quinic acid 1,5-dicaffeic ester

CAS: 30964-13-7 C25 H24 O12 MW: 516.45668000

Identification

Namecynarine
IUPAC(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
CAS Number30964-13-7
FDA UNII85D81U9JAV
Molecular FormulaC25 H24 O12
Molecular Weight516.45668000
MDL NumberMFCD11112054
Nikkaji NumberJ354.360I

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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for cynarine usage levels up tonot for fragrance use.
Recommendation for cynarine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

artichoke cardoon cynara scolymus fennel plant

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.