Cas no 1108200-72-1 (4-coumaroylquinic acid)

4-coumaroylquinic acid structure
4-coumaroylquinic acid structure
Product Name:4-coumaroylquinic acid
CAS No:1108200-72-1
MF:C16H18O8
MW:338.309325695038
CID:2011570
PubChem ID:5281766
Update Time:2025-04-21

4-coumaroylquinic acid Chemical and Physical Properties

Names and Identifiers

    • 4-coumaroylquinic acid
    • 4-O-(trans-p-coumaroyl)quinic acid
    • 4-O-p-coumaroylquinic acid
    • 4-p-coumaroylquinic acid
    • 4-pCoQA
    • 4-trans-coumaroylquinic acid
    • trans-4-p-coumaroylquinic acid
    • NCGC00380946-01
    • CHEBI:176887
    • AKOS040734777
    • 4-o-Coumaroylquinic acid
    • (1S,3R,4S,5R)-1,3,5-trihydroxy-4-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
    • 53539-37-0
    • SCHEMBL21381742
    • 4-p-Cqa
    • NCGC00380946-01_C16H18O8_(1S,3R,4S,5R)-1,3,5-Trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]oxy}cyclohexanecarboxylic acid
    • MEGxp0_000071
    • FS-8566
    • 93451-44-6
    • CYCLOHEXANECARBOXYLIC ACID, 1,3,5-TRIHYDROXY-4-(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1.ALPHA.,3R,4.ALPHA.,5R)-
    • K4772MBI5O
    • 1108200-72-1
    • UNII-K4772MBI5O
    • Cyclohexanecarboxylic acid, 1,3,5-trihydroxy-4-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (1alpha,3R,4alpha,5R)-
    • (3R,5R)-1,3,5-trihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
    • DTXSID701341733
    • CHEBI:1945
    • (3R,5R)-1,3,5-trihydroxy-4-(((E)-3-(4-hydroxyphenyl)acryloyl)oxy)cyclohexane-1-carboxylic acid
    • GLXC-19217
    • HY-N12980
    • CS-1099793
    • Inchi： 1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(20)24-14-11(18)7-16(23,15(21)22)8-12(14)19/h1-6,11-12,14,17-19,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14?,16?/m1/s1
    • InChI Key： XWRHBGVVCOSNKO-OPGYGNEESA-N
    • SMILES： O(C(/C=C/C1C=CC(=CC=1)O)=O)C1[C@@H](CC(C(=O)O)(C[C@H]1O)O)O

Computed Properties

  • Exact Mass: 338.10016753g/mol
  • Monoisotopic Mass: 338.10016753g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 24
  • Rotatable Bond Count: 5
  • Complexity: 482
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.1
  • Topological Polar Surface Area: 145?2

4-coumaroylquinic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 2

Reaction Conditions
1.1 Reagents: Pyridine ,  (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ;  24 h, rt
1.2 Reagents: Water ;  cooled
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 3

Reaction Conditions
1.1 Catalysts: Trimethyl orthoformate ,  (-)-Camphorsulfonic acid ;  15 h, reflux
2.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  24 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 4

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 5

Reaction Conditions
1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  24 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 6

Reaction Conditions
1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  30 min, 0 °C; 1 h, rt
2.1 Reagents: Pyridine ,  (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ;  24 h, rt
2.2 Reagents: Water ;  cooled
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

Production Method 7

Reaction Conditions
1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Toluene ;  2 h, -5 °C; overnight, rt
2.1 Reagents: Pyridine ,  (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ;  24 h, rt
2.2 Reagents: Water ;  cooled
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 d, rt
Reference
Synthesis of p-coumaroylquinic acids and analysis of their interconversion
Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

4-coumaroylquinic acid Raw materials

4-coumaroylquinic acid Preparation Products

4-coumaroylquinic acid Related Literature

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