Methyl hippurate

Base Information

• Chemical Name: Methyl hippurate
• CAS No.: 1205-08-9
• Molecular Formula: C10H11 N O3
• Molecular Weight: 193.202
• Hs Code.: 2924299090
• European Community (EC) Number: 622-893-1
• DSSTox Substance ID: DTXSID90152880
• Nikkaji Number: J103.970I
• Wikidata: Q27139159
• Metabolomics Workbench ID: 37469
• ChEMBL ID: CHEMBL218718
• Mol file: 1205-08-9.mol

Synonyms:methyl 2-benzamidoacetate;Methyl hippurate;1205-08-9;Methyl N-benzoylglycinate;BENZOYLGLYCINE METHYL ESTER;Hippuric acid, methyl ester;Methyl (benzoylamino)acetate;Glycine, N-benzoyl-, methyl ester;N-Benzoylglycine methyl ester;methyl 2-(phenylformamido)acetate;Hippuric acid methyl ester;Hippurate methyl ester;N-benzoyl-Glycine methyl ester;CHEBI:70869;MFCD00025882;methylhippurate;Methylhippurat;Methyl benzoylglycinate;Enamine_005885;Methyl benzoylaminoacetate;benzoylglycin methyl ester;MLS001049059;Methyl ester of Hippuric acid;methyl 2-(benzoylamino)acetate;CCG-17;CHEMBL218718;SCHEMBL3961994;DTXSID90152880;HMS1410L11;HMS2270H24;methyl N-(phenylcarbonyl)glycinate;AMY10566;STK708263;AKOS000659809;IDI1_008120;NCGC00246304-01;AS-59164;SMR000386897;SY033495;CS-0150655;FT-0633483;L10157;AB00698021-06;A892176;SR-01000391982;SR-01000391982-1;SR-01000391982-2;Q27139159;4639-10-5

Chemical Property of Methyl hippurate

Chemical Property:

• Vapor Pressure: 4.74E-06mmHg at 25°C
• Melting Point: 82-83℃
• Boiling Point: 382.4°Cat760mmHg
• Flash Point: 185.1°C
• PSA: 58.89000
• Density: 1.161g/cm³
• LogP: 1.16420
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-benzamidoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CNC(=O)C1=CC=CC=C1
• Uses: Methyl 2-Benzamidoacetate can be used to prepare heteroaromatic inhibitors of astacin proteinases.

Technology Process of Methyl hippurate

There total 90 articles about Methyl hippurate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + benzoyl chloride (98-88-4) → methyl hippurate (1205-08-9)

Guidance literature:

With triethylamine; In chloroform; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00479-1

Reference yield: 99.0%

Hippuric Acid (495-69-2,140480-84-8,21251-67-2,91787-63-2,66407-11-2) + methanol (67-56-1) → methyl hippurate (1205-08-9)

Guidance literature:

With tetrachloromethane; at 20 ℃; for 2.5h; UV-irradiation;

DOI:10.1016/j.tetlet.2004.04.155

Reference yield: 98.0%

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + benzoic acid (65-85-0,8013-63-6) → methyl hippurate (1205-08-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.chembiol.2019.02.009

upstream raw materials:

diazomethane

Hippuric Acid

methanol

hippuroylmercapto-acetic acid

Downstream raw materials:

N-2-(2-hydroxyethylamino)-2-oxoethylbenzamide

hippuroyl-guanidine

methyl N-benzoyl-2-methoxyglycinate

α,α-dimethoxy-N-benzoyl-glycine methyl ester

Refernces

• 1、 Bernhard et al.. "". . p. 3043,3044-3050. Retrieved 1960.
• 2、 Mazurkiewicz, Roman,Pierwocha, Anna W.,Zabska, Agata. "Hydro-de-phosphoniation of 4-substituted-4-triphenylphosphonio-5(4H)-oxazolones with hydrogen iodide". . p. 167 - 178. Retrieved 1999.
• 3、 Rinderknecht,Niemann. "-". . p. 2605. Retrieved 1948.
• 4、 Kaminski, Zbigniew J.. "2-CHLORO-4,6-DISUBSTITUTED-1,3,5,-TRIAZINES A NOVEL GROUP OF CONDENSING REAGENTS". . p. 2901 - 2904. Retrieved 1985.
• 5、 Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao. "Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite". supporting information. p. 2713 - 2718. Retrieved 2021/06/25.