1,5-Dicaffeoylquinic acid (CED0010854)

Record Information

Version

1.0

Creation Date

2016-05-22 07:09:44 UTC

Update Date

2026-03-27 01:14:10 UTC

Accession Number

CHEM020503

Identification

Common Name

1,5-Dicaffeoylquinic acid

Class

Small Molecule

Description

1,5-Dicaffeoylquinic acid (C25H24O12) is a chemical compound found in several recorded sources. These include food, food processing, and cookware, specifically in the preparation of wine or sparkling wine and the preparation of vinegar. Additionally, it is associated with household cleaning and consumer products, including pipe accessories, other smoking requisites, and tobacco product moisture control. 1,5-Dicaffeoylquinic acid belongs to the alcohols and polyols, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 516.46 g/mol, 1,5-Dicaffeoylquinic acid is a heavy molecule.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,5-Dicaffeoylquinate	Generator
Cynarex	MeSH
Cinarin	MeSH
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer	MeSH
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)	MeSH
Cinarina	MeSH
Cynarix	MeSH
Cynarine	MeSH
Listrocol	MeSH
Nivellipid	MeSH
Phemocil	MeSH
Listricol	MeSH
Cynarin	MeSH
Cinarine	MeSH
1,5-Dicaffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Mass

516.455 g/mol

Monoisotopic Mass

516.127 g/mol

CAS Registry Number

30964-13-7

IUPAC Name

(1R,3R,4S,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

SMILES

[H][C@@]1(O)C[C@](C[C@@]([H])(OC(=O)C=CC2=CC(O)=C(O)C=C2)[C@@]1([H])O)(OC(=O)C=CC1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/t19-,20-,23+,25-/m1/s1

InChI Key

YDDUMTOHNYZQPO-GCBRTHAASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	49.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02tj-0609440000-99cfebe1fccd40b61c09	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01p9-0908300000-bbfcd26f89596fca48d4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01y6-0912200000-1350f5b02de7fb2e74d9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gb9-0519570000-c925c7cfe9b736c3e6b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0r99-0739200000-81ff8f739c18fd81aee4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06vi-0914000000-01a86eada0ff408511a2	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8823.0	Log mg/kg	[5000:16000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
568	Tobacco Product Moisture Control	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	0.934191
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P07943	Rattus norvegicus	Predicted (SEA)	1.47914
Click to view 3D structure	Gag-Pol polyprotein	Q7ZJM1	Human immunodeficiency virus 1	Predicted (SEA)	3.81461
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	13.3122
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	35.6549
Click to view 3D structure	Beta-secretase 1	P56817	Humans	Predicted (SEA)	66.8725
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P12527	Rattus norvegicus	Predicted (SEA)	20.5522
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	26.1573
Click to view 3D structure	Xanthine dehydrogenase/oxidase	P80457	Bos taurus	Predicted (SEA)	10.821
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	115.762
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	72.2441
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	37.9126
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	128.763
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	54.5723
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	55.5065
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	117.552
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	153.207
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	53.0153
Click to view 3D structure	Nuclear receptor subfamily 0 group B member 2	Q15466	Humans	Predicted (SEA)	0.934191
Click to view 3D structure	Alpha-synuclein	P37840	Humans	Predicted (SEA)	5.60514
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	237.907
Click to view 3D structure	Large T antigen	P03070	Simian virus 40	Predicted (SEA)	14.48
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	837.424
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	233.937