5,5-dimethyl-2(5H)-furanone
furanone, 5,5-dimethyl-2(5H)-
 
Notes:
Aroma component of hop extract, and of lavender, sagebrush, narcissus and salmon oils
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CAS Number: 20019-64-1Picture of molecule3D/inchi
FDA UNII: 0HJB56V40L
Nikkaji Web: J427.804F
XlogP3-AA: 0.80 (est)
Molecular Weight: 112.12816000
Formula: C6 H8 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 202.00 to  203.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.288000 mmHg @ 25.00 °C. (est)
Flash Point: 163.00 °F. TCC ( 72.90 °C. ) (est)
logP (o/w): 0.247 (est)
Soluble in:
 alcohol
 water, 5.375e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 5,5-dimethyl-2(5H)-furanone usage levels up to:
 not for fragrance use.
 
Recommendation for 5,5-dimethyl-2(5H)-furanone flavor usage levels up to:
 not for flavor use.
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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 : 29909
National Institute of Allergy and Infectious Diseases: Data
 5,5-dimethylfuran-2-one
Chemidplus: 0020019641
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References:
 5,5-dimethylfuran-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 29909
Pubchem (sid): 134994679
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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
HMDB (The Human Metabolome Database): HMDB40260
FooDB: FDB019977
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: 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
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 hop extract
Search Trop  Picture
 lavender
Search Trop  Picture
 narcissus
Search Trop  Picture
 salmon oil
Search  PMC Picture
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Synonyms:
5,5-dimethyl furan-2-one
4,4-dimethyl-2-buten-4-olide
5,5-dimethyl-2-furanone
5,5-dimethylfuran-2-one
5,5-dimethylfuran-2(5H)-one
2(5H)-furanone, 5,5-dimethyl-
 furanone, 5,5-dimethyl-2(5H)-
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Articles:
PubMed: Combustion chemistry and flame structure of furan group biofuels using molecular-beam mass spectrometry and gas chromatography - Part I: Furan.
PubMed: Isolation of a new butenolide from the South China Sea gorgonian coral Subergorgia suberosa.
PubMed: Identifying and quantifying secondhand smoke in source and receptor rooms: logistic regression and chemical mass balance approaches.
PubMed: Protected maleimide building blocks for the decoration of peptides, peptoids, and peptide nucleic acids.
PubMed: Characterization of the key odorants in pan-fried white mushrooms (Agaricus bisporus L.) by means of molecular sensory science: comparison with the raw mushroom tissue.
PubMed: Studies on the key aroma compounds in raw (unheated) and heated Japanese soy sauce.
PubMed: Effect of addition of commercial rosemary extracts on potent odorants in cooked beef.
PubMed: In vitro effects of aldehydes present in tobacco smoke on gene expression in human lung alveolar epithelial cells.
PubMed: Unimolecular decomposition of 2,5-dimethylfuran: a theoretical chemical kinetic study.
PubMed: Characterization of the major odor-active compounds in Thai durian ( Durio zibethinus L. 'Monthong') by aroma extract dilution analysis and headspace gas chromatography-olfactometry.
PubMed: One-pot conversions of lignocellulosic and algal biomass into liquid fuels.
PubMed: Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA).
PubMed: Production of Quorum Sensing Inhibitors in Growing Onion Bulbs Infected with Pseudomonas aeruginosa E (HQ324110).
PubMed: Evaluation of the key aroma compounds in beef and pork vegetable gravies a la chef by stable isotope dilution assays and aroma recombination experiments.
PubMed: Studies on the key aroma compounds in soy milk made from three different soybean cultivars.
PubMed: Thermal generation of 3-amino-4,5-dimethylfuran-2(5H)-one, the postulated precursor of sotolone, from amino acid model systems containing glyoxylic and pyruvic acids.
PubMed: Identification and formation of volatile components responsible for the characteristic aroma of mat rush (igusa).
PubMed: Identification of a sotolon pathway in dry white wines.
PubMed: Characterization of the key aroma compounds in beef and pork vegetable gravies รก la chef by application of the aroma extract dilution analysis.
PubMed: 1-Phenyl-1,2-cyclohexadiene: generation, interception by activated olefins, dimerisation and trimerisation.
PubMed: Decoding the key aroma compounds of a Hungarian-type salami by molecular sensory science approaches.
PubMed: Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests.
PubMed: Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
PubMed: Identification of characteristic aroma components of Thai fried chili paste.
PubMed: Development of accurate classification method based on the analysis of volatile organic compounds from human exhaled air.
PubMed: Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science.
PubMed: Effect of cysteine and cystine addition on sensory profile and potent odorants of extruded potato snacks.
PubMed: Aroma components of acid-hydrolyzed vegetable protein made by partial hydrolysis of rice bran protein.
PubMed: Synthesis and in vivo antihyperglycemic activity of nature-mimicking furanyl-2-pyranones in STZ-S model.
PubMed: Fun with furans.
PubMed: Determination of the preferred conformation of the bicyclic Galerucella pheromone using density functional theory optimization and calculations of chemical shifts.
PubMed: Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla.
PubMed: Identification of potent odorants formed during the preparation of extruded potato snacks.
PubMed: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone levels in fortified Madeira wines: relationship to sugar content.
PubMed: Light effect and reactive oxygen species in the action of ciprofloxacin on Staphylococcus aureus.
PubMed: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone: a key odorant of the typical aroma of oxidative aged Port wine.
PubMed: Influence of human saliva on odorant concentrations. 2. aldehydes, alcohols, 3-alkyl-2-methoxypyrazines, methoxyphenols, and 3-hydroxy-4,5-dimethyl-2(5H)-furanone.
PubMed: Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation.
PubMed: Cycloaddition reactions of dihapto-coordinated furans.
PubMed: Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey.
PubMed: Comparison of key aroma compounds in cooked brown rice varieties based on aroma extract dilution analyses.
PubMed: Sotolone production by hairy root cultures of Trigonella foenum-graecum in airlift with mesh bioreactors.
PubMed: Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies.
PubMed: Photosensitizing activity of thiocolchicoside: photochemical and in vitro phototoxicity studies.
PubMed: Differentiation of the aromas of Merlot and Cabernet Sauvignon wines using sensory and instrumental analysis.
PubMed: Potent odorants of raw Arabica coffee. Their changes during roasting.
PubMed: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (Sotolon) causing an off-flavor: elucidation of its formation pathways during storage of citrus soft drinks.
PubMed: Study of the formation mechanisms of some volatile compounds during the aging of sweet fortified wines.
PubMed: Photoproducts of benzydamine and azapropazone: demonstration of their phototoxicity in vitro.
PubMed: Enhanced proteolysis and changes in membrane-associated calpain following phenylhydrazine insult to human red cells.
PubMed: Afloqualone phototoxicity--photosensitized lipid peroxidative potency and its biological significance.
PubMed: Lipid peroxidative potency of photosensitized thiazide diuretics.
PubMed: Changes of n-hexane neurotoxicity and its urinary metabolites by long-term co-exposure with MEK or toluene.
PubMed: A study on biological monitoring of n-hexane exposure.
PubMed: Changes of n-hexane metabolites in urine of rats exposed to various concentrations of n-hexane and to its mixture with toluene or MEK.
PubMed: Photosensitization by drugs: photolysis of some chlorine-containing drugs.
PubMed: Singlet oxygen as a mediator in the hematoporphyrin-catalyzed photooxidation of NADPH to NADP+ in deuterium oxide.
PubMed: Steam volatile aroma constituents of roasted coffee: neutral fraction.
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