Category:flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | white to brown crystals (est) |
Assay: | 97.00 to 100.00
|
Food Chemicals Codex Listed: | No |
Melting Point: | 126.00 to 133.00 °C. @ 760.00 mm Hg
|
Boiling Point: | 215.00 to 217.00 °C. @ 760.00 mm Hg
|
Acid Value: | 4.00 max. KOH/g
|
Vapor Pressure: | 0.027000 mmHg @ 25.00 °C. (est) |
Flash Point: | 207.00 °F. TCC ( 97.22 °C. )
|
logP (o/w): | -0.611 (est) |
Shelf Life: | 12.00 month(s) or longer if stored properly. |
Storage: | store in cool, dry place in tightly sealed containers, protected from heat and light. |
Soluble in: |
| dipropylene glycol | | propylene glycol | | water, 4.739e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
Cosmetic Information:
Suppliers:
Safety Information:
Preferred SDS: View |
European information : |
Most important hazard(s): | Xn - Harmful. |
R 20/22 - Harmful by inhalation and if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 22 - Do not breath dust. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
|
|
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: | flavor and fragrance agents |
RIFM Fragrance Material Safety Assessment: Search |
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
Recommendation for toffee furanone usage levels up to: | | 0.1000 % in the fragrance concentrate.
|
|
Maximised Survey-derived Daily Intakes (MSDI-EU): | 5.60 (μg/capita/day) |
Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.07 (μg/capita/day) |
Structure Class: | II |
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). |
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library |
publication number: 12 |
Click here to view publication 12 |
| average usual ppm | average maximum ppm |
baked goods: | - | - |
beverages(nonalcoholic): | - | - |
beverages(alcoholic): | - | - |
breakfast cereal: | - | - |
cheese: | - | - |
chewing gum: | - | - |
condiments / relishes: | - | 20.00000 |
confectionery froastings: | - | - |
egg products: | - | - |
fats / oils: | - | 20.00000 |
fish products: | - | 35.00000 |
frozen dairy: | - | - |
fruit ices: | - | - |
gelatins / puddings: | - | 10.00000 |
granulated sugar: | - | - |
gravies: | - | 10.00000 |
hard candy: | - | - |
imitation dairy: | - | - |
instant coffee / tea: | - | - |
jams / jellies: | - | - |
meat products: | - | 35.00000 |
milk products: | - | - |
nut products: | - | 20.00000 |
other grains: | - | - |
poultry: | - | 35.00000 |
processed fruits: | - | - |
processed vegetables: | - | - |
reconstituted vegetables: | - | - |
seasonings / flavors: | - | 1.00000 |
snack foods: | - | 35.00000 |
soft candy: | - | - |
soups: | - | 10.00000 |
sugar substitutes: | - | - |
sweet sauces: | - | 20.00000 |
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
|
European Food Safety Authority (EFSA) reference(s):
|
Flavouring Group Evaluation 220: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 220, Revision 1 (FGE.220Rev1): alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 99 (FGE.99): Consideration of furanone derivatives evaluated by the JECFA (63rd, 65th and 69th meetings) View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 220, Revision 2 (FGE.220Rev1): a,ß-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 220 Revision 3 (FGE.220Rev3): Consideration of genotoxic potential for a,ß-unsaturated 3(2H)-Furanones from subgroup 4.4 of FGE.19 View page or View pdf
|
Scientific Opinion on Flavouring Group Evaluation 99 Revision 1 (FGE.99Rev1): Consideration of furanone derivatives evaluated by the JECFA (63rd, 65th and 69th meetings) View page or View pdf
|
EPI System: View |
Chemical Carcinogenesis Research Information System:Search |
AIDS Citations:Search |
Cancer Citations:Search |
Toxicology Citations:Search |
EPA Substance Registry Services (TSCA):19322-27-1 |
EPA ACToR:Toxicology Data |
EPA Substance Registry Services (SRS):Registry |
Laboratory Chemical Safety Summary :4564493 |
National Institute of Allergy and Infectious Diseases:Data |
WGK Germany:3 |
4-hydroxy-5-methylfuran-3-one |
Chemidplus:0019322271 |
References:
Other Information:
Potential Blenders and core components note
For Odor |
acidic |
cyclohexyl acetic acid FL/FR |
balsamic |
2- acetyl furan FL/FR |
benzyl salicylate FL/FR |
fir balsam absolute FR |
3- phenyl propyl alcohol FL/FR |
berry |
raspberry ketone FL/FR |
bready |
coffee furanone FL/FR |
buttery |
acetoin FL/FR |
acetyl propionyl FL/FR |
3,4- hexane dione FL/FR |
caramellic |
2-iso butyl-3-methyl pyrazine FL/FR |
2-oxo butyric acid FL/FR |
caramel pentadione FL/FR |
coffee dione FL/FR |
cyclotene FL/FR |
cyclotene hydrate FL/FR |
diethyl malate FL/FR |
alpha,alpha- dimethyl anisyl acetone FL/FR |
ethyl 2-hydroxy-2-methyl butyrate FL/FR |
ethyl cyclopentenolone FL/FR |
ethyl maltol FL/FR |
5- ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one FL/FR |
fenugreek absolute FL/FR |
geranyl crotonate FR |
immortelle absolute FL/FR |
levulinic acid FL/FR |
maltol FL/FR |
maltyl isobutyrate FL/FR |
maltyl propionate FL/FR |
maple furanone FL/FR |
menthone lactone FL/FR |
mesitene lactone FR |
5- methyl furfural FL/FR |
iso propenyl pyrazine FL/FR |
rosefuran FL/FR |
shoyu furanone FL/FR |
strawberry furanone FL/FR |
strawberry furanone solution FL/FR |
chocolate |
2,4,5- trimethyl thiazole FL/FR |
citrus |
blood orange oil italy FL/FR |
coconut |
gamma- heptalactone FL/FR |
gamma- octalactone FL/FR |
coumarinic |
tonka bean resinoid FR |
creamy |
gamma- butyrolactone FL/FR |
ethereal |
ethyl 4-pentenoate FL/FR |
ethyl pyruvate FL/FR |
iso valeraldehyde propylene glycol acetal FL/FR |
fermented |
ethyl (E)-2-crotonate FL/FR |
floral |
beta- damascenone FL/FR |
ethyl phenyl acetate FL/FR |
floral pyranol FR |
heliotropin FL/FR |
heliotropyl acetone FL/FR |
alpha- hexyl cinnamaldehyde FL/FR |
methyl dihydrojasmonate FL/FR |
mimosa absolute france FL/FR |
nerolidol FL/FR |
ocean propanal FL/FR |
fruity |
beta- damascone FL/FR |
gamma- decalactone FL/FR |
(E)- ethyl tiglate FL/FR |
osmanthus flower absolute FL/FR |
tetrahydrofurfuryl acetate FL/FR |
gamma- undecalactone (aldehyde C-14 (so-called)) FL/FR |
green |
iso amyl 3-(2-furan) propionate FL/FR |
methyl octine carbonate FL/FR |
(E,Z)-2,6- nonadien-1-ol FL/FR |
violet leaf absolute FL/FR |
hay |
beeswax absolute FL/FR |
herbal |
butyl levulinate FL/FR |
honey |
methyl phenyl acetate FL/FR |
melon |
melon heptenal FL/FR |
(Z)-6- nonenal FL/FR |
mossy |
veramoss (IFF) FR |
musty |
3- acetyl-2,5-dimethyl furan FL/FR |
nutty |
2- acetyl-3,5(or 6)-dimethyl pyrazine FL/FR |
2,3- dimethyl pyrazine FL/FR |
nutty cyclohexenone FL/FR |
phenolic |
4- methyl-2,6-dimethoxyphenol FL/FR |
popcorn |
2- acetyl pyrazine FL/FR |
2- acetyl pyridine FL/FR |
powdery |
para- anisyl acetate FL/FR |
spicy |
cassia bark oil china FL/FR |
black currant bud absolute FL/FR |
iso eugenyl acetate FL/FR |
(E)- tiglic acid FL/FR |
sugar |
cotton candy fragrance FR |
sweet |
vanilla oleoresin bali FL/FR |
tonka |
tonka bean absolute FR |
vanilla |
ethyl vanillin FL/FR |
vanillin FL/FR |
vanillyl isobutyrate FL/FR |
vegetable |
tetrahydrofurfuryl alcohol FL/FR |
woody |
santall FR |
For Flavor |
No flavor group found for these |
2- acetyl-3,4,5,6-tetrahydropyridine FL |
allyl 2-furoate FL |
benzyl disulfide FL |
diethyl malate FL/FR |
2,5- diethyl tetrahydrofuran FL |
alpha,alpha- dimethyl anisyl acetone FL/FR |
ethyl 2-hydroxy-2-methyl butyrate FL/FR |
ethyl 2,5-dimethyl-3-oxo-4(2H)-furyl carbonate FL |
ethyl 4-pentenoate FL/FR |
5- ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one FL/FR |
furfuryl acetone FL |
menthone lactone FL/FR |
rosefuran FL/FR |
|
iso amyl 3-(2-furan) propionate FL/FR |
beta- damascone FL/FR |
acidic |
acidic |
levulinic acid FL/FR |
dextro,laevo- tartaric acid FL |
apple |
(E,Z)-2,6- nonadien-1-ol FL/FR |
balsamic |
benzyl salicylate FL/FR |
berry |
heliotropyl acetone FL/FR |
raspberry ketone FL/FR |
bready |
mango furanone FL |
brown |
beeswax absolute FL/FR |
2-oxo butyric acid FL/FR |
5- methyl furfural FL/FR |
tetrahydrofurfuryl acetate FL/FR |
(E)- tiglic acid FL/FR |
burnt |
furfuryl alcohol FL |
iso propenyl pyrazine FL/FR |
buttery |
diacetyl FL |
3,4- hexane dione FL/FR |
caramellic |
caramel dione FL |
caramel furanone FL |
caramel pentadione FL/FR |
cyclotene FL/FR |
cyclotene hydrate FL/FR |
ethyl maltol FL/FR |
5- ethyl-3,4,5,6-tetramethyl cyclohexen-2-one FL |
fenugreek absolute FL/FR |
maltol FL/FR |
maltyl propionate FL/FR |
maple furanone FL/FR |
3- methyl butyl 2-furyl butyrate FL |
shoyu furanone FL/FR |
strawberry furanone FL/FR |
strawberry furanone solution FL/FR |
cherry |
heliotropin FL/FR |
citrus |
blood orange oil italy FL/FR |
coffee |
coffee dione FL/FR |
2- thiophene thiol FL |
corn |
2- acetyl pyridine FL/FR |
2- acetyl-2-thiazoline FL |
creamy |
acetoin FL/FR |
gamma- undecalactone (aldehyde C-14 (so-called)) FL/FR |
dairy |
creme brulle coffee flavor FL |
fatty |
2,4- undecadienal FL |
(E,E)-2,4- undecadienal FL |
floral |
methyl dihydrojasmonate FL/FR |
methyl phenyl acetate FL/FR |
ocean propanal FL/FR |
fruity |
para- anisyl acetate FL/FR |
gamma- decalactone FL/FR |
(E)- ethyl tiglate FL/FR |
furfuryl valerate FL |
osmanthus flower absolute FL/FR |
2- pentanoyl furan FL |
iso valeraldehyde propylene glycol acetal FL/FR |
green |
2-iso butyl-3-methyl pyrazine FL/FR |
immortelle absolute FL/FR |
melon heptenal FL/FR |
methyl octine carbonate FL/FR |
nerolidol FL/FR |
(Z)-6- nonenal FL/FR |
violet leaf absolute FL/FR |
herbal |
butyl levulinate FL/FR |
5- hydroxymethyl furfural FL |
honey |
ethyl phenyl acetate FL/FR |
jammy |
ethyl cyclopentenolone FL/FR |
maltyl isobutyrate FL/FR |
lactonic |
gamma- heptalactone FL/FR |
gamma- octalactone FL/FR |
meaty |
2- mercaptomethyl pyrazine FL |
milky |
gamma- butyrolactone FL/FR |
musty |
ethyl (E)-2-crotonate FL/FR |
nutty |
2- acetyl furan FL/FR |
3- acetyl-2,5-dimethyl furan FL/FR |
2- acetyl-3,5(or 6)-dimethyl pyrazine FL/FR |
3,5(6)- cocoa pyrazine FL |
coffee furanone FL/FR |
2,3- dimethyl pyrazine FL/FR |
nutty cyclohexenone FL/FR |
peanut oxazole FL |
tetrahydrofurfuryl alcohol FL/FR |
2,4,5- trimethyl thiazole FL/FR |
phenolic |
4- methyl-2,6-dimethoxyphenol FL/FR |
roasted |
2- acetyl pyrazine FL/FR |
rummy |
ethyl pyruvate FL/FR |
spicy |
cassia bark oil china FL/FR |
black currant bud absolute FL/FR |
iso eugenyl acetate FL/FR |
3- phenyl propyl alcohol FL/FR |
sweet |
cyclohexyl acetic acid FL/FR |
dextro- sorbitol FL |
vanilla oleoresin bali FL/FR |
toasted |
acetyl propionyl FL/FR |
vanilla |
ethyl vanillin FL/FR |
vanillin FL/FR |
vanillyl isobutyrate FL/FR |
waxy |
furfuryl octanoate FL |
alpha- hexyl cinnamaldehyde FL/FR |
mimosa absolute france FL/FR |
woody |
beta- damascenone FL/FR |
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| chicory furaneol | | chicory furanone | | chicory furanone 5% in PG natural | | chicory furanone 5% in PG synthetic | | chicory furanone synthetic | | furan-3(2H)-one, 4-hydroxy-5-methyl- | nor | furaneol | 3(2H)- | furanone, 4-hydroxy-5-methyl- | 4- | hydroxy-5-methyl furan-3-one | 4- | hydroxy-5-methyl furan-3(2H)-one | 4- | hydroxy-5-methyl-2-hydrofuran-3-one | 4- | hydroxy-5-methyl-2,3-dihydrofuran-3-one | 4- | hydroxy-5-methyl-3-(2H)-furanone | 4- | hydroxy-5-methyl-3-(2H)furanone | 4- | hydroxy-5-methyl-3-furanone | 4- | hydroxy-5-methyl-3(2H)-furanone | 4- | hydroxy-5-methyl-3(2H)furanone | 4- | hydroxy-5-methylfuran-3-one | 4- | hydroxy-5-methylfuran-3(2H)-one | 4- | hyroxy-5-methyl-3-furanone | | methyl furaneol | 5- | methyl-4-hydroxy-2,3-dihydrofuran-3-one | 5- | methyl-4-hydroxy-3,2H-furanone | 5- | methyl-4-hydroxy-3(2H)-furanone |
Articles:
PubMed:Comparative volatile profiles in soy sauce according to inoculated microorganisms. |
PubMed:An in vitro study reveals nutraceutical properties of Ananas comosus (L.) Merr. var. Mauritius fruit residue beneficial to diabetes. |
PubMed:Key aroma compounds in roasted in-shell peanuts. |
PubMed:Natural 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®). |
PubMed:The periodontopathogenic bacterium Eikenella corrodens produces an autoinducer-2-inactivating enzyme. |
PubMed:Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone. |
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:D-Galacturonic acid as a highly reactive compound in nonenzymatic browning. 1. Formation of browning active degradation products. |
PubMed:An efficient method for the determination of furan derivatives in apple cider and wine by solid phase extraction and high performance liquid chromatography--diode array detector. |
PubMed:Volatile profiling of high quality hazelnuts (Corylus avellana L.): chemical indices of roasting. |
PubMed:DNA damage by genotoxic hydroxyhalofuranones: an in silico approach to MX. |
PubMed:Furanone derivatives from terrestrial Streptomyces spp. |
PubMed:Characterization of the key odorants in raw Italian hazelnuts ( Corylus avellana L. var. Tonda Romana) and roasted hazelnut paste by means of molecular sensory science. |
PubMed:Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA). |
PubMed:An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements. |
PubMed:Main odorants in Jura flor-sherry wines. Relative contributions of sotolon, abhexon, and theaspirane-derived compounds. |
PubMed:Evaluation of volatiles from two subtropical strawberry cultivars using GC-olfactometry, GC-MS odor activity values, and sensory analysis. |
PubMed:The volatile compounds in lamb fat are affected by the time of grazing. |
PubMed:Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds. |
PubMed:Convenient synthesis of 3,4-dichloro-5-hydroxy-2(5H)-furanone glycoconjugates. |
PubMed:Kinetics of the reactions of OH radicals with 2- and 3-methylfuran, 2,3- and 2,5-dimethylfuran, and E- and Z-3-hexene-2,5-dione, and products of OH + 2,5-dimethylfuran. |
PubMed:Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds. |
PubMed:Identification and formation of volatile components responsible for the characteristic aroma of mat rush (igusa). |
PubMed:Identification of novel aroma-active thiols in pan-roasted white sesame seeds. |
PubMed:Genome shuffling of Zygosaccharomyces rouxii to accelerate and enhance the flavour formation of soy sauce. |
PubMed:Stereochemical study of a novel tautomeric furanone, homofuraneol. |
PubMed:Development of a method based on on-line reversed phase liquid chromatography and gas chromatography coupled by means of an adsorption-desorption interface for the analysis of selected chiral volatile compounds in methyl jasmonate treated strawberries. |
PubMed:Identification of dihydromaltol (2,3-dihydro-5-hydroxy-6-methyl-4H-pyran-4-one) in Ryazhenka Kefir and comparative sensory impact assessment of related cycloenolones. |
PubMed:Improved derivatization technique for gas chromatography-mass spectrometry determination of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in drinking water. |
PubMed:Cytotoxic and HIF-1alpha inhibitory compounds from Crossosoma bigelovii. |
PubMed:Decoding the key aroma compounds of a Hungarian-type salami by molecular sensory science approaches. |
PubMed:Absorption of 3(2H)-furanones by human intestinal epithelial Caco-2 cells. |
PubMed:Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests. |
PubMed:Norfuraneol dephosphorylates eNOS at threonine 495 and enhances eNOS activity in human endothelial cells. |
PubMed:General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid. |
PubMed:Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis. |
PubMed:Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis. |
PubMed:Effects of water-soluble natural antioxidants on photosensitized oxidation of conjugated linoleic acid in an oil-in-water emulsion system. |
PubMed:A dual mechanism of 4-hydroxy-5-methyl-3[2H]-furanone inhibiting cellular melanogenesis. |
PubMed:Identification of characteristic aroma components of Thai fried chili paste. |
PubMed:The aroma side of the Maillard reaction. |
PubMed:Functional characterization of enone oxidoreductases from strawberry and tomato fruit. |
PubMed:Effects of the amino-carbonyl reaction of ribose and glycine on the formation of the 2(or 5)-ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-furanone aroma component specific to miso by halo-tolerant yeast. |
PubMed:Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science. |
PubMed:Identification of sulfur volatiles in canned orange juices lacking orange flavor. |
PubMed:Effect of cysteine and cystine addition on sensory profile and potent odorants of extruded potato snacks. |
PubMed:Prooxidant action of furanone compounds: implication of reactive oxygen species in the metal-dependent strand breaks and the formation of 8-hydroxy-2'-deoxyguanosine in DNA. |
PubMed:The formation mechanism by yeast of 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone in Miso. |
PubMed:New constituents related to 3-methyl-2,4-nonanedione identified in green tea. |
PubMed:Two 2[5H]-furanones as possible signaling molecules in Lactobacillus helveticus. |
PubMed:FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase. |
PubMed:Functional effects of Japanese style fermented soy sauce (shoyu) and its components. |
PubMed:4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) production in simple media by lactic acid bacterium, Lactococcus lactis subsp. cremoris IFO 3427. |
PubMed:Characterization of dried whey protein concentrate and isolate flavor. |
PubMed:Altered expression of connexin43 in the inhibition of gap junctional intercellular communication by chlorohydroxyfuranones in WB-F344 rat liver epithelial cells. |
PubMed:Identification of potent odorants formed during the preparation of extruded potato snacks. |
PubMed:Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation. |
PubMed:Alleviation of aflatoxin B1-induced oxidative stress in HepG2 cells by volatile extract from Allii Fistulosi Bulbus. |
PubMed:Concurrent phenomena contributing to the formation of the aroma of wine during aging in oak wood: an analytical study. |
PubMed:Identification of potent odorants in different cultivars of snake fruit [Salacca zalacca (Gaert.) Voss] using gas chromatography-olfactometry. |
PubMed:Quorum sensing in Clostridium difficile: analysis of a luxS-type signalling system. |
PubMed:Cytotoxicity of 3,4-dihalogenated 2(5H)-furanones. |
PubMed:Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington. |
PubMed:Potent inhibition of gap junctional intercellular communication by 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in BALB/c 3T3 cells. |
PubMed:Bacterial and mammalian-cell genotoxicity of mixtures of chlorohydroxyfuranones, by-products of water chlorination. |
PubMed:Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines. |
PubMed:Evaluation of multiwavelength culture fluorescence for monitoring the aroma compound 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) production. |
PubMed:Effects of chlorohydroxyfuranones on 3-methylcholanthrene-induced neoplastic transformation in the two-stage transformation assay in C3H 10T1/2 cells. |
PubMed:Alternative pathway for the formation of 4,5-dihydroxy-2,3-pentanedione, the proposed precursor of 4-hydroxy-5-methyl-3(2H)-furanone as well as autoinducer-2, and its detection as natural constituent of tomato fruit. |
PubMed:Quantitative determination of sotolon, maltol and free furaneol in wine by solid-phase extraction and gas chromatography-ion-trap mass spectrometry. |
PubMed:Formation of 4-hydroxy-2,5-dimethyl-3[2H]-furanone by Zygosaccharomyces rouxii: identification of an intermediate. |
PubMed:Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. laciniatus L.) blackberries. |
PubMed:Sesquiterpenoids from Artemisia gilvescens and an anti-MRSA compound. |
PubMed:Formation of aroma compounds from ribose and cysteine during the Maillard reaction. |
PubMed:Potential of gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) in flavor research. |
PubMed:Investigation of the change in the flavor of a coffee drink during heat processing. |
PubMed:Maillard reaction products modulating the growth of human tumor cells in vitro. |
PubMed:Volatile constituents of glutathione--ribose model system and its antioxidant activity. |
PubMed:Formation of 5-methyl-4-hydroxy-3[2H]-furanone in cytosolic extracts obtained from Zygosaccharomyces rouxii. |
PubMed:Changes in the volatile compounds and in the chemical and physical properties of snake fruit (Salacca edulis Reinw) Cv. Pondoh during maturation. |
PubMed:Identification of potent odorants in Chinese jasmine green tea scented with flowers of Jasminum sambac. |
PubMed:Characterization of Trp(+) reversions in Escherichia coli strain WP2uvrA. |
PubMed:Formation of sulfur aroma compounds in reaction mixtures containing cysteine and three different forms of ribose. |
PubMed:Aroma biosynthesis in strawberry: s-adenosylmethionine:furaneol o-methyltransferase activity in ripening fruits. |
PubMed:Maillard reaction of D-glucose: identification of a colored product with conjugated pyrrole and furanone rings. |
PubMed:LuxS: its role in central metabolism and the in vitro synthesis of 4-hydroxy-5-methyl-3(2H)-furanone. |
PubMed:Volatile flavor components of stored nonfat dry milk. |
PubMed:Comparable DNA and chromosome damage in Chinese hamster ovary cells by chlorohydroxyfuranones. |
PubMed:Application of sec-butanol to the derivatization of hydroxyfuranones. |
PubMed:Stability of thiols in an aqueous process flavoring. |
PubMed:Halogenated 2,5-pyrrolidinediones: synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations. |
PubMed:Identification of new heterocyclic nitrogen compounds from glucose-lysine and xylose-lysine maillard model systems. |
PubMed:Heterocyclic volatiles formed by heating cysteine or hydrogen sulfide with 4-hydroxy-5-methyl-3(2H)-furanone at pH 6.5. |
PubMed:Influence of pyrolytic and aqueous-phase reactions on the mechanism of formation of Maillard products. |
PubMed:A comparison of mutation spectra detected by the Escherichia coli lac(+) reversion assay and the Salmonella typhimurium his(+) reversion assay. |
PubMed:Inhibition of iron ion-induced oxidative damage of erythrocyte membranes and low density lipoprotein by a Maillard product, 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF). |
PubMed:Mutation spectra of the drinking water mutagen 3-chloro-4-methyl-5-hydroxy-2(5H)-furanone (MCF) in Salmonella TA100 and TA104: comparison to MX. |
PubMed:Effect of food reductones on the generation of the pyrazine cation radical and on the formation of the mutagens in the reaction of glucose, glycine and creatinine. |
PubMed:Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase. |
PubMed:Biomolecular-chemical screening: a novel screening approach for the discovery of biologically active secondary metabolites. III. New DNA-binding metabolites. |
PubMed:Reinvestigation of the reaction between 2-furancarboxaldehyde and 4-hydroxy-5-methyl-3(2H)-furanone. |
PubMed:Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)-furanone and cysteine or hydrogen sulfide at pH 4.5. |
PubMed:Biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and derivatives in in vitro grown strawberries. |
PubMed:Analysis of furanone, pyranone, and new heterocyclic colored compounds from sugar-glycine model Maillard systems. |
PubMed:Genotoxic activity of chlorohydroxyfuranones in the microscale micronucleus test on mouse lymphoma cells and the unscheduled DNA synthesis assay in rat hepatocytes. |
PubMed:The naturally occurring furanones: formation and function from pheromone to food. |
PubMed:Effect of media constituents on the formation by halophilic yeast of the 2 (or 5)-ethyl-5 (or 2)-methyl-4-hydroxy-3 (2H)-furanone aroma component specific to miso. |
PubMed:Promoting effects of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone on rat glandular stomach carcinogenesis initiated with N-methyl-N'-nitro-N-nitrosoguanidine. |
PubMed:Effects of protocatechuic acid, S-methylmethanethiosulfonate or 5-hydroxy-4-(2-phenyl-(E)ethenyl)-2(5H)-furanone(KYN-54) on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced pulmonary carcinogenesis in mice. |
PubMed:Synthesis of 4-hydroxy-3(2H)-furanone acyl derivatives and their anti-cataract effect on spontaneous cataract rats (ICR/f). |
PubMed:Antioxidative activities of 4-hydroxy-3(2H)-furanones and their anti-cataract effect on spontaneous cataract rat (ICR/f). |
PubMed:Absorption and induction of micronucleated peripheral reticulocytes in mice after oral administration of fragrant hydroxyfuranones generated in the Maillard reaction. |
PubMed:Identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) with DNA breaking activity in soy sauce. |
PubMed:Chemometric applications of thermally produced compounds as time-temperature integrators in aseptic processing of particulate foods. |
PubMed:Identification of adenine adducts formed in reaction of calf thymus DNA with mutagenic chlorohydroxyfuranones found in drinking water. |
PubMed:Bromine-, chlorine-, and mixed halogen-substituted 4-methyl-2(5H)-furanones: synthesis and mutagenic effects of halogen and hydroxyl group replacements. |
PubMed:Regressive effects of various chemopreventive agents on azoxymethane-induced aberrant crypt foci in the rat colon. |
PubMed:Detection of genotoxicity of polluted sea water using shellfish and the alkaline single-cell gel electrophoresis (SCE) assay: a preliminary study. |
PubMed:Inhibition of benzo[a]pyrene-induced mouse forestomach neoplasia and reduction of H2O2 concentration in human polymorphonuclear leucocytes by flavour components of Japanese-style fermented soy sauce. |
PubMed:Mucochloric acid action on phi X174 DNA: a comparison to other chlorine-substituted 2(5H)-furanones. |
PubMed:Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity. |
PubMed:Synthesis of Highly Functionalized gamma-Butyrolactones from Activated Carbonyl Compounds and Dimethyl Acetylenedicarboxylate. |
PubMed:Identification of adducts formed in reaction of adenosine with 3-chloro-4-methyl-5-hydroxy-2(5H)-furanone, a bacterial mutagen present in chloride disinfected drinking water. |
PubMed:DNA breaking activity and mutagenicity of soy sauce: characterization of the active components and identification of 4-hydroxy-5-methyl-3(2H)-furanone. |
PubMed:DNA strand breaks induced through active oxygen radicals by fragrant component 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone in Maillard reaction of hexose/amino acid. |
PubMed:The determination of strong mutagen MX [3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone] in drinking water in China. |
PubMed:Male sex pheromone of cockroachEurycotis floridana (walker) (Blattidae, Polyzosteriinae): Role and composition of tergites 2 and 8 secretions. |
PubMed:Biodegradation of 4-methyl-5-nitrocatechol by Pseudomonas sp. strain DNT. |
PubMed:Inhibition of benzo[a]pyrene-induced mouse forestomach neoplasia by a principal flavor component of Japanese-style fermented soy sauce. |
PubMed:Structure-activity relationships of bacterial mutagens related to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone: an emphasis on the effect of stepwise removal of chlorine from the dichloromethyl group. |
PubMed:Salmonella typhimurium (TA100) mutagenicity of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and its open- and closed-ring analogs. |
PubMed:Genotoxicity of drinking waters. |
PubMed:Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and of its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. |
|