154461-64-0

Basic information

• Product Name: Methyl 5-O-feruloylquinate
• Synonyms: Methyl 5-O-feruloylquinate;(1R,3R,4S,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: 154461-64-0
• Molecular Formula: C18H22O9
• Molecular Weight: 382.36188
• Mol File: 154461-64-0.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 5-O-feruloylquinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-O-feruloylquinate(154461-64-0)
• EPA Substance Registry System: Methyl 5-O-feruloylquinate(154461-64-0)

Safety Data

• Hazardous Substances Data: 154461-64-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Methyl 5-O-feruloylquinate is used as a pharmaceutical agent for its potential antioxidant and anti-inflammatory properties. It is being studied for its ability to promote human health and as a natural alternative to synthetic antioxidants.
Used in Cosmetic Applications:
In the cosmetic industry, Methyl 5-O-feruloylquinate is used as an active ingredient for its antioxidant and anti-inflammatory properties. It can help protect the skin from oxidative stress and inflammation, contributing to healthier and more youthful-looking skin.
Used in Food Industry:
Methyl 5-O-feruloylquinate is used as a natural preservative in the food industry. Its antioxidant properties can help extend the shelf life of food products by preventing oxidation and spoilage.
Used in Nutraceutical Applications:
As a nutraceutical, Methyl 5-O-feruloylquinate is used to support overall health and well-being. Its potential antioxidant and anti-inflammatory properties can contribute to a range of health benefits, including improved immune function and reduced inflammation.
Used in Research:
Methyl 5-O-feruloylquinate is used as a subject of research in the fields of bioactive compounds, natural products, and plant metabolites. Its potential health benefits and applications in various industries make it an important compound for further investigation and development.

Upstream product

• 121-33-5 vanillin 
• 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 
• 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.