EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Supplier Sponsors

Name:5-methylidenefuran-2-one
CAS Number: 108-28-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-567-4
FDA UNII: 66FQZ1A5SO
Nikkaji Web:J10.112E
XlogP3-AA:0.90 (est)
Molecular Weight:96.08528000
Formula:C5 H4 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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
 water, 1.00E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
4-Methylenebut-2-en-4-olide
 
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
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
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 :66948
National Institute of Allergy and Infectious Diseases:Data
5-methylidenefuran-2-one
Chemidplus:0000108281
 
References:
 5-methylidenefuran-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):66948
Pubchem (sid):135025262
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
UM BBD:Search
KEGG (GenomeNet):C07090
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ranunculus acris
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
a furanone found in ranunculaceae plants; has antifungal & antibiotic properties; ranunculine is hydrolyzed to protoanemonin which dimerizes to anemonin.
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