Cas no 87099-71-6 (5-O-Coumaroylquinic Acid)

5-O-Coumaroylquinic Acid structure
5-O-Coumaroylquinic Acid structure
Product Name:5-O-Coumaroylquinic Acid
CAS No:87099-71-6
MF:C16H18O8
MW:338.309325695038
CID:582398
PubChem ID:9945785
Update Time:2024-10-26

5-O-Coumaroylquinic Acid Chemical and Physical Properties

Names and Identifiers

    • Cyclohexanecarboxylic acid,1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-,(1R,3R,4S,5R)-
    • 1AF7V9VW0S
    • o-Coumaroylquinic acid
    • 3-p-coumaroylquinic acid
    • 3-O-Coumaroylquinic acid
    • 3-O-p-Coumaroylquinic acid
    • 3-p-Coqa
    • p-Coumaroyl 5-O-quinate
    • 5-p-Coumaroylquinic acids
    • 5-O-p-Coumaroylquinic acid
    • Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (1R,3R,4S,5R)-
    • 1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9CI
    • 870
    • (1R,3R,4S,5R)-1,3,4-Trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]cyclohexanecarboxylic acid (ACI)
    • Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)- (9CI)
    • Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [1R-[1α,3β,4α,5α(E)]]- (ZCI)
    • 5-O-Coumaroylquinic acid
    • 32451-86-8
    • (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid
    • UNII-1AF7V9VW0S
    • NCGC00384821-01
    • 87099-71-6
    • DTXSID301344004
    • 5-Coumaroyl quinic acid
    • AKOS040740142
    • (1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
    • CHEBI:75499
    • CHEBI:167530
    • (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
    • SCHEMBL21240786
    • FS-8565
    • GLXC-19216
    • Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (1R,3R,4S,5R)-
    • 5-O-Coumaroylquinic Acid
    • Inchi： 1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1
    • InChI Key： BMRSEYFENKXDIS-QHAYPTCMSA-N
    • SMILES： O([C@H]1[C@@H](O)[C@H](O)C[C@](O)(C(=O)O)C1)C(=O)/C=C/C1C=CC(O)=CC=1

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: 496
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.1
  • Topological Polar Surface Area: 145

5-O-Coumaroylquinic Acid Pricemore >>

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5-O-Coumaroylquinic Acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
1.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ,  Water ;  21 h, rt
1.2 Reagents: Sodium bisulfate Solvents: Water ;  neutralized, rt
2.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
2.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
3.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 3

Reaction Conditions
1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ;  21 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ,  Water ;  21 h, rt
2.2 Reagents: Sodium bisulfate Solvents: Water ;  neutralized, rt
3.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 4

Reaction Conditions
1.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  2 h, 80 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
3.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ;  75 min, rt
1.2 Reagents: Sodium bisulfate ;  neutralized, rt
1.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  2 h, 80 °C
1.4 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
3.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 6

Reaction Conditions
1.1 Reagents: Benzene, diethenyl-, polymer with ethenylbenzene and ethenylethylbenzene, sulfon… Solvents: Methanol ;  90 h, reflux
2.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ;  21 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ;  rt
3.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ,  Water ;  21 h, rt
3.2 Reagents: Sodium bisulfate Solvents: Water ;  neutralized, rt
4.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 7

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 8

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

Production Method 9

Reaction Conditions
1.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
1.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
2.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 10

Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
2.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
2.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
3.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 11

Reaction Conditions
1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  25 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ;  75 min, rt
2.2 Reagents: Sodium bisulfate ;  neutralized, rt
2.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  2 h, 80 °C
2.4 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
4.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 12

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ;  75 min, rt
1.2 Reagents: Sodium bisulfate ;  neutralized, rt
2.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  2 h, 80 °C
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
4.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 13

Reaction Conditions
1.1 Reagents: Trimethyl orthoformate ,  (-)-Camphorsulfonic acid Solvents: Methanol ;  45 h, 85 °C
2.1 Reagents: Imidazole Solvents: Dimethylformamide ;  25 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ;  rt
3.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ;  75 min, rt
3.2 Reagents: Sodium bisulfate ;  neutralized, rt
3.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ;  2 h, 80 °C
3.4 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid ,  Tetrahydrofuran ;  13 h, rt
4.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
5.1 Reagents: Tosyl chloride ,  Diisopropylethylamine Solvents: 1,2-Dichloroethane ;  30 min, rt
5.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ;  2 h, 40 °C
5.3 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Pentamethylbenzene ,  Boron trichloride Solvents: Dichloromethane ;  10 min, -40 °C; 3 h, -40 °C → 0 °C
6.2 Reagents: Water
Reference
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

Production Method 14

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 15

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 16

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 17

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 18

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

5-O-Coumaroylquinic Acid Raw materials

5-O-Coumaroylquinic Acid Preparation Products

5-O-Coumaroylquinic Acid Related Literature

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