EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

cynarine
quinic acid 1,5-dicaffeic ester

Supplier Sponsors

Name:(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
CAS Number: 30964-13-7Picture of molecule3D/inchi
FDA UNII: 85D81U9JAV
Nikkaji Web:J354.360I
MDL:MFCD11112054
XlogP3-AA:1.50 (est)
Molecular Weight:516.45668000
Formula:C25 H24 O12
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
1,3-Dicaffeoylquinic acid 98%
BOC Sciences
For experimental / research use only.
Cynarin >98%
Odor: characteristic
Use: 1,5-Dicaffeoylquinic acid is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke (Cynara cardunculus). It inhibits taste receptors, making water (and other foods and drinks) seem sweet.
ExtraSynthese
For experimental / research use only.
Cynarine (HPLC) ≥99%
Glentham Life Sciences
Cynarine
Sigma-Aldrich: Sigma
For experimental / research use only.
Cynarine ≥98% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281769
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Chemidplus:0030964137
 
References:
 (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:30964-13-7
Pubchem (cid):5281769
Pubchem (sid):135079016
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):C10445
HMDB (The Human Metabolome Database):HMDB30093
FooDB:FDB001514
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 artichoke
Search Trop Picture
 cardoon
Search Trop Picture
 cynara scolymus
Search Trop Picture
 fennel plant
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent. Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke. Chemically, it is an ester formed from quinic acid and two units of caffeic acid. (Wikipedia)
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