1-Caffeoylquinic acid

Base Information

• Chemical Name: 1-Caffeoylquinic acid
• CAS No.: 928005-87-2
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.314
• UNII: 8WO78APH4R
• DSSTox Substance ID: DTXSID001308334
• Nikkaji Number: J1.315.756A
• Wikidata: Q27271129,Q104666999
• Mol file: 928005-87-2.mol

Synonyms:1-Caffeoylquinic acid;1241-87-8;1-O-caffeoylquinic acid;trans-1-o-Caffeoylquinic acid;928005-87-2;1-Cqa;8WO78APH4R;NPLC-0528;(3R,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxycyclohexane-1-carboxylic acid;Cyclohexanecarboxylic acid, 1-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (-)-, 1-(3,4-dihydroxycinnamate);Cyclohexanecarboxylic acid, 1-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3,4,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;1-Caffeoyl quinic acid;Quinic acid, 1-caffeoyl-;UNII-8WO78APH4R;Quinic acid, 1-caffeoyl-, E-;SCHEMBL18180785;ACon1_000282;1-O-(trans-caffeoyl)quinic acid;CHEBI:136555;DTXSID001308334;HY-N0460;AKOS025402172;AKOS040760125;AC-6023;NCGC00180712-01;MS-25508;PD125742;CS-0008987;2848CBC5-0661-43ED-9EB3-3CDD3AB3BCCD;Q27271129;797FE6FE-1329-4C90-9B0E-B583676AD409;(1S,3R,4S,5R)-1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylic acid;CYCLOHEXANECARBOXYLIC ACID, 1-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-;Cyclohexanecarboxylic acid, 1-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3,4,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;CYCLOHEXANECARBOXYLIC ACID, 1-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-;NCGC00180712-02!(3R,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxycyclohexane-1-carboxylic acid

Chemical Property of 1-Caffeoylquinic acid

Chemical Property:

• XLogP3: -0.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 354.09508215
• Heavy Atom Count: 25
• Complexity: 520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O)O
• Isomeric SMILES: C1[C@H](C([C@@H](CC1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O)O

Technology Process of 1-Caffeoylquinic acid

There total 5 articles about 1-Caffeoylquinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(E)-3-(3,4-Diacetoxy-phenyl)-acrylic acid (1R,2R,6R,8S)-4,4-dimethyl-9-oxo-3,5,10-trioxa-tricyclo[6.2.1.02,6]undec-8-yl ester → 1-O-(trans-caffeoyl)quinic acid (928005-87-2)

Guidance literature:

(E)-3-(3,4-Diacetoxy-phenyl)-acrylic acid (1R,2R,6R,8S)-4,4-dimethyl-9-oxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl ester; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 5h;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 17h;

DOI:10.1002/1099-0690(200107)2001:14<2735::AID-EJOC2735>3.0.CO;2-I

Reference yield:

1,3-di-O-caffeoylquinic acid (212891-05-9) → 1-O-(trans-caffeoyl)quinic acid (928005-87-2)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 2h;

DOI:10.1021/jf050046h

Reference yield:

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2) → 1-O-(trans-caffeoyl)quinic acid (928005-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 58 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / 20 °C

2.1: LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C

2.2: 79 percent / HCl / tetrahydrofuran; H₂O / 17 h / 20 °C

With pyridine; dmap; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/1099-0690(200107)2001:14<2735::AID-EJOC2735>3.0.CO;2-I

upstream raw materials:

1,3-di-O-caffeoylquinic acid

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

(E)-3,4-di-O-acetylcaffeoyl chloride