3-O-Feruloylquinic acid
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Basic information
- CAS
1899-29-2- Standard SMILES
COc1cc(/C=C/C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)ccc1O- InChIKey
RAGZUCNPTLULOL-KJJWLSQTSA-N- Molecular formula
- C17H20O9
- Average molar mass
- 368.3 g/mol
- Monoisotopic mass
- 368.11073221
Overview
3-O-feruloyl-D-quinic acid is a quinic acid that is the 3-O-feruloyl derivative of D-quinic acid. It has a role as a plant metabolite. It is a quinic acid and an enoate ester. It is functionally related to a (-)-quinic acid and a trans-ferulic acid.
Names & identifiers
- Preferred name
- 3-O-Feruloylquinic acid
- IUPAC
- (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
- English name
- 3-O-(E)-Feruloylquinic Acid
- Molecular formula
- C17H20O9
- Molecular weight
- 368.34
Names & synonyms
3-O-Feruloylquinic acid(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid1899-29-2(1S,3R,4R,5R)-1,3,4-trihydroxy-5-((E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl)oxy-cyclohexanecarboxylic acid(1S,3R,4R,5R)-1,3,4-trihydroxy-5-((E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl)oxycyclohexane-1-carboxylic acid(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylic acidRefChem:50454462929-69-55-O-(E)-Feruloylquinic Acid5-O-Feruloylquinic acid3-O-feruloyl-D-quinic acidC02572
Show more names
3-O-(E)-Feruloylquinic AcidCyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (1S,3R,4R,5R)-
(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-(((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)cyclohexane-1-carboxylic acid(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid5-Feruoylquinic acid(1S,3R,4S,5R)-1,3,5-Trihydroxy-4-(((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)cyclohexanecarboxylic Acid; [1S-[1a,3a,4a,5ss(E)]]-1,3,4-Trihydroxy-5-[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic Acid;3-Ferulylquinic acid5-feruoyl quinic acid3-O-ferulicoylquinic acid3-O-feruloyl quinic acid
Properties
Computed structural propertiesFilling in
- XLogP
- -0.1
- Topological polar surface area
- 154 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 548
Experimental & physicochemical properties
Melting Point196 - 197 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 135 °C · >135°C (dec.)
- Boiling point
- 629.4 · 629.4±55.0 °C(Predicted)
- Density
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 3.9 · 3.90±0.50(Predicted)
- form
- Solid
- color
- White to Light Yellow
- Stability
- Hygroscopic
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Uses3-O-(E)-Feruloylquinic Acid is a phenolic acid with potential antioxidant and antifungal activities. Secondary metabolite in the coffee brewing process.
Additional notes
DefinitionChEBI: 3-O-feruloyl-D-quinic acid is a quinic acid that is the 3-O-feruloyl derivative of D-quinic acid. It has a role as a plant metabolite. It is a quinic acid and an enoate ester. It is functionally related to a (-)-quinic acid and a ferulic acid.
Related reactions
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Compound notes
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