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

CAS: 35730-78-0 C19 H22 O6 MW: 346.37954000

Identification

Namecynaropicrin
IUPAC[(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
CAS Number35730-78-0
FDA UNIIM9233789I9
Molecular FormulaC19 H22 O6
Molecular Weight346.37954000
Nikkaji NumberJ17.402E

Regulatory

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)

No sensory data available

Safety Information

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 cynaropicrin usage levels up tonot for fragrance use.
Recommendation for cynaropicrin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

artichoke cardoon cynara scolymus

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 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.