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
Identification
| Name | cynaropicrin |
| 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 Number | 35730-78-0 |
| FDA UNII | M9233789I9 |
| Molecular Formula | C19 H22 O6 |
| Molecular Weight | 346.37954000 |
| Nikkaji Number | J17.402E |
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 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 cynaropicrin usage levels up to | not for fragrance use. |
| Recommendation for cynaropicrin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.