188674-57-9

Basic information

• Product Name: 2,3-Pentanedione, 4,5-dihydroxy-, (R)- (9CI)
• Synonyms: 2,3-Pentanedione, 4,5-dihydroxy-, (R)- (9CI)
• CAS NO: 188674-57-9
• Molecular Formula: C5H8O4
• Molecular Weight: 132.11462
• Product Categories: ACETYLGROUP
• Mol File: 188674-57-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 263.0±30.0 °C(Predicted)
• Appearance: /
• Density: 1.311±0.06 g/cm3(Predicted)
• PKA: 11.36±0.20(Predicted)
• CAS DataBase Reference: 2,3-Pentanedione, 4,5-dihydroxy-, (R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Pentanedione, 4,5-dihydroxy-, (R)- (9CI)(188674-57-9)
• EPA Substance Registry System: 2,3-Pentanedione, 4,5-dihydroxy-, (R)- (9CI)(188674-57-9)

Safety Data

• Hazardous Substances Data: 188674-57-9(Hazardous Substances Data)

Usage

Description

2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is an organic compound with the molecular formula C5H8O3. It is a chiral molecule, with the (R)-enantiomer being one of its two possible stereoisomers. 2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Synthesis:
2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is used as a synthetic building block for the development of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules with different properties and applications.
Used in Bioluminescence Research:
2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is used as a precursor in the synthesis of auto-inducers, which are signaling molecules involved in the regulation of bioluminescence in certain organisms. This application is particularly relevant in the field of biotechnology, where understanding and controlling bioluminescence can have significant implications for the development of new technologies and applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the compound's unique structure and chirality may make it a potential candidate for the development of new drugs or drug delivery systems. Further research and development in this area could lead to the discovery of novel therapeutic agents.

Upstream product

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• 643-71-0 D-glucosone 
• 1228078-27-0 (4R)-1-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-propane-1,2-dione 
• 848035-10-9 (S)-1,2-cyclohexylidenedioxypent-3-yne 
• 880872-28-6 1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-1,1-dihydroxy-propan-2-one 
• 848035-08-5 (R)-4,5-cyclohexylidenedioxy-2,3-pentanedione 
• 848035-00-7 (R)-1,2-cyclohexylidenedioxypent-3-yne 
• 1278444-56-6 (R)-1-(tert-butyldiphenylsilyloxy)pent-3-yn-2-ol 
• 710324-25-7 (R)-2,2-Dimethyl-4-prop-1-ynyl-[1,3]dioxolane 
• 500596-40-7 (R)-pent-3-yne-1,2-diol 

Relevant articles and documents

Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi

Bacteria can coordinate community-wide behaviors through quorum sensing, that is, the secretion and sensing of autoinducer (AI) molecules. Bacterial quorum sensing is implicated in the regulation of pathologically relevant events such as biofilm formation, bacterial virulence, and drug resistance. Inhibitors of bacterial quorum sensing could therefore be useful therapeutics. Herein we report for the first time the discovery of several pyrogallol compounds as single digit micromolar inhibitors of bacterial quorum sensing in Vibrio harveyi.

Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs

Autoinducer-2 (AI-2) has been suggested to serve as a universal interspecies quorum sensing signaling molecule. We have synthesized a set of AI-2 analogs with small incremental changes in alkyl substitution on C-2 and evaluated them for their agonistic and antagonistic potential as quorum sensing (QS) attenuators in two different bacterial species: Pseudomonas aeruginosa and Vibrio harveyi. Unexpectedly, several of the analogs were found to function as synergistic QS agonists in V. harveyi, while two of these analogs inhibit QS in P. aeruginosa.

Synthesis and biological validation of a ubiquitous quorum-sensing molecule

Chemical communication ("quorum sensing") amongst bacteria has been studied by the synthesis and study of enantiopure (R)-4,5-dihydroxy-2,3- pentanedione (DPD, see scheme). Bioactivity assays with DPD have shown that chelation of boron by the cyclic form of DPD appears to be essential for full induction of bioluminescence, which is an example of quorum-sensing-controlled behavior.

5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to ellman's reagent

(Chemical Equation Presented) 5-(2-Aminoethyl)dithio-2-nitrobenzoate (ADNB) reacts with free thiols with kinetics similar to those of Ellman's reagent but has dramatically improved stability under alkaline conditions, making it an excellent alternative to Ellman's reagent for the quantitation of thiol contents and enzymatic assays under basic pH conditions.

Maillard Browning Inhibition by Ellagic Acid via Its Adduct Formation with the Amadori Rearrangement Product

The Maillard reaction performed under a stepwise increase of temperature was applied for researching the inhibition of Maillard browning caused by ellagic acid. Ellagic acid was found effective for the inhibition of melanoidin formation in the xylose-glycine Maillard reaction but depended on its dosage and the point of time it was added in the reaction system. The lightest color of the Maillard reaction products was observed when ellagic acid was added at the 90th min, which was the point of time when the Amadori rearrangement product (ARP) developed the most. LC-ESI-MS/MS analysis results showed a significant tendency of the ellagic acid hydrolysis product to react with the predominant intermediate ARP to yield an adduct. The adduct stabilized the ARP and delayed its decomposition and inhibited the downstream reactions toward browning. After the ARP was depleted, ellagic acid also showed an effect on scavenging some short-chain dicarbonyls which contributed to the inhibition of Maillard browning.

In-silico prediction and modeling of the quorum sensing luxs protein and inhibition of AI-2 biosynthesis in aeromonas hydrophila

luxS is conserved in several bacterial species, including A. hydrophila, which causes infections in prawn, fish, and shrimp, and is consequently a great risk to the aquaculture industry and public health. luxS plays a critical role in the biosynthesis of the autoinducer-2 (AI-2), which performs wide-ranging functions in bacterial communication, and especially in quorum sensing (QS). The prediction of a 3D structure of the QS-associated LuxS protein is thus essential to better understand and control A. hydrophila pathogenecity. Here, we predicted the structure of A. hydrophila LuxS and characterized it structurally and functionally with in silico methods. The predicted structure of LuxS provides a framework to develop more complete structural and functional insights and will aid the mitigation of A. hydrophila infection, and the development of novel drugs to control infections. In addition to modeling, the suitable inhibitor was identified by high through put screening (HTS) against drug like subset of ZINC database and inhibitor ((-)-Dimethyl 2,3-O-isopropylidene-L-tartrate) molecule was selected based on the best drug score. Molecular docking studies were performed to find out the best binding affinity between LuxS homologous or predicted model of LuxS protein for the ligand selection. Remarkably, this inhibitor molecule establishes agreeable interfaces with amino acid residues LYS 23, VAL 35, ILE76, and SER 90, which are found to play an essential role in inhibition mechanism. These predictions were suggesting that the proposed inhibitor molecule may be considered as drug candidates against AI-2 biosynthesis of A. hydrophila. Therefore, (-)-Dimethyl 2,3-O-isopropylidene-L-tartrate inhibitor molecule was studied to confirm its potency of AI-2 biosynthesis inhibition. The results shows that the inhibitor molecule had a better efficacy in AI-2 inhibition at 40 μM concentration, which was further validated using Western blotting at a protein expression level. The AI-2 bioluminescence assay showed that the decreased amount of AI-2 biosynthesis and downregulation of LuxS protein play an important role in the AI-2 inhibition. Lastly, these experiments were conducted with the supplementation of antibiotics via cocktail therapy of AI-2 inhibitor plus OXY antibiotics, in order to determine the possibility of novel cocktail drug treatments of A. hydrophila infection.