride is prepared, a polyaspartic acid benzyl ester polymer is prepared, a carboxylation-polyaspartic acid benzyl ester polymer is prepared, a carboxyl-polyaspartic acid dimethylethylenediamine polymer is prepared, a polyaspartic acid dimethylethylenediamine-polyaspartic acid benzyl ester polymer is prepared, a poly(aspartic acid-dimethylethylenediamine)-poly (aspartic acid-mercaptoethylamine) polymer is prepared, and drug-loaded nano-micelle for releasing an anti-cancer drug in a tumor matrix is prepared. The drug-loaded nano-micelle prepared by the preparation method has double sensitivities of pH sensitivity and reduction sensitivity, can accurately release drugs, and effectively improves the tumor treatment effect.

Thermoresponsive Alignment Media in NMR Spectroscopy: Helix Reversal of a Copolyaspartate at Ambient Temperatures

Schwab, Mira,Schmidts, Volker,Thiele, Christina M.

supporting information, p. 14373 - 14377 (2018/09/20)

Poly(aspartic acid esters) are known to form either right-or left-handed α-helices depending on the ester group in the side chain, on solvent and/or on temperature. Polyphenethyl-l-aspartates (PPLA) exhibit a helix reversal from the right- to the left-handed form with increasing temperature. We have recently reported the application of polyphenethylaspartates as helically chiral alignment media. The thermoresponsivity observed for these polymers offers the possibility to measure different orientations of analytes before and after helix reversal of the alignment medium at 373 K. Herein we present a synthesized copolymer of phenethyl- and benzylaspartate as a new alignment medium undergoing this helix reversal at 303–313 K. Thus, the measurement of residual dipolar couplings (RDC) before and after the helix reversal is allowed for at ambient temperatures. A complete sign change of all 1H–13C RDCs was observed, which is close to the highest possible difference in NMR spectra.

Activity of (+)-Discadenine as a Plant Cytokinin

Mik, Václav,Mi?ková, Zuzana,Dole?al, Karel,Frébort, Ivo,Pospí?il, Tomá?

, p. 2136 - 2140 (2017/08/04)

Discadenine (1), a self-spore germination inhibitor from the cellular slim mold Dictyostelium discoideum, is structurally related to the plant hormone cytokinin. This compound was synthesized from l-aspartic acid, and its activities were confirmed by three classical cytokinin bioassays as well as by using binding and activation assays with the Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4.

Novel preparation method for anti-type-II-diabetes drug sitagliptin

-

Paragraph 0009; 0010; 0011, (2017/09/13)

The invention discloses a novel preparation method for an anti-type-II-diabetes drug sitagliptin. According to the invention, trifluorobenzene with a cheaper price is used as a fluorization reagent and a starting raw material and a basic skeleton of sitagliptin is successfully synthesized through effective acylation of trifluorobenzene and L-aspartic acid; a synthesis route in the invention, from starting raw material and final product, is completely different from schemes disclosed in the prior art; the route is optimized, and easily-available natural L-aspartic acid is used as a chiral source for successful synthesis of an optically pure sitagliptin product; the problems of asymmetric catalysis and complex splitting in the prior art are overcome; the method also effectively overcomes the problem of low yield of the basic skeleton of sitagliptin synthesized via Friedel-Crafts acylation of trifluorobenzene and improves yield; the method is lower in cost, more convenient to operate and more suitable for industrial production; and compared with the prior art, the method is simpler in the synthesis route and better in operability.

A transmission for a total of medicine and liquid fluorocarbon polymer nano vesicle and its preparation method and application

-

Paragraph 0040-0043, (2018/01/11)

The invention relates to an acid-sensitive amphipathic tri-block polymer. The polymer is composed of a polyethylene glycol-acid sensitive segment 1-acid sensitive segment 2 tri-block copolymer, wherein the acid sensitive segment 1 is poly(acrylamidophenylboronic acid); the acid sensitive segment 2 is poly(aminoacyl dimethyl-ethylenediamine); the molecular weight of the polyethylene glycol is 2000-5000, the molecular weight of the acid sensitive segment is 2000-6000, and the molecular weight of the acid sensitive segment is 1000-2000. The invention further relates to application of the acid sensitive amphipathic tri-block polymer in preparation of polymer nano-vesicle for co-delivering drug and perfluorooctylbromide. The nano-vesicle has a uniform nano-diameter, can stably circulate in a body and can be enriched in a tumor position, has excellent capability of reinforcing ultrasonic development to realize application of ultrasonic development under diagnostic ultrasound, and has ultrasonic sensitivity to stimulate the cavitation effect under a condition of low-frequency high-energy ultrasonic-radiation so as to realize controllable release of drugs.

Photo-induced reduction of Cr6+ by the hybrid systems “CuII complex with Schiff base and TiO2”: dependence on irradiation wavelength

Yoshida,Tsaturyan,Akitsu,Tsunoda,Shcherbakov

, p. 2057 - 2065 (2018/03/22)

The synthesis of novel CuII complexes with a Schiff base obtained by condensation of salicylaldehyde and an l-aspartic acid ester are described. The physicochemical properties of the complexes were compared with those of related CuII complexes obtained earlier. All the complexes studied were characterized by elemental analysis as well as by IR, UV-Vis, and EPR spectroscopies. The activity of the complexes and their hybrid systems (HS) with TiO2 in visible-light-driven photocatalysis in organic solvents was investigated. After irradiation with visible light, the complexes and corresponding HS reduce Cr6+ to Cr3+ more efficiently than bare TiO2. To determine the molecular orbital compositions and energies and to explain the electronic spectra and redox properties of the systems studied, density functional calculations of the optimized structures of representative model complexes were performed.

N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis

Milbeo, Pierre,Maurent, Kelly,Moulat, Laure,Lebrun, Aurélien,Didierjean, Claude,Aubert, Emmanuel,Martinez, Jean,Calmès, Monique

, p. 1706 - 1715 (2016/03/08)

A series of N-pyrrolidine-based α,β-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2]octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording β-hydroxy ketones in high yields and good enantioselectivities (up to 87%).

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