6384-18-5

Basic information

• Product Name: dimethyl L-aspartate
• Synonyms: dimethyl L-aspartate;3-(Methoxycarbonyl)-L-alanine methyl ester;Dimethyl aspartate;L-Aspartic acid 1,4-dimethyl ester
• CAS NO: 6384-18-5
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.15584
• EINECS: 228-982-8
• Mol File: 6384-18-5.mol
• Article Data: 55

Chemical Properties

• Melting Point: 115-116 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• Boiling Point: 119-120 °C(Press: 16 Torr)
• Appearance: /
• Density: 1.162±0.06 g/cm3(Predicted)
• PKA: 5.90±0.33(Predicted)
• CAS DataBase Reference: dimethyl L-aspartate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl L-aspartate(6384-18-5)
• EPA Substance Registry System: dimethyl L-aspartate(6384-18-5)

Safety Data

• Hazardous Substances Data: 6384-18-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H11NO4/c1-10-5(8)3-4(7)6(9)11-2/h4H,3,7H2,1-2H3/t4-/m0/s1

Upstream product

• 67-56-1 methanol 
• 56-84-8 L-Aspartic acid 
• 17585-59-0 L-aspartic acid hydrochloride 
• 32213-95-9 dimethyl L-aspartate hydrochloride 
• 149-73-5 trimethyl orthoformate 
• 13726-67-5 Boc-Asp-OH 
• 699020-10-5 dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate 
• 35909-93-4 dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 70-47-3 L-asparagine 
• 1202654-84-9 C₁₀H₁₉NO₆S 
• 2177-62-0 β-methyl L-aspartate 
• 1356449-87-0 calyxamide A 
• 1356449-88-1 calyxamide B 
• 142026-01-5 (R)-dimethyl 2-azidosuccinate 

Downstream Products

• 102324-41-4 N-[N²-benzyloxycarbonyl-N⁶-(toluene-4-sulfonyl)-L-lysyl]-L-aspartic acid dimethyl ester 
• 81083-58-1 diethyl N-(2,2,2-trifluoroacetyl)-L-aspartate 
• 6437-34-9 (3,6-dioxo-piperazine-2,5-diyl)-bis-acetic acid dimethyl ester 
• 6560-37-8 2,2'-(3,6-dioxopiperazine-2,5-diyl)diacetic acid 
• 4685-12-5 glycyl-L-aspartic acid 
• 3588-70-3 N-(4-phenylazo-benzoyl)-L-aspartic acid dimethyl ester 
• 2177-62-0 β-methyl L-aspartate 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 120418-37-3 CBZAlaAsp(OCH₃)2 
• 115446-33-8 (S)-2-((S)-6-Benzyloxycarbonylamino-2-butyrylamino-hexanoylamino)-succinic acid dimethyl ester 
• 115446-34-9 (S)-2-((S)-6-Benzyloxycarbonylamino-2-octanoylamino-hexanoylamino)-succinic acid dimethyl ester 
• 115446-35-0 (S)-2-((S)-6-Benzyloxycarbonylamino-2-hexadecanoylamino-hexanoylamino)-succinic acid dimethyl ester 
• 142026-06-0 Cbz-Ala-D-Asp(OMe)-OMe 
• 65414-78-0 (R)-Aspartate α-methyl ester 

Relevant articles and documents

Oxovanadium(IV) complexes of salicyl-L-aspartic acid and salicylglycyl-L-aspartic acid

The dipeptide and tripeptide analogues salicyl-L-aspartic acid (Sal-L-Asp) and salicylglycyl-L-aspartic acid (SalGly-L-Asp) were synthesized and their protonation and complex formation with VIVO2+ were studied in aqueous solution through the use of pH-potentiometry and spectroscopic (UV-Vis, CD and EPR) techniques. The phenolate terminus proved to be a good anchoring site to promote (i) the metal ion-induced deprotonation and subsequent coordination of the peptide amide group(s) in the pH range 4-5 for the dipeptide analogue, (ii) and in the pH range 5-6 in a very cooperative way for the tripeptide analogue. The results suggest that the presence of good anchoring donors on both sides of the amide groups is responsible for the cooperative deprotonation of the two amide-NH groups. The Royal Society of Chemistry 2005.

Reaction of aspartic acid derivatives with Grignard reagents - Synthesis of γ,γ-disubstituted α- and β-amino-butyrolactones

A series of γ,γ-dimethyl and γ,γ-diphenyl substituted α- and β-amino-butyrolactones have been prepared in enantiomerically pure form using L-aspartic acid as a chiral building block. For the final Grignard reaction the difference in chemical reactivity between the carboxyl groups of aspartic acid was increased or inverted by preparing the corresponding semiesters, diesters and anhydrides. The resulting hydroxyacids and hydroxyesters lactonised in most cases during work up. Thus, (2S)-2-ethoxycarbonylamino-succinic acid-4-methylester 1 reacted with methylmagnesium iodide to form (3S)-3-ethoxycarbonylamino-5,5-dimethyl-tetrahydrofuran-2-one 2b. Two interesting side products were obtained and were found to result from attack at the C-1 carboxylic acid rather than the C-4 carboxylic ester group leading to (3S)-3-ethoxycarbonylamino-4-oxo-pentanoic acid methylester 3 and (4S)-4-ethoxycarbonylamino-5,5-dimethyl-tetrahydrofuran-2-one 5a. Copyright (C) 2000 Elsevier Science Ltd.

A Biocompatible Aspartic-Decorated Metal-Organic Framework with Tubular Motif Degradable under Physiological Conditions

Achieving a precise control of the final structure of metal-organic frameworks (MOFs) is necessary to obtain desired physical properties. Here, we describe how the use of a metalloligand design strategy and a judicious choice of ligands inspired from nature is a versatile approach to succeed in this challenging task. We report a new porous chiral MOF, with the formula Ca5II{CuII10[(S,S)-aspartamox]5}·160H2O (1), constructed from Cu2+and Ca2+ions and aspartic acid-decorated ligands, where biometal Cu2+ions are bridged by the carboxylate groups of aspartic acid moieties. The structure of MOF1reveals an infinite network of basket-like cages, built by 10 crystallographically distinct Cu(II) metal ions and five aspartamox ligands acting as bricks of a tubular motif, composed of seven basket-like cages each. The pillared hepta-packed cages generate pseudo-rhombohedral nanosized channels of ca. 0.7 and 0.4 nm along thebandacrystallographic axes. This intricate porous 3D network is anionic and chiral, each cage displaying receptor properties toward three-nuclear [Ca3(μ-H2O)4(H2O)17]6+entities. represents the first example of an extended porous structure based on essential biometals Cu2+and Ca2+ions together with aspartic acid as amino acid. shows good biocompatibility, making it a good candidate to be used as a drug carrier, and hydrolyzes in acid water. The hypothesis has been further supported by an adsorption experiment here reported, as a proof-of-principle study, using dopamine hydrochloride as a model drug to follow the encapsulation process. Results validate the potential ability of to act as a drug carrier. Thus, these make this MOF one of the few examples of biocompatible and degradable porous solid carriers for eventual release of drugs in the stomach stimulated by gastric low pH.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.