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

toffee furanone
4-hydroxy-5-methyl-3(2H)-furanone

Sponsors

Name:4-hydroxy-5-methylfuran-3-one
CAS Number: 19322-27-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-961-0
FDA UNII:MTB57102LQ
Nikkaji Web:J242.769I
MDL:MFCD02752619
CoE Number:11785
XlogP3-AA:0.30 (est)
Molecular Weight:114.10042000
Formula:C5 H6 O3
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
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
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1450 4-hydroxy-5-methyl-3(2H)-furanone
FLAVIS Number:13.085 (Old)
DG SANTE Food Flavourings:13.085 4-hydroxy-5-methylfuran-3(2H)-one
FEMA Number:3635 4-hydroxy-5-methyl-3(2H)-furanone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 4-HYDROXY-5-METHYL-3(2H)-FURANONE
 
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 mm/Hg @ 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:
Odor Type: caramellic
Odor Strength:high ,
recommend smelling in a 10.00 % solution or less
Substantivity:83 hour(s) at 10.00 % in dipropylene glycol
sweet cotton candy sugar burnt sugar sugar caramellic bready
Odor Description:at 10.00 % in dipropylene glycol. sweet cotton candy sugar caramel bready
Luebke, William tgsc, (2007)
Odor sample from: Sigma-Aldrich
Flavor Type: caramellic
caramellic cotton candy maple sugar burnt sugar coffee roasted coffee fenugreek
Taste Description: sweet caramellic cotton candy maple burnt sugar roasted coffee
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Advanced Biotech
CHICORY FURANONE 5% IN PG NATURAL
Odor: Celery
Advanced Biotech
CHICORY FURANONE 5% IN PG SYNTHETIC
Odor: Alcoholic, Chicory
Advanced Biotech
CHICORY FURANONE SYNTHETIC
98% min.
Odor: Celery, Chicory
Anhui Haibei
4-Hydroxy-5-methyl-3(2H)-furanone
Odor: Caramel sugar roast
Aromiens International
Chicory Furanone
Beijing Lys Chemicals
4-Hydroxy-5-methyl-3-(2H)furanone
BOC Sciences
For experimental / research use only.
4-Hydroxy-5-methyl-3-furanone
Carbosynth
For experimental / research use only.
4-Hydroxy-5-methyl-3-furanone
Ernesto Ventós
METHYL FURANEOL (CHICORY FURANONE)
Odor: FRUITY, CARAMEL, ROASTED BREAD
H. Interdonati, Inc.
Chicory Furanone Kosher
Featured Products
Jiangyin Healthway
4-Hydroxy-5-methyl-3(2H)furanone
New functional food ingredients
M&U International
CHICORY FURANEOL, Kosher
Penta International
4-HYDROXY-5-METHYL-3-(2H)-FURANONE NATURAL 5% IN ETHYL ALCOHOL, Kosher
Penta International
4-HYDROXY-5-METHYL-3-(2H)-FURANONE, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
4-Hydroxy-5-methyl-3-furanone
Sigma-Aldrich
4-Hydroxy-5-methyl-3-furanone, 97%, FG
Certified Food Grade Products
Sunaux International
Chicory Furaneol
Synerzine
4-Hydroxy-5-methyl-3(2H)-furanone
Tengzhou Xiang Yuan Aroma Chemicals
4-Hydroxy-5-methyl-3(2H)-furanone
Treatt
4-Hydroxy-5-Methyl-3(2H)-furanone
Kosher
 
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
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
 average usual ppmaverage 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,▀-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,▀-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
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:
 4-hydroxy-5-methylfuran-3-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:19322-27-1
Pubchem (cid):4564493
Pubchem (sid):135257955
Flavornet:19322-27-1
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB31859
FooDB:FDB008543
Export Tariff Code:2932.19.0000
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
 
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
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 4-pentenoate
FL/FR
5-
ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one
FL/FR
furfuryl acetone
FL
mango furanone
FL
menthone lactone
FL/FR
osmanthus flower absolute
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
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 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
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
caramel dione
FL
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:
FLcaramel
FRcotton candy
FLsugar
FRtobacco
FRtoffee
 
Occurrence (nature, food, other):note
 blackberry fruit
Search PMC Picture
 soy sauce
Search PMC Picture
 
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-
norfuraneol
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.
 
Notes:
Isol. from oil of figs and from guava. Beef flavouring ingredient
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