protoanemonin

2(5H)-furanone, 5-methylene-

CAS: 108-28-1 C5 H4 O2 MW: 96.08528000

Identification

Nameprotoanemonin
IUPAC5-methylidenefuran-2-one
CAS Number108-28-1
EINECS203-567-4
FDA UNII66FQZ1A5SO
Molecular FormulaC5 H4 O2
Molecular Weight96.08528000
Nikkaji NumberJ10.112E

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

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Potential Uses

None Found

Natural Occurrence

ranunculus acris

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.