665-27-0

Basic information

• Product Name: 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)-
• CAS NO: 665-27-0
• Molecular Formula: C7H10O5
• Molecular Weight: 174.153
• Mol File: 665-27-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 185-187 °C
• Boiling Point: 395.4±42.0 °C(Predicted)
• Density: 1.810±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)-(665-27-0)
• EPA Substance Registry System: 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)-(665-27-0)

Safety Data

• Hazardous Substances Data: 665-27-0(Hazardous Substances Data)

Usage

Uses

(-)-Quinic Acid γ-Lactone is an intermediate in the synthesis of 4-O-(E)-Feruloylquinic Acid (F308985). 4-O-(E)-Feruloylquinic Acid is a phenolic acid with potential antioxidant and antifungal activities. Secondary metabolite in the coffee brewing process.

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 50459-25-1 (-)-methyl 4-epi-quinate 
• 77-95-2 (1R,3R,4R,5R)-(-)-quinic acid 
• 216662-57-6 (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 
• 164029-68-9 (1S,3R,4R,5R)-3,4-O-Cyclopentylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 

Downstream Products

• 1151911-12-4 (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-cyclohexane-carboxylic acid propylamide 
• 1151911-33-9 KZ-45 
• 1151911-17-9 C₁₉H₃₇NO₅ 
• 1151911-20-4 C₂₃H₄₅NO₅ 
• 1151911-27-1 C₁₄H₂₆N₂O₇ 
• 1151911-23-7 KZ-39 
• 1191428-31-5 C₁₀H₁₉NO₅ 
• 1151911-29-3 C₉H₁₈N₂O₅ 
• 1352319-06-2 (1R,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohexanecarboxylate 
• 1352319-09-5 C₂₇H₃₈O₆Si 
• 1352319-07-3 (1S,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3,5-dihydroxycyclohexanecarboxylate 
• 1352319-08-4 3,3'-(((1R,2S,3R,5S)-2,5-bis(benzyloxy)-5-((benzyloxy)carbonyl)cyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid) 
• 1352319-04-0 3,3'-(((1R,2S,3R,5S)-5-carboxy-2,5-dihydroxycyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid) 
• 2450-53-5 3,5-di-O-caffeoylquinic acid 

Relevant articles and documents

Identification and Quantitation of Reaction Products from Quinic Acid, Quinic Acid Lactone, and Chlorogenic Acid with Strecker Aldehydes in Roasted Coffee

To gain comprehensive insight into the interactions of key coffee odorants, like the Strecker aldehydes, acetaldehyde, propanal, methylpropanal, 2- and 3-methylbutanal, and methional, and the nonvolatile fraction of coffee, an untargeted metabolomics approach was applied. Ultra performance liquid chromatography (UPLC)-time of flight (TOF)-mass spectrometry (ESI-) profiling followed by statistical data analysis revealed a marker substance for a coffee beverage spiked with acetaldehyde with an accurate mass of 217.0703 [M - H]-. This compound could be identified as a reaction product of quinic acid (QA) and acetaldehyde linked by acetalization at the cis-diol function of QA. Consequently, the acetalization of aldehydes, QA, 5-O-caffeoyl quinic acid (CQA), and quinic acid γ-lactone (QAL) was investigated by means of model reactions, followed by synthesis, isolation, and structure elucidation via UPLC-TOF-MS and 1D and 2D NMR techniques. UHPLC-MS/MSMRM screening and the quantification of aldehyde adducts in coffee beverages revealed the presence of QA/acetaldehyde, -/propanal, -/methylpropanal, and -/methional reaction products and CQA/acetaldehyde, -/propanal, -/methylpropanal, -/2- and 3-methylbutanal, and -/methional and QAL/acetaldehyde adducts for the first time, in concentrations of 12-270 μg/L for QA/aldehydes, 5-225 μg/L for CQA/aldehydes, and 62-173 μg/L for QAL/acetaldehyde. The sensory characterization of the identified compounds showed bitter taste recognition thresholds of 48-297 μmol/L for CQA adducts and 658 μmol/L for QAL/acetaldehyde, while the QA adducts showed no bitter taste (2000 μmol/L).

Oral Pharmaceutical Formulation for Weight Loss, Diabetes and Related Disorders

There is disclosed an oral pharmaceutical formulation of bitter compounds that are agonists of taste receptor type 2 (TAS2R) receptors for the function of appetite suppression for the treatment of obesity. More specifically, the present disclosure provide

Biomass-Based and Oxidant-Free Preparation of Hydroquinone from Quinic Acid

A biomass-based route to the preparation of hydroquinone starting from the renewable starting material quinic acid is described. Amberlyst-15 in the dry form promoted the one-step formation of hydroquinone from quinic acid in toluene without any oxidants or metal catalysts in 72 % yield. Several acidic polymer-based resins and organic acids as promoters as well as a variety of reaction conditions were screened including temperature, concentration and low- and high-boiling-point solvents. A 1:4 (w/w) ratio of quinic acid/Amberlyst-15 was determined to be optimal to promote hydroquinone formation with only traces of a dimeric side-product. A mechanism has been proposed based on the decarbonylation of protonated quino-1,5-lactone that is supported by experimental and computational calculation data.