191916-39-9

Basic information

• Product Name: methyl (-)-quinate
• Synonyms: methyl (-)-quinate
• CAS NO: 191916-39-9
• Molecular Weight: 206.196
• Mol File: 191916-39-9.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: methyl (-)-quinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (-)-quinate(191916-39-9)
• EPA Substance Registry System: methyl (-)-quinate(191916-39-9)

Safety Data

• Hazardous Substances Data: 191916-39-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 77-95-2 D-(-)-quinic acid 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 863983-56-6 (1S,3R,4R,5S,6S)-4-(tert-butyldimethylsiloxy)-6-chloro-1,5-dihydroxycyclohexane-1,3-carbolactone 
• 215929-07-0 (1R,4S,4aR,6R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester 
• 215929-09-2 (1R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester 
• 215929-06-9 (1R,4S,4aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester 
• 171824-23-0 (-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one 
• 74-88-4 methyl iodide 
• 215929-14-9 (3aR,5S,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 154418-15-2 3-O-caffeoylquinic acid methyl ester 
• 154418-15-2 3-O-feruloylquinic acid methyl ester 
• 215929-10-5 (1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 215929-13-8 (3aS,4S,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-4-(imidazole-1-carbothioyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 

Downstream Products

• 143536-04-3 methyl 4-O-butanoylquinate 
• 77-95-2 D-(-)-quinic acid 
• 86632-03-3 3,4,5-tri-O-caffeoyl-quinic acid 
• 1899-30-5 3-O-p-coumaroylquinic acid 
• 135711-62-5 methyl quinicate 
• 213250-59-0 methyl (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylate 
• 99-94-5 p-Toluic acid 

Relevant articles and documents

Butane 2,3-bisacetal protection of vicinal diequatorial diols

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A novel stereoselective synthesis of (-)-quinic acid starting from the naturally abundant (-)-shikimic acid

A new stereoselective synthesis of (-)-quinic acid from the naturally abundant (-)-shikimic acid is described. Ethyl shikimate 2 was first prepared in 97% yield via esterification of (-)-shikimic acid according to a previous report. Ester 2 was then transformed into an epimeric mixture of 3,4-O-benzylidene shikimate 3, which was directly converted into compound 4 in 90% yield (over 2 steps from ester 2) via an NBS-mediated acetal ring-opening reaction. Acetylization of the hydroxyl group at the C-5 position of compound 4 gave compound 5 in 98% yield. Compound 5 was transformed into compound 6 in 91% yield via a highly stereoselective Ru-catalyzed dihydroxylation. Subsequently, compound 6 was converted into epoxide 7 in 82% yield via an intramolecular SN2 type substitution. A regioselective epoxide-opening of compound 7 by PPh3-I2 complex furnished an iodo compound 8 in 79% yield. Removal of the iodine atom in compound 8 by Pd/C-catalyzed hydrogenation produced compound 9 in 92% yield. Methanolysis of compound 9 gave methyl quinate 10 in 92% yield. Finally, hydrolysis of compound 10 afforded the targeted compound (-)-quinic acid 1 in 90% yield. The title compound (-)-quinic acid 1 was stereoselectively synthesized through 10 steps starting from (-)-shikimic acid in 38% overall yield.

Non-conventional epimerisation and functionalisation of quinic acid and shikimic acid methyl esters

In a convenient one-pot acetalation procedure using chloral/DCC, methyl (-)-quinate and methyl (-)-shikimate were converted into their 4-epi-derivatives containing a carbamoyl function in 3-position and the trichloroethylidene acetal group in 4,5-position

Quinic acid derivative and preparation method and application thereof

The invention discloses a quinic acid derivative and a preparation method and application thereof. The quinic acid derivative has a structure represented by a formula I, wherein R1, R2 and R3 are OH or AcNH; R1 = OH, R2 = R3 = AcNH, or R2 = OH, R1 = R3 = AcNH, or R3 = OH, R1 = R2 = AcNH; * represents an R configuration or an S configuration; and Ac represents caffeoyl CAc or a derivative caffesulfonyl SAc, and coffee(mono-methyl ester)phosphonyl PAc. The quinic acid derivative has the advantages of mild preparation conditions, simple and safe operation, high product purity and relatively hightotal yield, and the obtained quinic acid derivative can be used for preparing medicaments for treating viral infections, especially for preparing medicaments for treating influenza virus, parainfluenza virus and respiratory syncytial virus infections.

P-TOLUIC ACID PRODUCING METHOD

A method for producing highly pure p-toluic acid by a simple solid-liquid separation operation using as a raw material a substance inducible from a biomass resource and suitable for fermentation production by a microorganism is disclosed. The method for producing p-toluic acid includes: a dehydration reaction step of dehydrating Compound(s) (1)-(4), which are substances inducible from biomass resources and suitable for fermentation production by microorganisms; and a solid-liquid separation step of recovering a solid produced by this dehydration reaction by a simple solid-liquid separation operation.