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
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Boiling Point: | 215.00 to 217.00 °C. @ 760.00 mm Hg
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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. )
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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.
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
Not determined
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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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 |
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 |
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 |
| 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. |
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