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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 566.20 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 399.00 °F. TCC ( 203.80 °C. ) (est)
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| logP (o/w): | 1.340 (est) |
| Soluble in: |
| | water, 774.6 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for cynaropicrin usage levels up to: | | | not for fragrance use.
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| Recommendation for cynaropicrin flavor usage levels up to: |
| | not for flavor use.
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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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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. |
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