35949-53-2

Basic information

• Product Name: (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE
• Synonyms: (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE;(-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE 99+%;(1R,2R,4S,6R)-2,4-Dihydroxyspiro[7,9-dioxabicyclo[4.3.0]nonane-8,1'-cyclohexane]-4-carboxylic acid-4,2-lactone;(3aR)-3a,4,8,8aα-Tetrahydro-7α-hydroxyspiro[4β,7-methano-1,3-dioxolo[4,5-c]oxepin-2,1'-cyclohexane]-6(7H)-one;(3aβ,7aβ)-5,7β-Dihydroxyhexahydrospiro[1,3-benzodioxole-2,1'-cyclohexane]-5β-carboxylic acid 5,7-lactone;(-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LAC
• CAS NO: 35949-53-2
• Molecular Formula: C₁₃H₁₈O₅
• Molecular Weight: 254.28
• Mol File: 35949-53-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 140.8-141.3 °C
• Boiling Point: 453.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 12.54±0.20(Predicted)
• CAS DataBase Reference: (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE(35949-53-2)
• EPA Substance Registry System: (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE(35949-53-2)

Safety Data

• Hazardous Substances Data: 35949-53-2(Hazardous Substances Data)

Usage

General Description

(-)-4,5-O-Cyclohexylidenequinic acid lactone is a chemical compound that belongs to the class of quinic acid derivatives. It is a cyclic lactone derivative of quinic acid, and is often used as a building block in the synthesis of various pharmaceutical and biologically active compounds. (-)-4,5-O-CYCLOHEXYLIDENEQUINIC ACID LACTONE has been studied for its potential applications in the field of medicinal chemistry, particularly for its role in the development of new drugs and treatments. Its unique structure and properties make it a valuable tool for chemical synthesis, and it has the potential to contribute to advancements in drug discovery and development. Overall, (-)-4,5-O-Cyclohexylidenequinic acid lactone is a versatile and important chemical compound with potential applications in various fields, particularly in the pharmaceutical industry.

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 108-94-1 cyclohexanone 
• 933-40-4 cycloxexanone dimethyl ketal 
• 168784-18-7 C₁₃H₂₀O₆ 
• 901129-88-2 methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate 
• 191916-39-9 methyl (-)-quinate 
• 135711-62-5 methyl quinicate 
• 213250-58-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester 

Downstream Products

• 160341-65-1 C₂₀H₂₄O₅ 
• 160341-72-0 C₂₂H₂₇ClO₅ 
• 219547-38-3 (3R,5R)-1-Benzyloxy-3,4,5-trihydroxy-cyclohexanecarboxylic acid amide 
• 219547-37-2 C₂₀H₂₇NO₅ 
• 1899-30-5 trans-3-p-coumaroylquinic acid 
• 25514-46-9 (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid 

Relevant articles and documents

Construction of the Bicyclic Core Structure of the Enediyne Antibiotic Esperamicin-A1 in Either Enantiomeric Form from (-)-Quinic Acid

Employed as a common chiral starting material, (-)-quinic acid (7) was converted in a concise manner to both enantiomers of the β,γ-unsaturated ketone 12.On the one hand, (+)-12 was obtained by stereospecific borohydride reduction of the conjugated ketone

Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid

(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.

Stereoselective synthesis of the halaven C14-C26 fragment from D-quinic acid: Crystallization-induced diastereoselective transformation of an α-methyl nitrile

Crystallization-induced diastereoselective transformation (CIDT) of an α-methyl nitrile completes an entirely non-chromatographic synthesis of the halichondrin B C14-C26 stereochemical array. The requisite α-methyl nitrile substrate is derived from D-quinic acid through a series of substrate-controlled stereoselective reactions via a number of crystalline intermediates that benefit from a rigid polycyclic template. Therefore, all four stereogenic centers in the Halaven C14-C26 fragment were derived from the single chiral source D-quinic acid.

Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives

Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxiciti