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maple furanone

Chemical Structure

General Material Information

Preferred name maple furanone
Trivial Name 5-Ethyl-3-hydroxy-4-methyl-2(5H)-furanone
Short Description 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone
Formula C7 H10 O3
CAS Number 698-10-2
Deleted CAS Number 144810-13-9
FEMA Number 3153
Flavis Number 10.023
ECHA Number 211-811-6
FDA UNII J007136N0N
Nikkaji Number J191.716A
MDL MFCD00036673
COE Number 2300
xLogP3-AA 0.90 (est)
NMR Predictor External link
JECFA Food Flavoring 222 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 698-10-2 ; 5-ETHYL-3-HYDROXY-4-METHYL-2(5H)-FURANONE
Synonyms
  • 2,4-dihydroxy-3-methyl-2-hexenoic acid gamma-lactone
  • emoxyfurone (Givaudan)
  • emoxyfurone 10% in PG (Givaudan)
  • ethyl fenugreek lactone
  • ethyl sotolon
  • ethyl sugar lactone
  • 5-ethyl-3-hydroxy-4-methyl furan-2-one
  • 5-ethyl-3-hydroxy-4-methyl-2-(5H)furanone
  • 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone
  • 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone 50% in triacetin
  • 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone, natural
  • 5-ethyl-3-hydroxy-4-methyl-2(5H)furanone
  • 5-ethyl-3-hydroxy-4-methyl-5H-furan-2-one
  • 5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one
  • 5-ethyl-3-methyl-3-hydroxy-2(5H)-furanone
  • 2-ethyl-3-methyl-4-hydroxydihydro-(2,5)-furan-5-one
  • 2-ethyl-3-methyl-4-hydroxydihydro-2,5-furan-5-one
  • 5-ethyl-4-methyl-3-hydroxy-2(5H)-furanone
  • ethyl-5 3-hydroxy 4-methyl 2 5H furanone
  • furan-2(5H)-one, 3-hydroxy-5-ethyl-4-methyl-
  • furan-2(5H)-one, 5-ethyl-3-hydroxy-4-methyl-
  • 2(5H)- furanone, 5-ethyl-3-hydroxy-4-methyl-
  • 2(5H)- furanone, 5-ethyl-3-hyroxy-4-methyl-
  • 2-hydroxy-3-methyl-gamma-2-hexenolactone
  • 3-hydroxy-4-methyl-5-ethyl-2-furanone
  • maple furanone (50% in triacetin)
  • maple furanone (neat)
  • maple furanone 1% in ETOH natural
  • maple furanone 1% in PG natural
  • maple furanone 1% in triacetin natural
  • maple furanone 3% in PG synthetic
  • maple furanone natural
  • maple furanone synthetic
  • maple furanone, neat
  • 5-ethyl-3-hydroxy-4-methyl-5H-furan-2-one
  • 2(5H)-Furanone, 5-ethyl-3-hydroxy-4-methyl-
  • 2-Hexenoic acid, 2,4-dihydroxy-3-methyl-, γ-lactone
  • 5-Ethyl-3-hydroxy-4-methyl-2(5H)-furanone
  • α-Hydroxy-β-methyl-Δα,β-γ-hexenolactone
  • Abhexone
  • α-Hydroxy-β-methyl-γ-hexenolactone
  • Homosotolone
  • 3-Hydroxy-4-methyl-5-ethyl-2(5H)-furanone
  • Abhexon
  • 2-Ethyl-4-hydroxy-3-methyl-2H-furan-5-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
5-ethyl-3-hydroxy-4-methyl-5H-furan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:698-10-2
Pubchem (cid):61199
Pubchem (sid):135018592
Flavornet:698-10-2
Publications by PubMed
Studies on the key aroma compounds in raw (unheated) and heated Japanese soy sauce.
Anti-inflammatory lanostanoids and lactone derivatives from Antrodia camphorata.
Characterization of the major odor-active compounds in Thai durian ( Durio zibethinus L. 'Monthong') by aroma extract dilution analysis and headspace gas chromatography-olfactometry.
Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA).
Simple determination of a strongly aromatic compound, sotolon, by capillary electrophoresis.
Main odorants in Jura flor-sherry wines. Relative contributions of sotolon, abhexon, and theaspirane-derived compounds.
A vibrational circular dichroism approach to the determination of the absolute configurations of flavorous 5-substituted-2(5H)-furanones.
Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds.
Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests.
Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science.
Two 2[5H]-furanones as possible signaling molecules in Lactobacillus helveticus.
Characterization of dried whey protein concentrate and isolate flavor.
Identification of potent odorants formed during the preparation of extruded potato snacks.
Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington.
Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines.
Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. laciniatus L.) blackberries.
Characterization of Trp(+) reversions in Escherichia coli strain WP2uvrA.
A comparison of mutation spectra detected by the Escherichia coli lac(+) reversion assay and the Salmonella typhimurium his(+) reversion assay.
False diagnosis of maple syrup urine disease owing to ingestion of herbal tea.
The naturally occurring furanones: formation and function from pheromone to food.
4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease.
Detection of genotoxicity of polluted sea water using shellfish and the alkaline single-cell gel electrophoresis (SCE) assay: a preliminary study.
Publications by J-Stage
Simple Determination of a Strongly Aromatic Compound, Sotolon, by Capillary Electrophoresis

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
HMDB (The Human Metabolome Database):HMDB33551
FooDB:FDB011616
Export Tariff Code:2932.19.0090
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 142.154296875
Specific gravity @ 25 °C
Pounds per Gallon 9.436 to 9.519
Refractive Index 1.486 to 1.493 @ 20 °C
Melting Point 31 to 35°C @ 760 mm Hg
Boiling Point 102 to 103°C @ 0.5 mm Hg
Boiling Point 83 to 86°C @ 0.5 mm Hg
Vapor Pressure 3.4E-5 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 93.89 °C TCC
logP (o/w) 0.213 est
Solubility
alcohol Yes
water, 7.439e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Caramellic
maple, sweet, fruity, caramellic, fenugreek, sugar brown sugar, nutty, chicory, praline, butterscotch
Odor strength very high , recommend smelling in a 0.01 % solution or less
Substantivity 400 hour(s) at 1.00 %
Luebke, William tgsc, (2017) At 0.01 % in dipropylene glycol. sweet fruity caramellic maple fenugreek brown sugar nutty chicory praline butterscotch
Mosciano, Gerard P&F 16, No. 4, 45, (1991) Sweet, fruity, sweet caramel with a maple like nuance
Flavor Type: Caramellic
maple, sweet, fruity, sugar brown sugar, fenugreek, nutty, caramellic, chicory, brown
Luebke, William tgsc, (2017) Sweet fruity brown sugar maple fenugreek nutty caramellic chicory
Mosciano, Gerard P&F 16, No. 4, 45, (1991) At 50.00 ppm. Sweet, fruity, with a brown maple note
Maple syrup type flavors. Strong, sweet, characteristic maple syrup

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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 maple furanone usage levels up to:
0.5000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 13.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 6.10 (μg/capita/day)
Structure Class: III
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: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: -1.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: -1.00000
granulated sugar: --
gravies: --
hard candy: -1.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

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):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

List of apha, beta-Unsaturated Aldehydes and Ketones representative of FGE.19 substances for Genotoxicity Testing [1] - Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF)
View page or View pdf

Flavouring Group Evaluation 217: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones[1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 217, Revision 1 (FGE.217Rev1). Consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones
View page or View pdf

Scientific Opinion on the safety and efficacy of furanones and tetrahydrofurfuryl derivatives: 5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one and 3-hydroxy-4,5-dimethylfuran-2(5H)-one (chemical group 13) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 217 Revision 2 (FGE.217Rev2), consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: lactones
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):698-10-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :61199
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5-ethyl-3-hydroxy-4-methyl-5H-furan-2-one
Chemidplus:0000698102