4430-97-1

Basic information

• Product Name: 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid
• Synonyms: 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid;Dopaquinone
• CAS NO: 4430-97-1
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.17
• Mol File: 4430-97-1.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 419.5°Cat760mmHg
• Flash Point: 207.5°C
• Appearance: /
• Density: 1.426g/cm³
• Vapor Pressure: 3.25E-08mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid(4430-97-1)
• EPA Substance Registry System: 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid(4430-97-1)

Safety Data

• Hazardous Substances Data: 4430-97-1(Hazardous Substances Data)

Usage

General Description

2-Amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid, also known as 2-amino-6-oxocyclohex-3-ene-1-carboxylic acid, is a chemical compound with a complex structure. It possesses an amino group, a carboxylic acid group, and a unique cyclohexadienyl moiety. 2-amino-3-(3,4-dioxo-1-cyclohexa-1,5-dienyl)-propanoic acid is a derivative of cyclohexa-1,5-dienylpropanoic acid and has potential applications in organic and pharmaceutical chemistry. It may be used as a building block for the synthesis of other compounds with diverse properties and functions. Its structural and functional versatility make it an interesting target for further research and exploration in the field of chemical and medicinal science.

InChI:InChI=1/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)

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Relevant articles and documents

CHROMATOGRAPHIC AND SPECTROSCOPIC INVESTIGATION OF THE PRODUCTS OF OXIDATION OF TYROSINE WITH OZONE.

It has been shown that ozone in low concentrations readily oxidizes aromatic amino acids both in solution and when constituents of proteins resulting in the formation of a whole series of oxidation products. Since the oxidation products are physiologically active it was of interest to study them further. In the present work the main molecular products obtained by oxidation of tyrosine with ozone are established, and possible mechanisms of their formation discussed.

Biochemical characterization of two differentially expressed polyphenol oxidases from hybrid poplar

Two polyphenol oxidase isoforms with distinct expression patterns were identified in hybrid poplar (Populus trichocarpax P. deltoides). PPO-1, corresponding to the previously cloned PtdPPO (Constabel et al., Plant Physiol. 124: 285-295) was primarily leaf

Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches

p-Coumaric acid is a known inhibitor of tyrosinase, an enzyme involved in the initial steps of the melanin synthesis in human and other species. However, its low lipophilicity impairs its penetration through skin and efficacy as antimelanogenic agent indeed. Accordingly, this paper reports the assessment of several coumaric acid derivatives as tyrosinase inhibitors and antimelanogenic agents in in vitro, in silico and ex vivo assays. The compounds were designed with modifications in the aromatic and acid moieties of p-coumaric acid, being the coumarate esters the most promising derivatives. The compounds showed higher tyrosinase inhibitory activity (pIC50 3.7–4.2) than the parent acid, being compounds 1d, 1e and 1f the most potent inhibitors. Docking analysis showed that these esters are competitive inhibitors per se, and act independently of a redox mechanism as suggested by DPPH assays. Moreover, the esters showed efficacy in reducing the melanin deposition in human skin fragments at 0.1% concentration, especially compound 1e. In summary, there is an important equilibria between tyrosinase affinity and lipophilicity that must be considered to get effective antimelanogenic agents with adequate permeability in the skin.

Inhibitory effects and molecular mechanism on mushroom tyrosinase by condensed tannins isolation from the fruit of Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chow

The structure of extracted condensed tannin (CT) from the fruit of Sour jujube (Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chow) and the molecular mechanisms by which CT inhibits the activity of mushroom tyrosinase were investigated. The structure of CT was characterized by high performance liquid chromatography electrospray ionization mass spectrometry, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The kinetic assays were used to detect inhibition effect, type and mechanism. UV scanning, fluorescence quenching, copper interacting, o-quinone interaction and molecular docking assays were also used to reveal the molecular mechanisms by which CT inhibit tyrosinase. The results showed the structural units of CT containing afzelechin/epiafzelechin, catechin/epicatechin, and gallocatechin/epigallocatechin. Kinetic analysis showed that CT inhibits both the monophenolase and diphenolase activities of tyrosinase and exhibits reversible, mixed type mechanism. The fruit CT interacts primarily with the copper ions and specific amino acid residue (Asn191, Thr203, Ala202, Ser206, Met201, His194, His54, Glu182 and Ile42) in the active site of tyrosinase to disturb oxidation of substrates by tyrosinase. These results suggested the sour jujube fruit is a potential natural source of tyrosinase inhibitors, and has a potential to be used in food preservation, whitening cosmetics.