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

cynaropicrin
2-propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester

Supplier Sponsors

CAS Number: 35730-78-0Picture of molecule3D/inchi
FDA UNII:M9233789I9
Nikkaji Web:J17.402E
XlogP3-AA:0.60 (est)
Molecular Weight:346.37954000
Formula:C19 H22 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome 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: 566.20 °C. @ 760.00 mm Hg (est)
Flash Point: 399.00 °F. TCC ( 203.80 °C. ) (est)
logP (o/w): 1.340 (est)
Soluble in:
 water, 774.6 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.
Cynaropicrin 96%
BOC Sciences
For experimental / research use only.
Cynaropikrin > 98%
Odor: characteristic
Use: Cynaropikrin, a polyphenolic compound, is a sesquiterpene lactone in C. scolymus. Cynaropikrin is the bitter principle in artichoke and is, therefore, an important compound in the chemical profiling of the plant. Cynara scolymus L. (Asteraceae),
ExtraSynthese
For experimental / research use only.
Cynaropicrin (HPLC) ≥97.5%
Glentham Life Sciences
Cynaropicrin
 
Safety Information:
 
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 cynaropicrin usage levels up to:
 not for fragrance use.
 
Recommendation for cynaropicrin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :119093
National Institute of Allergy and Infectious Diseases:Data
[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Chemidplus:0035730780
 
References:
 [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):119093
Pubchem (sid):135074151
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09385
HMDB (The Human Metabolome Database):HMDB36423
FooDB:FDB015308
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
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
 
Synonyms:
[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
2-propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester
 

Articles:

PubMed:Phytotoxicity of cardoon (Cynara cardunculus) allelochemicals on standard target species and weeds.
PubMed:Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway.
PubMed:Structure-activity relationship study of sesquiterpene lactones and their semi-synthetic amino derivatives as potential antitrypanosomal products.
PubMed:Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives.
PubMed:Mild oxidative stress induces S-glutathionylation of STAT3 and enhances chemosensitivity of tumoural cells to chemotherapeutic drugs.
PubMed:Cynaropicrin targets the trypanothione redox system in Trypanosoma brucei.
PubMed:Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivo.
PubMed:Antiprotozoal screening of 60 South African plants, and the identification of the antitrypanosomal germacranolides schkuhrin I and II.
PubMed:Lipophilic extracts of Cynara cardunculus L. var. altilis (DC): a source of valuable bioactive terpenic compounds.
PubMed:Cynaropicrin from Cynara scolymus L. suppresses photoaging of skin by inhibiting the transcription activity of nuclear factor-kappa B.
PubMed:Genetic mapping and characterization of the globe artichoke (+)-germacrene A synthase gene, encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone cynaropicrin.
PubMed:Cynaropicrin: the first plant natural product with in vivo activity against Trypanosoma brucei.
PubMed:Quantification of cynaropicrin in artichoke leaf extracts by ¹H NMR spectroscopy.
PubMed:Effects of artichoke leaf extract on acute gastric mucosal injury in rats.
PubMed:Supercritical fluid extraction of cynaropicrin and 20-hydroxyecdysone from Leuzea carthamoides DC.
PubMed:The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme.
PubMed:Sesquiterpene lactones from Saussurea alata.
PubMed:Saussurea costus: botanical, chemical and pharmacological review of an ayurvedic medicinal plant.
PubMed:[Studies on chemical constituents of Acroptilon repens].
PubMed:Choleretic effects of the Mongolian medicinal plant Saussurea amara in the isolated perfused rat liver.
PubMed:Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
PubMed:Cytotoxic sesquiterpene lactones from Saussurea calcicola.
PubMed:Antispasmodic activity of fractions and cynaropicrin from Cynara scolymus on guinea-pig ileum.
PubMed:Cytotoxic and pro-apoptotic activities of cynaropicrin, a sesquiterpene lactone, on the viability of leukocyte cancer cell lines.
PubMed:Trypanocidal and antimicrobial activities of Moquinia kingii.
PubMed:Cynaropicrin, a sesquiterpene lactone, as a new strong regulator of CD29 and CD98 functions.
PubMed:Cytotoxic effects of sesquiterpene lactones from the flowers of Hemisteptia lyrata B.
PubMed:Cytotoxic sesquiterpene lactones from Centaurothamnus maximus and Vicoa pentanema.
PubMed:Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action.
PubMed:Savinin, a lignan from Pterocarpus santalinus inhibits tumor necrosis factor-alpha production and T cell proliferation.
PubMed:In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa.
PubMed:Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-alpha production in murine macrophage-like cells.
PubMed:Constituents of the Egyptian Centaurea scoparia; Part II. Guaianolides of the Aerial Parts.
PubMed:Toxic inhibition of smooth muscle contractility by plant-derived sesquiterpenes caused by their chemically reactive alpha-methylenebutyrolactone functions.
PubMed:Toxic effects of solstitialin A 13-acetate and cynaropicrin from Centaurea solstitialis L. (Asteraceae) in cell cultures of foetal rat brain.
PubMed:New cytotoxic guaianolides and derivatives from Grosheimia macrocephala.
 
Notes:
Constit. of Cynara scolymus (artichoke)
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