cynarine
quinic acid 1,5-dicaffeic ester
Identification
| Name | cynarine |
| IUPAC | (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid |
| CAS Number | 30964-13-7 |
| FDA UNII | 85D81U9JAV |
| Molecular Formula | C25 H24 O12 |
| Molecular Weight | 516.45668000 |
| MDL Number | MFCD11112054 |
| Nikkaji Number | J354.360I |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 819.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 533.00 °F. TCC ( 278.10 °C. ) (est) |
| logP (o/w) | 1.640 (est) |
| Soluble in | water, 1329 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for cynarine usage levels up to | not for fragrance use. |
| Recommendation for cynarine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
cinarin
cinarine
cyclohexanecarboxylic acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-
cynarin
1,5-
dicaffeoyl qunic acid
1,5-
dicaffeoylqunic acid
(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-
dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
listrocol
nivellipid
phemocil
plemocil
quinic acid 1,5-dicaffeic ester
PubMed:
[Regulation of syringin, chlorogenic acid and 1,5-dicaffeoylquinic acid biosynthesis in cell suspension cultures of Saussurea involucrata].
PubMed:
[A method based on endogenous fluorescence determination for screening NAMPT inhibitors].
PubMed:
Q&A: The nutrient hunter.
PubMed:
Artichoke, cynarin and cyanidin downregulate the expression of inducible nitric oxide synthase in human coronary smooth muscle cells.
PubMed:
[Development and validation of method for the determination of cynarin, luteolin in plasma].
PubMed:
Development of an automated method for Folin-Ciocalteu total phenolic assay in artichoke extracts.
PubMed:
Inhibition of P-glycoprotein-mediated transport by S-adenosylmethionine and cynarin in multidrug-resistant human uterine sarcoma MES-SA/Dx5 cells.
PubMed:
A new validated HPTLC method for quantitative determination of 1, 5-dicaffeoylquinic acid in Inula crithmoides roots.
PubMed:
Effects of saline stress on mineral composition, phenolic acids and flavonoids in leaves of artichoke and cardoon genotypes grown in floating system.
PubMed:
[Simultaneous determination of 6 active components in Chrysanthemum morifolium by HPLC].
PubMed:
Chip-based protein-protein interaction studied by atomic force microscopy.
PubMed:
Cynarin-rich sunflower (Helianthus annuus) sprouts possess both antiglycative and antioxidant activities.
PubMed:
Polyphenol compounds in artichoke plant tissues and varieties.
PubMed:
Determination of major phenolic compounds in Echinacea spp. raw materials and finished products by high-performance liquid chromatography with ultraviolet detection: single-laboratory validation matrix extension.
PubMed:
1,5-dicaffeoylquinic acid protects primary neurons from amyloid β 1-42-induced apoptosis via PI3K/Akt signaling pathway.
PubMed:
Caffeoylquinic acid derived free radicals identified during antioxidant reactions of bitter tea (Ilex latifolia and Ilex kudincha).
PubMed:
[Phytotherapy with a mixture of dry extracts with hepato-protective effects containing artichoke leaves in the management of functional dyspepsia symptoms].
PubMed:
An improved LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma and its application to a pharmacokinetic study in patients.
PubMed:
Metabolic profile of the bioactive compounds of burdock (Arctium lappa) seeds, roots and leaves.
PubMed:
Phytocontact dermatitis caused by artichoke: an exceptionally rare case.
PubMed:
Blocking effect of an immuno-suppressive agent, cynarin, on CD28 of T-cell receptor.
PubMed:
Effect of two artichoke extracts (36_U and 36_EB) on rat ileum (with respect to bowel syndrome) and the peristaltic threshold.
PubMed:
Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatography-tandem mass spectrometry for pharmacokinetic studies.
PubMed:
Proliferative activity of Echinacea angustifolia root extracts on cancer cells: Interference with doxorubicin cytotoxicity.
PubMed:
Determination of phenolic compounds in fennel by HPLC and HPLC-MS using a monolithic reversed-phase column.
PubMed:
Immuno-suppressive effect of blocking the CD28 signaling pathway in T-cells by an active component of Echinacea found by a novel pharmaceutical screening method.
PubMed:
Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition.
PubMed:
Choleretic effects of yarrow (Achillea millefolium s.l.) in the isolated perfused rat liver.
PubMed:
Pharmacokinetics and metabolism of 1,5-dicaffeoylquinic acid in rats following a single intravenous administration.
PubMed:
Metabolic profile of 1,5-dicaffeoylquinic acid in rats, an in vivo and in vitro study.
PubMed:
Mass spectrometry of 1,3- and 1,5-dicaffeoylquinic acids.
PubMed:
Efficacy of different Cynara scolymus preparations on liver complaints.
PubMed:
A new dilignan from Cynara cardunculus.
PubMed:
Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods.
PubMed:
Evaluation of antioxidant activity of some natural polyphenolic compounds using the Briggs-Rauscher reaction method.
PubMed:
Simultaneous analysis of alkamides and caffeic acid derivatives for the identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Parthenium integrifolium roots.
PubMed:
Phytochemical variation in echinacea from roots and flowerheads of wild and cultivated populations.
PubMed:
Major dicaffeoylquinic acids from Artemisia vulgaris.
PubMed:
Comparison of chemical components and antioxidants capacity of different Echinacea species.
PubMed:
Activity of artichoke leaf extract on reactive oxygen species in human leukocytes.
PubMed:
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.
PubMed:
Echinacoside and caffeoyl conjugates protect collagen from free radical-induced degradation: a potential use of Echinacea extracts in the prevention of skin photodamage.
PubMed:
Radical scavenger activity of different 3',4'-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescence.
PubMed:
Direct characterization of caffeoyl esters with antihyaluronidase activity in crude extracts from Echinacea angustifolia roots by fast atom bombardment tandem mass spectrometry.
PubMed:
TLC and HPLC analysis of Echinacea pallida and E. angustifolia roots.
PubMed:
Hepatoprotective activity of polyphenolic compounds from Cynara scolymus against CCl4 toxicity in isolated rat hepatocytes.
PubMed:
[Phospholipid fractions and free fatty acids in the serum of patients with hypertriglyceridemia treated with 1,5-dicaffeequinine acid].
PubMed:
[Blood coagulation and fibrinolysis systems in patients with hypertriglyceridemia treated with 1,5-dicoffeechinic acid].
PubMed:
[1,5-dicoffeechinic acid in the treatment of hypertriglyceridemia].
PubMed:
[Electroretinographic investigations in subjects in chronic exposure to carbon disulphide: III. Cynarex effect on ERG related to blood lipid pattern (author's transl)].
PubMed:
[Platelet aggregation in workers chronically exposed to carbon disulfide and subjected to prophylactic treatment with Cynarex].
PubMed:
[Determination of cynarin by HPLC in pharmaceutical dosage forms].
PubMed:
[Cynarix. Therapeutic experiences with Cynarix in disorders of fat metabolism in general practice].
PubMed:
[Electroretinographic investigations in subjects with chronic exposure to carbon disulphide: II. Effect of cynarex administration of ERG curves (author's transl)].
PubMed:
Frequently used lipid-lowering drugs having no guaranteed effect.
PubMed:
Effect of 1,5-dicaffeylquinic acid (cynarine) on cholesterol levels in serum and liver of acute ethanol-treated rats.
PubMed:
Effect of 1,5-dicaffeoylquinic acid on ethanol-induced hypertriglyceridemia. Short communication.
PubMed:
[Effect of 1,5-dicafleylquinic acid (cynarine) on hypertriglyceridemia in aged patients].
PubMed:
[Treatment of nephrotic syndromes with cynarine].
PubMed:
[Treatment of nephrotic syndromes with cynarine].
PubMed:
[Isolation and determination of cynarine, chlorogenic acid and caffeic acid with thin-layer chromatography].
PubMed:
[ON POLYPHENOL COMPOUNDS OF THE ARTICHOKE (SYNARA SCOLYMUS L.). II. EXTRACTION OF CYNARINE SALTS].
PubMed:
Therapeutic effects of 1-4-dicaffeil quinic acid (cynarine) administered by oral, rectal, intravenous and intraduodenal way.