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L-Alanine benzyl ester hydrochloride is a white solid benzoxazine derivative with versatile applications in the pharmaceutical and chemical industries. It is known for its role as an additive in the formulation of microemulsions for topical applications and as a reagent in the preparation of collagenase inhibitors.

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  • 5557-83-5 Structure
  • Basic information

    1. Product Name: L-Alanine benzyl ester hydrochloride
    2. Synonyms: ALANINE-OBZL HCL;benzyl L-alaninate hydrochloride;H-Ala-OBzl HCl (L-Alanine benzyl ester.HCl);(S)-Benzyl 2-aMinopropanoate Hydrochloride;L-Alanine PhenylMethyl Ester Hydrochloride;NSC 523831;Alanine benzyl ester (hydrochloride);L-Alanine Benzyl Ester Hydrochloride, 98.0%(LC&T
    3. CAS NO:5557-83-5
    4. Molecular Formula: C10H13NO2*ClH
    5. Molecular Weight: 215.68
    6. EINECS: 226-920-4
    7. Product Categories: Alanine [Ala, A];A - H;Amino Acids;Modified Amino Acids;Amino Acids & Derivatives;Aromatics;Chiral Reagents
    8. Mol File: 5557-83-5.mol
  • Chemical Properties

    1. Melting Point: 140-142°C
    2. Boiling Point: 293 °C at 760 mmHg
    3. Flash Point: 131 °C
    4. Appearance: White to off-white/Powder
    5. Density: 1.1 g/cm3
    6. Vapor Pressure: 0.0154mmHg at 25°C
    7. Refractive Index: 1.53
    8. Storage Temp.: −20°C
    9. Solubility: DMSO, Methanol, Water
    10. CAS DataBase Reference: L-Alanine benzyl ester hydrochloride(CAS DataBase Reference)
    11. NIST Chemistry Reference: L-Alanine benzyl ester hydrochloride(5557-83-5)
    12. EPA Substance Registry System: L-Alanine benzyl ester hydrochloride(5557-83-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5557-83-5(Hazardous Substances Data)

5557-83-5 Usage

Uses

Used in Pharmaceutical Industry:
L-Alanine benzyl ester hydrochloride is used as an additive for the microemulsion formulation of acyclovir, a medication used to treat viral infections. Its role in the formulation enhances the stability and effectiveness of the drug for topical applications.
Used in Chemical Synthesis:
L-Alanine benzyl ester hydrochloride serves as a reagent in the preparation of collagenase inhibitors, which are essential in the development of treatments for various conditions related to the breakdown of collagen, such as arthritis and other connective tissue disorders.
Used in Organic Chemistry:
L-Alanine benzyl ester (ALAB) may be used as an organic reagent in various chemical reactions, contributing to the synthesis of different compounds.
Used in Microemulsions:
L-Alanine benzyl ester hydrochloride is used as a cationic charge inducer in microemulsions, which are mixtures of oil, water, and surfactants. Its presence in these systems improves the stability and performance of the microemulsion, making it suitable for various applications in the pharmaceutical and cosmetic industries.

Check Digit Verification of cas no

The CAS Registry Mumber 5557-83-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,5 and 7 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5557-83:
(6*5)+(5*5)+(4*5)+(3*7)+(2*8)+(1*3)=115
115 % 10 = 5
So 5557-83-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H13NO2/c1-8(11)10(12)13-7-9-5-3-2-4-6-9/h2-6,8H,7,11H2,1H3/t8-/m0/s1

5557-83-5 Well-known Company Product Price

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  • TCI America

  • (A2771)  L-Alanine Benzyl Ester Hydrochloride  >98.0%(HPLC)(T)

  • 5557-83-5

  • 5g

  • 390.00CNY

  • Detail
  • TCI America

  • (A2771)  L-Alanine Benzyl Ester Hydrochloride  >98.0%(HPLC)(T)

  • 5557-83-5

  • 25g

  • 1,560.00CNY

  • Detail

5557-83-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name L-Alanine Benzyl Ester Hydrochloride

1.2 Other means of identification

Product number -
Other names L-Alanine benzyl ester hydrochloride

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:5557-83-5 SDS

5557-83-5Relevant articles and documents

N-transfer reagent and method for preparing the same and its application

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Page/Page column 22-23; 47-50; 51-54, (2021/06/25)

Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.

4'-THIO-NUCLEOTIDE AND -NUCLEOSIDE PRODRUGS FOR THE TREATMENT OF CANCER

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Paragraph 00423, (2019/11/12)

The present disclosure is concerned with 4'-thio nucleotide and nucleoside compounds for the treatment of various cancers such as, for example, sarcomas, carcinomas, hematological cancers, solid tumors, breast cancer, cervical cancer, gastrointestinal cancer, colorectal cancer, brain cancer, skin cancer, prostate cancer, ovarian cancer, bladder cancer, thyroid cancer, testicular cancer, pancreatic cancer, endometrial cancer, melanomas, gliomas, leukemias, lymphomas, chronic myeloproliferative disorders, myelodysplastic syndromes, myeloproliferative neoplasms, and plasma cell neoplasms (myelomas). This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Identification of a 4-fluorobenzyl L-valinate amide benzoxaborole (AN11736) as a potential development candidate for the treatment of Animal African Trypanosomiasis (AAT)

Akama, Tsutomu,Zhang, Yong-Kang,Freund, Yvonne R.,Berry, Pamela,Lee, Joanne,Easom, Eric E.,Jacobs, Robert T.,Plattner, Jacob J.,Witty, Michael J.,Peter, Rosemary,Rowan, Tim G.,Gillingwater, Kirsten,Brun, Reto,Nare, Bakela,Mercer, Luke,Xu, Musheng,Wang, Jiangong,Liang, Hao

, p. 6 - 10 (2017/11/27)

Novel L-valinate amide benzoxaboroles and analogues were designed and synthesized for a structure-activity-relationship (SAR) investigation to optimize the growth inhibitory activity against Trypanosoma congolense (T. congolense) and Trypanosoma vivax (T. vivax) parasites. The study identified 4-fluorobenzyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate (5, AN11736), which showed IC50 values of 0.15 nM against T. congolense and 1.3 nM against T. vivax, and demonstrated 100% efficacy with a single dose of 10 mg/kg against both T. congolense and T. vivax in mouse models of infection (IP dosing) and in the target animal, cattle, dosed intramuscularly. AN11736 has been advanced to early development studies.

Efficient near infrared fluorescence detection of elastase enzyme using peptide-bound unsymmetrical squaraine dye

Saikiran, Maryala,Sato, Daisuke,Pandey, Shyam S.,Hayase, Shuzi,Kato, Tamaki

supporting information, p. 4024 - 4029 (2017/08/23)

Extended wavelength analyte-responsive fluorescent probes are highly desired for the imaging applications owing to their deep tissue penetration, and minimum interference from autofluorescence by biomolecules. Near infra-red (NIR) sensitive and self-quenching fluorescent probe based on the dye-peptide conjugate (SQ 1 PC) was designed and synthesized by facile and efficient one-pot synthetic route for the detection of Elastase activity. In the phosphate buffer solution, there was an efficient quenching of fluorescence of SQ 1 PC (86%) assisted by pronounced dye-dye interaction due to H-aggregate formation. Efficient and fast recovery of this quenched fluorescence of SQ 1 PC (> 50% in 30 s) was observed on hydrolysis of this peptide-dye conjugate by elastase enzyme. Presently designed NIR sensitive self-quenching substrate offers the potential application for the detection of diseases related to proteases by efficient and fast detection of their activities.

Discovery of 2'-α-C-Methyl-2'-β-C-fluorouridine Phosphoramidate Prodrugs as Inhibitors of Hepatitis C Virus

Zeng, Debin,Zhang, Rui,Nie, Quandeng,Cao, Lin,Shang, Luqing,Yin, Zheng

supporting information, p. 1197 - 1201 (2016/12/18)

2′-α-C-Methyl-2′-β-C-fluorouridine and its phosphoramidate prodrugs were synthesized and evaluated for their inhibitory activity against HCV. The structure?activity relationship analysis of the phosphoramidate moiety found that 17m, 17q, and 17r exhibit potent activities against HCV, with EC50 values of 1.82 ± 0.19, 0.88 ± 0.12, and 2.24 ± 0.22 μM, respectively. The docking study revealed that the recognition of the 2′-β-F by Arg158, 3′-OH by N291, and the Watson?Crick pairing with the template allowed 23 to form the in-line conformation necessary for its incorporation into the viral RNA chain.

4'-Difluoromethyl Substituted Nucleoside Derivatives as Inhibitors of Influenza RNA Replication

-

, (2015/09/22)

The application discloses nucleoside derivatives of Formula I as inhibitors of Influenza RNA replication. In particular, the application discloses the use of purine and pyrimidine nucleoside derivatives of Formula I as inhibitors of Influenza RNA replication and pharmaceutical compositions containing such compounds.

Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms

Ulatowski, Filip,Jurczak, Janusz

, p. 4235 - 4243 (2015/05/13)

Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

Novel Isobaric Tandem Mass Tags for Quantitative Proteomics and Peptidomics

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Paragraph 0199, (2013/04/10)

Compositions and methods of tagging peptides and other molecules using novel isobaric tandem mass tagging reagents, including novel N,N-dimethylated amino acid 8-plex and 16-plex isobaric tandem mass tagging reagents. The tagging reagents comprise: a) a reporter group having at least one atom that is optionally isotopically labeled; b) a balancing group, also having at least one atom that is optionally isotopically labeled, and c) an amine reactive group. The tagging reagents disclosed herein serve as attractive alternatives for isobaric tag for relative and absolute quantitation (iTRAQ) and tandem mass tags (TMTs) due to their synthetic simplicity, labeling efficiency and improved fragmentation efficiency.

A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis

Wu, Jianhui,Li, Chunyu,Zhao, Ming,Wang, Wenjing,Wang, Yuji,Peng, Shiqi

experimental part, p. 6220 - 6229 (2010/10/04)

Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC 50 values against five human carcinoma cell lines ranged from 11.1 μM to more than 100 μM. The in vivo assay identified five derivatives of them had no anti-tumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue.

Esterification of unprotected a-Amino acids in ionic liquids as the reaction media

Biondini, Daniele,Brinchi, Lucia,Germani, Raimondo,Goracci, Laura,Savelli, Gianfranco

experimental part, p. 39 - 44 (2010/08/22)

Ionic liquid 1,3-dimethylimidazolium methanesulfonate was used to prepare a-amino acids benzylic esters from unprotected amino acids and benzyl chloride. Esterification of several amino acids was achieved with satisfactory yields: by-products can be removed by a simple work-up procedure to afford the pure product. The described method is simple, mild, rapid and save.

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