| Name: | [(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 |  3D/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, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| 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:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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 | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
|
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.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| 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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