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

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

Used in Pharmaceutical Industry:
6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)is used as an intermediate in the synthesis of 4-O-(E)-Feruloylquinic Acid (F308985), a phenolic acid with potential antioxidant and antifungal activities. This makes it valuable in the development of new drugs and treatments.
Used in Coffee Brewing Process:
In the coffee industry, 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)serves as a secondary metabolite in the coffee brewing process. Its presence contributes to the unique flavor and aroma profiles of coffee beverages.
Used in Antioxidant Applications:
Due to its potential antioxidant properties, 6-Oxabicyclo[3.2.1]octan-7-one, 1,3,4-trihydroxy-, (1S,3R,4R,5R)can be utilized in various applications where antioxidants are needed, such as in food preservation, cosmetic formulations, and health supplements to protect against oxidative stress and promote overall health.

Upstream product

• 77-95-2 D-(-)-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 
• 50459-25-1 (-)-methyl 4-epi-quinate 
• 77-95-2 (1R,3R,4R,5R)-(-)-quinic acid 
• 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

• 185810-83-7 (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone 
• 189366-41-4 (2R)-2-fluoro-3-dehydroquinic acid 
• 189366-39-0 (2R)-2-bromo-3-dehydroquinic acid 
• 185810-87-1 (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 
• 185810-84-8 (1S,3R,4R,5R)-3-Benzyloxy-1,4-dimethoxy-6-oxa-bicyclo[3.2.1]octan-7-one 
• 185810-88-2 (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 
• 185810-89-3 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 
• 185810-90-6 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-chloro-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 
• 185810-91-7 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-iodo-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 
• 163217-17-2 (1S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohexanecarboxylic acid methyl ester 
• 163217-21-8 (1R,3R,5R)-3-(4-Bromo-benzenesulfonyloxy)-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid methyl ester 
• 1151911-33-9 KZ-45 
• 1151911-17-9 C₁₉H₃₇NO₅ 
• 1151911-20-4 C₂₃H₄₅NO₅ 

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 FORMULATIONS OF BITTER COMPOUNDS FOR PULMONARY HYPERTENSION

There is disclosed an oral pharmaceutical formulation of bitter compounds that are agonists of TAS2R receptors for the treatment of pulmonary hypertension (PAH). More specifically, there is disclosed a PAH oral formulation comprising a bitter agent selected from the group consisting of 3-caffeoylquinic-1,5-lactone (3-CQL), chlorogenic acid (CGA), denatonium benzoate (DB), denatonium chloride (DC), denatonium saccharide (DS), denatonium acetate (DA), and combinations thereof and a PDE-5 inhibitor.

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

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.

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.

Quinic acid lactone derivative preparation method

The present invention relates to a quinic acid lactone derivative preparation method, which comprises: in an organic solvent, carrying out a reaction with a compound 1 to obtain a compound 2. According to the method of the present invention, the solubility of the reactant in the solvent is increased so as to substantially improve the yield of the product and provide convenience and economy. The structures of the compounds 1 and 2 are defined in the specification.

Synthesis of mono-, di-, and tri-3,4-dimethoxycinnamoyl-1,5-γ- quinides

Tri-3,4-dimethoxycinnamoyl-1,5-γ-quinide was synthesized and fully characterized by a direct synthesis from quinic acid and a large excess of 3,4-dimethoxycinnamoyl chloride. Mono-and di-3,4-dimethoxycinnamoyl-1,5-γ- quinides were also obtained from the direct coupling of 1,5-γ-quinide and 3,4-dimethoxycinnamoyl chloride in different molar ratios. Moreover, a hypothetical mechanism of the direct lactonization is proposed. Mono-, di-, and tri-3,4-dimethoxycinnamoyl-1,5-γ-quinides have been synthesized from 1,5-γ-quinide and 3,4-dimethoxycinnamoyl chloride in different molar ratios. The only triester quinide was also easily obtained by a direct synthesis from D-(-)-quinic acid in the presence of an excess of the acyl chloride. Copyright

Syntheses of 3-, 4-, and 5-O-feruloylquinic acids

The efficient synthesis of 3-, 4-, and 5-O-feruloylquinic acids starting from d-(-)-quinic acid is described. Esterification of suitably protected quinic acid derivatives with 3-(4-acetoxy-3-methoxyphenyl)-acryloyl chloride and subsequent hydrolysis of al

Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.

1-Desoxy-2-Methylene-19-Nor-Vitamin D Analogs and Their Uses

This invention discloses 1-desoxy-2-methylene-19-nor-vitamin D analogs, and specifically (20S)-25-hydroxy-1-desoxy-2-methylene-19-nor-vitamin D3 and pharmaceutical uses therefor. This compound exhibits relatively high binding activity and prono