154418-15-2

Basic information

• Product Name: Methyl 3-O-feruloylquinate
• Synonyms: Methyl 3-O-feruloylquinate;(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]oxy]cyclohexanecarboxylic acid methyl ester
• CAS NO: 154418-15-2
• Molecular Formula: C18H22O9
• Molecular Weight: 382.36188
• Mol File: 154418-15-2.mol

Chemical Properties

• Boiling Point: 553.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 9.74±0.31(Predicted)
• CAS DataBase Reference: Methyl 3-O-feruloylquinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-O-feruloylquinate(154418-15-2)
• EPA Substance Registry System: Methyl 3-O-feruloylquinate(154418-15-2)

Safety Data

• Hazardous Substances Data: 154418-15-2(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
Methyl 3-O-feruloylquinate is used as a natural preservative or flavoring agent in the food industry, leveraging its antioxidant properties to enhance the shelf life and taste of various food products.
Used in Antioxidant Applications:
Due to its potential antioxidant properties, Methyl 3-O-feruloylquinate is being studied for its possible use in various applications where antioxidants are beneficial, such as in health supplements or cosmetics, to protect against oxidative stress and promote overall health.
The exact uses and potential benefits of Methyl 3-O-feruloylquinate are still being researched, but its natural origin and antioxidant properties make it a promising compound for further investigation and potential applications in various industries.

Upstream product

• 115375-24-1 (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid 
• 183625-03-8 methyl (1S,3R,4R,5S,2'S,3'S)-1,3-dihydroxy-4,5-[2,3-dimethoxybutane-2,3-di(yloxy)]cyclohexane-1-carboxylate 
• 183474-88-6 methyl (1S,4S,5R)-1-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohexan-1-carboxylate 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 77-95-2 D-(-)-quinic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 850786-96-8 (E)-3-methoxy-4-allyloxycinnamoyl chloride 
• 1384546-00-2 C₂₄H₃₂O₁₁ 
• 1384545-88-3 C₂₇H₃₆O₁₁ 
• 121-33-5 vanillin 
• 55882-65-0 4-acetoxyferuloyl chloride 
• 191916-39-9 methyl (-)-quinate 
• 186581-53-3 diazomethane 
• 1899-29-2 3-O-feruloyl-D-quinic acid 

Relevant articles and documents

First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates

We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic acid, caffeic acid and ferulic acid. Allyl ether protection of trans-hydroxy cinnamic acids was here introduced to chlorogenic acids synthesis. We show that muco-quinic acid derivatives, which are formally diastereoisomers of chlorogenic acids, can be readily distinguished by their tandem mass spectra. The Royal Society of Chemistry 2012.

How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography-tandemmass spectrometry

The methyl esters of chlorogenic acids, methyl quinates, are widely distributed in plant materials and frequently appear as extraction artifacts in plant samples. This is the first time when liquid chromatography-tandem mass spectrometry methods have been used for the identification and characterization of the methyl quinates. For this purpose, methyl quinates of mono caffeoylquinic acids and mono feruloylquinic acids were synthesized as authentic standards. The methyl quinates of mono and diacyl chlorogenic acids have shown characteristic fragmentation pattern in their tandem mass spectra. MS n+1 spectra of the methyl quinates of diacyl chlorogenic acids were identical to MSn spectra of mono acyl derivatives. These quinates do not produce any methyl quinate peak at m/z 205 if compared with quinic acid peak at m/z 191 in negative ion mode. In the MSn spectra of these quinates, cinnamic acid part or cinnamoyl part was detected as a base peak in negative ionmode. The retention time, order of elution and fragmentation pattern were completely different if compared with LC-MSn methods developed for chlorogenic acids. These LC-MSn methods have been applied for the identification and regioisomeric characterization of the methyl quinates of chlorogenic acids in mate tea and woodruff (Galium odoratum). Twomethyl caffeoylquinates (2 and 4) were identified asmethyl 3-caffeoylquinate andmethyl 5-caffeoylquinate. Copyright

A novel efficient and versatile route to the synthesis of 5-O-feruloylquinic acids

A novel synthesis of 5-O-feruloylquinic acid, a polyphenolic compound found in coffee beans, and its methyl ester derivative has been optimized. The sequence involves 6 steps and is compatible with the preparation of potential human metabolites of these c

PHENOLIC CONSTITUENTS OF PHELLODENDRON AMURENSE BARK

Glycosides of (+/-)-5,5'-dimethoxyariciresinol, 2-(p-hydroxy-phenyl)-ethanol and N-methylhigenamine were isolated from the dried bark of Phellodendron amurense, together with nine phenolic compounds.