protoanemonin
2(5H)-furanone, 5-methylene-
Identification
| Name | protoanemonin |
| IUPAC | 5-methylidenefuran-2-one |
| CAS Number | 108-28-1 |
| EINECS | 203-567-4 |
| FDA UNII | 66FQZ1A5SO |
| Molecular Formula | C5 H4 O2 |
| Molecular Weight | 96.08528000 |
| Nikkaji Number | J10.112E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 219.00 to 220.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.122000 mmHg @ 25.00 °C. (est) |
| Flash Point | 179.00 °F. TCC ( 81.50 °C. ) (est) |
| logP (o/w) | -0.839 (est) |
| Soluble in | alcohol |
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 protoanemonin usage levels up to | not for fragrance use. |
| Recommendation for protoanemonin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2(5H)-
furanone, 5-methylene-
5-
methylene furan-2(5H)-one
5-
methylene-2(5H)-furanone
5-
methylenefuran-2(5H)-one
5-
methylidenefuran-2-one
PubMed:
Differential cytotoxic properties of Helleborus niger L. on tumour and immunocompetent cells.
PubMed:
Comprehensive study of the phenolics and saponins from Helleborus niger L. Leaves and stems by liquid chromatography/tandem mass spectrometry.
PubMed:
New branches in the degradation pathway of monochlorocatechols by Aspergillus nidulans: a metabolomics analysis.
PubMed:
Wild food plants used by the Tibetans of Gongba Valley (Zhouqu county, Gansu, China).
PubMed:
Presentation of three cases with phyto contact dermatitis caused by Ranunculus and Anthemis genera.
PubMed:
Feasibility study of nonclinical safety assessments on homeopathic preparations using the example of protoanemonin in Pulsatilla pratensis L.
PubMed:
Protoanemonin content variation between Clematis spp.: leaf, stem and root.
PubMed:
Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones.
PubMed:
Diastereoselective access to polyoxygenated polycyclic spirolactones through a rhodium-catalyzed [3+2] cycloaddition reaction: experimental and theoretical studies.
PubMed:
Too low to kill: concentration of the secondary metabolite ranunculin in buttercup pollen does not affect bee larval survival.
PubMed:
Protoanemonin: a natural quorum sensing inhibitor that selectively activates iron starvation response.
PubMed:
Consortia modulation of the stress response: proteomic analysis of single strain versus mixed culture.
PubMed:
Novel metal-binding site of Pseudomonas reinekei MT1 trans-dienelactone hydrolase.
PubMed:
Characterization of a gene cluster involved in 4-chlorocatechol degradation by Pseudomonas reinekei MT1.
PubMed:
Irritant contact dermatitis from plants.
PubMed:
Pseudomonas aeruginosa strain RW41 mineralizes 4-chlorobenzenesulfonate, the major polar by-product from DDT manufacturing.
PubMed:
25 years of natural product R&D with New South Wales agriculture.
PubMed:
Phytodermatitis caused by Ceratocephalus falcatus (Ranunculacea).
PubMed:
2-Deoxyribonolactone lesions in X-ray-irradiated DNA: quantitative determination by catalytic 5-methylene-2-furanone release.
PubMed:
The release of 5-methylene-2-furanone from irradiated DNA catalyzed by cationic polyamines and divalent metal cations.
PubMed:
Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species.
PubMed:
New bacterial pathway for 4- and 5-chlorosalicylate degradation via 4-chlorocatechol and maleylacetate in Pseudomonas sp. strain MT1.
PubMed:
[Poisonous and less poisonous plants. 52].
PubMed:
Radiation-activated nuclease activity of o,o'-Diphenyleneiodonium cations (DPI): a reductively initiated chain reaction involving the C1' chemistry.
PubMed:
Formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase.
PubMed:
Polychlorinated biphenyl-degrading microbial communities in soils and sediments.
PubMed:
Mechanism of chloride elimination from 3-chloro- and 2,4-dichloro-cis,cis-muconate: new insight obtained from analysis of muconate cycloisomerase variant CatB-K169A.
PubMed:
Interaction of Sphingomonas and Pseudomonas strains in the degradation of chlorinated dibenzofurans.
PubMed:
Towards elucidation of microbial community metabolic pathways: unravelling the network of carbon sharing in a pollutant-degrading bacterial consortium by immunocapture and isotopic ratio mass spectrometry.
PubMed:
Substrate specificity of and product formation by muconate cycloisomerases: an analysis of wild-type enzymes and engineered variants.
PubMed:
Mechanisms of DNA damage by chromium(V) carcinogens.
PubMed:
Detoxification of protoanemonin by dienelactone hydrolase.
PubMed:
PROTOANEMONIN-INDUCED CYTOTOXIC EFFECTS IN EUGLENA GRACILIS
PubMed:
[More and less toxic plants].
PubMed:
Evidence that Formation of Protoanemonin from Metabolites of 4-Chlorobiphenyl Degradation Negatively Affects the Survival of 4-Chlorobiphenyl-Cometabolizing Microorganisms.
PubMed:
From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway.
PubMed:
DNA cleavage by Cu(II)-desferal: identification of C1'-hydroxylation as the initial event for DNA damage.
PubMed:
Suspected buttercup (Ranunculus bulbosus) toxicosis with secondary photosensitization in a Charolais heifer.
PubMed:
Mechanism of DNA cleavage by cationic manganese porphyrins: hydroxylations at the 1'-carbon and 5'-carbon atoms of deoxyriboses as initial damages.
PubMed:
[Antibacterial activity of vapors of protoanemonine].
PubMed:
In vitro activity of protoanemonin, an antifungal agent.
PubMed:
Ultrastructural alterations in Epidermophyton floccosum and Trichophyton mentagrophytes exposed in vitro to protoanemonin.
PubMed:
Electron microscopy of Microsporum cookei after 'in vitro' treatment with protoanemonin: a combined SEM and TEM study.
PubMed:
[1'-carbon hydroxylation of deoxyribose as the mechanism of cleavage of poly(dA) by manganese porphyrin combined with potassium monopersulfate].
PubMed:
Pharmacologic effects of lactones isolated from Pulsatilla alpina subsp. apiifolia.
PubMed:
Antimicrobial activity of protoanemonin, a lactone from ranunculaceous plants.
PubMed:
Separation and quantitation of protoanemonin in ranunculaceae by normal- and reversed-phase HPLC.
PubMed:
Counter-irritant and other medicinal uses of plants in Ranunculaceae by native peoples in British Columbia and neighbouring areas.
PubMed:
Native American medicinal plants. Anemonin from the horse stimulant Clematis hirsutissima.
PubMed:
Protoanemonin, an antimutagen isolated from plants.
PubMed:
External antirheumatic and antineuralgic herbal remedies in the traditional medicine of north-eastern Italy.
PubMed:
Spectrophotometric determination of protoanemonin, anemonin and ranunculin in Ranunculus sceleratus L.
PubMed:
[Antibiotic activity of protoanemonin in extracts of some lowland species of Ranunculus L].
PubMed:
[On antibacterial, antiviral, antitoxic and cytopathogenic properties of protoanemonin and anemonin].
PubMed:
[Thiol substances and the cytopharmacological effects of protoanemonin on karyokinesis. Experimental research].
PubMed:
[A new synthesis of protoanemonin and of phenylcoumalin. On the knowledge of acetylenecarboxylic acids. XII].
PubMed:
[Preservation of properties of protoanemonin in various solvents].
PubMed:
[Determination of protoanemonin].
PubMed:
Disseminated coccidioidomycosis; treatment with protoanemonin.
PubMed:
Inhibition of Plant Growth by Protoanemonin and Coumarin, and Its Prevention by Bal.
PubMed:
Inhibition of plant growth by protoanemonin and coumarin and its prevention by BAL.
PubMed:
Cytological effects of protoanemonin on the root tip of Zea Mays.
PubMed:
Protoanemonin as a Mitotic Inhibitor.
PubMed:
The inhibition of pyruvic oxidase by protoanemonin.
PubMed:
Range of antibiotic activity of protoanemonin.
PubMed:
A synthesis of protoanemonin; the tautomerism of acetylacrylic acid and of penicillic acid.