72784-43-1

Basic information

• Product Name: Methyl 1-Aminocyclopropanecarboxylate
• Synonyms: Methyl 1-Aminocyclopropanecarboxylate;Methyl 1-aminocyclopropane-1-carboxylate;ACPCM;Methyl 1-amino-1-cyclopropylcarboxylate;Cyclopropanecarboxylic acid, 1-aMino-, Methyl ester
• CAS NO: 72784-43-1
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• Product Categories: Amino Acids and Derivatives
• Mol File: 72784-43-1.mol

Chemical Properties

• Boiling Point: 136℃
• Flash Point: 12℃
• Appearance: /
• Density: 1.188
• Vapor Pressure: 7.4mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 6.01±0.20(Predicted)
• CAS DataBase Reference: Methyl 1-Aminocyclopropanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-Aminocyclopropanecarboxylate(72784-43-1)
• EPA Substance Registry System: Methyl 1-Aminocyclopropanecarboxylate(72784-43-1)

Safety Data

• Hazardous Substances Data: 72784-43-1(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
Methyl 1-aminocyclopropanecarboxylate is used as a research tool for studying the regulation of ethylene biosynthesis, a hormone that plays a crucial role in plant growth and development. It helps researchers understand the physiological and biochemical processes related to plant growth and stress responses.
Used in Agricultural Applications:
In the agricultural industry, Methyl 1-aminocyclopropanecarboxylate is used as a precursor for the synthesis of ACC, which is involved in the regulation of ethylene biosynthesis. This helps in improving crop yield, quality, and resistance to various stress factors such as drought, salinity, and disease. By modulating the levels of ACC, it can potentially enhance plant growth and development, leading to better agricultural outcomes.

InChI:InChI=1/C5H9NO2/c1-8-4(7)5(6)2-3-5/h2-3,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 22059-21-8 aminocyclopropane-1-carboxylic acid 
• 72784-42-0 methyl 1-aminocyclopropane-1-carboxylate hydrochloride 
• 145618-70-8 1-(Benzhydrylidene-amino)-cyclopropanecarboxylic acid methyl ester 
• 914223-82-8 (9H-fluoren-9-yl)methyl 1-(methoxycarbonyl)-cyclopropylcarbamate 

Downstream Products

• 2483-62-7 methyl 2-aminobutanoate 
• 547-63-7 Methyl isobutyrate 
• 13257-67-5 2-amino-2-methylpropionic acid methyl ester 
• 74-85-1 ethene 
• 109-78-4 3-Hydroxypropionitrile 
• 191033-52-0 1-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-cyclopropanecarboxylic acid methyl ester 
• 191033-48-4 N-Cbz-(S)-phenylalanine-(S)-cyclopropanecarboxylic acid methyl ester 
• 191033-44-0 1-(2-Benzyloxycarbonylamino-acetylamino)-cyclopropanecarboxylic acid methyl ester 
• 868623-74-9 1-[4-(2-nitrobenzenesulfonyl)-piperazin-1-yl]-cyclopropanecarboxylic acid methyl ester 
• 1071157-71-5 1-{5-[3-(Cyclohexyl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-cyclopropanecarboxylic acid methyl ester 
• 1034926-21-0 C₁₂H₁₁BrF₃NO₄S 
• 1260155-60-9 C₂₁H₂₄N₄O₃ 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF DISEASE

Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-{4-[3-methyl-4((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-{5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups

Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in

Synthesis and biological evaluation of 12 allenic aromatic ethers

Twelve allenic aromatic ethers, some of them are natural products isolated from the mangrove fungus Xylaria sp. 2508 in the South China Sea, were synthesized. Their antitumor activities against KB and KBv200 cells were determined. All these compounds demonstrated cytotoxic potential, ranging from weak to strong activity. The analysis of structure-activity relationships suggested that the introduction of allenic moiety could generate or enhance cytotoxicity of these phenol compounds.

Potential anti-inflammatory actions of the elmiric (lipoamino) acids

A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the J series predominates over the E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.

Partial agonists of the strychnine insensitive glycine modulatory site of the N-methyl-D-aspartate receptor complex as neuropsychopharmacological agents

A method is disclosed for the treatment of neuropsychopharmacological disorders which are associated with or result from excessive activation of the N-methyl-D-aspartate receptor complex, which method comprises administering an effective neuropsychopharmacological disorder-treating amount of a compound possessing partial agonist properties for the strychnine insensitive glycine modulatory sites of N-methyl-D-aspartate receptors. Exemplary of partial agonists which are useful in the method of the invention are 1-aminocyclopropanecarboxylic acid, and associated derivates thereof. Novel injectable pharmaceutical compositions are also disclosed.

β-turn preferences induced by 2,3-methanophenylalanine chirality

The model dipeptides RCO-L-Pro-c3-Phe-NHMe, where c3Phe stands for each of the four cyclopropane analogues of phenylalanine (2,3- methanophenylalanine), have been studied in solution by using 1H NMR and FT- IR spectroscopy and in the solid state by using X-ray diffraction. The conformational behavior of these compounds has been compared to that of the analogous Ac3c and L- or D-Phe-containing dipeptides. When associated to proline, the cyclopropane residues in the so-called i + 2 position exhibit a marked tendency to β-folding in solution, even in DMSO. The type II β-turn is generally favored, but the βI/βII-turn ratio depends both on the experimental conditions (solvent, solution, or solid state) and on the chirality of the c3Phe moeity, which rigidly fixes the orientation of the phenyl ring with respect to the peptide backbone. The (2S,3S)c3Phe residue, analogous to L-Phe with the χ1 angle constrained to about 0°, is the most propitious to βI-folding in the i + 2 position of a putative β-turn.

Treatment of mood disorders with functional antagonists of the glycine/NMDA receptor complex

A method is disclosed for the treatment of mood disorders, including major depression, by administering an effective mood disorder treating amount of a compound possessing functional antagonist properties for the N-methyl-D-aspartate receptor complex.

Decarboxylation of 1-Aminocyclopropanecarboxylic Acid and Its Derivatives

The question of whether the title compounds could be decarboxylated to cyclopropanone derivatives was answered in the affirmative by the following observations. (1) Compound 11a was decarboxylated by 1,2,3-indantrione in acetonitrile, benzene, or methanol.The initially formed intermediate could be trapped by N-phenylmaleimide (to form 3), by diethyl azodicarboxylate (to form an unstable adduct), by ninhydrin itself (to form 5) or by a proton (in methanol, to form 8). (2) Compound 11d was decarboxylated by phenylbis(trifluoroacetato-O)iodine to yield carbinolamine 12d.cis-2,3-Dideuterio-11d yielded cis-2,3-dideuterio-12d under the same conditions. (3) ACC was decarboxylated by phenanthroquinone to yield oxazole 9, probably by way of oxazoline 10.

Regioselectivity in the Catalytic Hydrogenolysis of 1-Amino-1-cyclopropanecarboxylic Acid and Its Methyl Ester

The title compounds were hydrogenolyzed over Pd-C.The ring-bond cleavage in the hydrogenolysis of the acid in water or methanol occurred at both the C1-C2 bond and the C2-C3 bond in nearly equal proportion, whereas the C1-C2 bond was cleaved mainly in the presence of ammonia and the C2-C3 bond was cleaved mainly in acetic acid.Selective hydrogenolysis of the C1-C2 bond of ester occurred in hexane or methanol, whereas the C2-C3 bond was hydrogenolyzed mainly in acetic acid.The role of the amino group is discussed.