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strawberry furanone

Chemical Structure

General Material Information

Preferred name strawberry furanone
Trivial Name Furaneol
Short Description furaneol (Firmenich)
Formula C6 H8 O3
CAS Number 3658-77-3
FEMA Number 3174
Flavis Number 13.01
ECHA Number 222-908-8
FDA UNII 20PI8YZP7A
Nikkaji Number J13.291H
Beilstein Number 1281357
MDL MFCD00010706
COE Number 536
xLogP3-AA 0.70 (est)
NMR Predictor External link
JECFA Food Flavoring 1446 4-hydroxy-2,5-dimethyl-3(2H)-furanone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 3658-77-3 ; 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
Synonyms
  • alletone
  • alnose
  • cadion
  • carmelan (Elan)
  • dimethyl hydroxy furanone natural
  • dimethyl hydroxyfuranone
  • 2,5-dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran
  • 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one
  • 2,5-dimethyl-4-hydroxy-3(2H) furanone
  • 2,5-dimethyl-4-hydroxy-3(2H)-furanone
  • 2,5-dimethyl-4,5-dihydrofuran-3-ol-4-one
  • enhansol
  • flerueol (strawberry furanone) natural
  • furaneol (Firmenich)
  • nat. furaneol
  • furaneol (strawberry furanone) various dilutions
  • furaneol nat (Firmenich)
  • furaneol nat ex sugar
  • furaneol synthetic
  • furanone
  • 3(2H)- furanone, 4-hydroxy-2,5-dimethyl-
  • furonol (Givaudan)
  • 4-hydroxy 2.5 dimethyl 3(2H) furanone 98%, natural
  • natural hydroxy dimethyl furanone
  • 4-hydroxy-2,5-dimethyl furan-2(3H)-one
  • 4-hydroxy-2,5-dimethyl-2-hydrofuran-3-one
  • 4-hydroxy-2,5-dimethyl-3-furanone
  • 4-hydroxy-2,5-dimethyl-3(2H)-furanone
  • 4-hydroxy-2,5-dimethyl-3(2H)-furanone natural
  • hydroxy-2,5-dimethyl-3(2H)furanone
  • 4-hydroxy-2,5-dimethyl-3(2H)furanone
  • 4-hydroxy-2,5-dimethylfuran-2(3H)-one
  • 4-hydroxy-2,5-dimethylfuran-3-one
  • 4-hydroxy-2,5-dimethylfuran-3(2H)-one
  • pineapple compound
  • pineapple ketone
  • strawberry furanona
  • strawberry furanone (natural)
  • strawberry furanone natural
  • strawberry furanone synthetic
  • strawberry furanone, pure natural
  • walnut furanone
  • walnut furanone natural
  • walnut furanone synthetic
  • 4-hydroxy-2,5-dimethylfuran-3-one
  • 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-
  • 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
  • 2,5-Dimethyl-4-hydroxy-3(2H)-furanone
  • 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one
  • 4-Hydroxy-2,5-dimethyl-2H-furan-3-one
  • 2,5-Dimethyl-4,5-dihydrofuran-3-ol-4-one
  • 4-Hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one
  • Furaneol
  • 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran
  • 4-Hydroxy-2,5-Dimethyl-3-oxo-2,3-dihydrofuran
  • 4-Hydroxy-2,5-dimethyl-3-furanone
  • 2,5-Dimethyl-4-hydroxy-3-oxo-(2H)-furan

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

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Literature & References

Leffingwell:Chirality or Article
4-hydroxy-2,5-dimethylfuran-3-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:3658-77-3
Pubchem (cid):19309
Pubchem (sid):134985325
Flavornet:3658-77-3
Publications by Google Patents
Ethyl ester, citrus oil, 4-hydroxy-2,5-dimethyl-3-furanone, fruit flavor
Pineapple ketone carbonate derivatives
Pineapple ketone 1'-alkoxyalkyl derivatives
Publications by PubMed
Metabolic responses of Lactobacillus plantarum strains during fermentation and storage of vegetable and fruit juices.
An oxidoreductase from 'Alphonso' mango catalyzing biosynthesis of furaneol and reduction of reactive carbonyls.
An in vitro study reveals nutraceutical properties of Ananas comosus (L.) Merr. var. Mauritius fruit residue beneficial to diabetes.
Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone.
Furanone-containing poly(vinyl alcohol) nanofibers for cell-adhesion inhibition.
Changes in the bound aroma profiles of 'Hayward' and 'Hort16A' kiwifruit (Actinidia spp.) during ripening and GC-olfactometry analysis.
Genetic analysis of strawberry fruit aroma and identification of O-methyltransferase FaOMT as the locus controlling natural variation in mesifurane content.
Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry.
Evaluation of volatiles from two subtropical strawberry cultivars using GC-olfactometry, GC-MS odor activity values, and sensory analysis.
Characterization of the bound volatile extract from baby kiwi (Actinidia arguta).
Characteristic aroma compounds from different pineapple parts.
Monitoring the plant epiphyte Methylobacterium extorquens DSM 21961 by real-time PCR and its influence on the strawberry flavor.
Strawberry consumption is associated with increased antioxidant capacity in serum.
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.
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.
Stereochemical studies of odorous 2-substituted-3(2H)-furanones by vibrational circular dichroism.
Quantification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone using solid-phase extraction and direct microvial insert thermal desorption gas chromatography-mass spectrometry.
Differences in odor-active compounds of trincadeira wines obtained from five different clones.
Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate.
Mechanisms of melanogenesis inhibition by 2,5-dimethyl-4-hydroxy-3(2H)-furanone.
Functional characterization of enone oxidoreductases from strawberry and tomato fruit.
Hypolipidemic mechanisms of Ananas comosus L. leaves in mice: different from fibrates but similar to statins.
FaGT2: a multifunctional enzyme from strawberry (Fragaria x ananassa) fruits involved in the metabolism of natural and xenobiotic compounds.
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.
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens.
Up- and down-regulation of Fragaria x ananassa O-methyltransferase: impacts on furanone and phenylpropanoid metabolism.
FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase.
2,5-Dimethyl-4-hydroxy-3(2H)-furanone as a secondary metabolite from D-fructose-1,6-diphosphate metabolism by Zygosaccharomyces rouxii.
Characterization of dried whey protein concentrate and isolate flavor.
Concurrent phenomena contributing to the formation of the aroma of wine during aging in oak wood: an analytical study.
Impact of growing environment on chickasaw blackberry (Rubus L.) aroma evaluated by gas chromatography olfactometry dilution analysis.
Influence of strawberry yogurt composition on aroma release.
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.
Quantitative determination of sotolon, maltol and free furaneol in wine by solid-phase extraction and gas chromatography-ion-trap mass spectrometry.
Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis.
Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. laciniatus L.) blackberries.
Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits.
Aroma biosynthesis in strawberry: s-adenosylmethionine:furaneol o-methyltransferase activity in ripening fruits.
Volatile flavor components of stored nonfat dry milk.
Effect of food reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and hydroxyhydroquinone (HHQ), on lipid peroxidation and type IV and I allergy responses of mouse.
Stability of thiols in an aqueous process flavoring.
Aroma-active components of nonfat dry milk.
Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2h)-furanone in strawberry fruits.
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.
Oxygenated monoterpenoids from badea (Passiflora quadrangularis) fruit pulp.
Biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and derivatives in in vitro grown strawberries.
The naturally occurring furanones: formation and function from pheromone to food.
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.
Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II).
Identification of 2,5-dimethyl-4-hydroxy-3[2H]-furanone beta-D-glucuronide as the major metabolite of a strawberry flavour constituent in humans.
2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-beta-D-glucopyranoside in strawberry fruits.
DNA strand break by 2,5-dimethyl-4-hydroxy-3(2H)-furanone, a fragrant compound in various foodstuffs.
Publications by J-Stage
Hypolipidemic Mechanisms of Ananas comosus L. Leaves in Mice: Different From Fibrates but Similar to Statins
2, 5-Dimethyl-4-Hydroxy-3(2H)-Furanone as a Secondary Metabolite from D-Fructose-1, 6-Diphosphate Metabolism by Zygosaccharomyces rouxii

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
CHEMBL:View
KEGG (GenomeNet):C20717
HMDB (The Human Metabolome Database):Search
YMDB (Yeast Metabolome Database):YMDB01694
Export Tariff Code:2932.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia: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 Yes
Molecular weight 128.1273651123
Melting Point 78 to 81°C @ 760 mm Hg
Acid Value 3 max KOH/g
Vapor Pressure 0.032 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) -0.076 est
Shelf life 12 months (or longer if stored properly.)
Storage notes Store under nitrogen.
Solubility
alcohol Yes
dipropylene glycol Yes
propylene glycol Yes
water, 1.85e+004 mg/L @ 25 °C (est) Yes
paraffin oil No
isopropyl myristate No

Organoleptic Properties

Odor Type: Caramellic
sweet, cotton candy, caramellic, strawberry, sugar brown sugar, burnt, brown, savory
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity 320 hour(s) at 20.00 % in dipropylene glycol
Luebke, William tgsc, (1995) At 1.00 % in propylene glycol. sweet cotton candy caramel strawberry sugar
Mosciano, Gerard P&F 21, No. 5, 49, (1996) At 0.10 %. Sweet, slightly burnt brown caramellic, cotton candy with a savory nuance
Flavor Type: Caramellic
sweet, caramellic, sugar burnt sugar, sugar brown sugar, maple, sugar, tropical, cotton candy, cooked, meaty, fruity
Luebke, William tgsc, (1995) Sweet caramellic burnt sugar brown sugar maple sugar tropical cotton candy
Mosciano, Gerard P&F 21, No. 5, 49, (1996) At 0.10 - 1.00 ppm. Sweet caramellic cooked meaty and fruity nuances
General comment Sweet, caramel-fruity (pineapple-like), fried meat aspects brown, caramellic, jammy, cotton candy, sugary

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-mouse LD50 1608 mg/kg
Zhonghua Yufangyixue Zazhi. Chinese Journal of Preventive Medicine. Vol. 22, Pg. 85, 1988.

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
IFRA Critical Effect:
Dermal sensitization and systemic toxicity
View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.045 %
Category 2: Products applied to the axillae
0.014 %
Category 3: Products applied to the face/body using fingertips
0.27 %
Category 4: Products related to fine fragrance
0.25 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.064 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.064 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.064 %
Category 5D: Baby Creams, baby Oils and baby talc
0.064 %
Category 6: Products with oral and lip exposure
0.15 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.52 %
Category 7B: Leave-on products applied to the hair with some hand contact
0.52 %
Category 8: Products with significant anogenital exposure
0.021 %
Category 9: Products with body and hand exposure, primarily rinse off
0.49 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
0.49 %
Category 10B: Household aerosol/spray products
1.80 %
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
0.021 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
0.021 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
No Restriction
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Maximised Survey-derived Daily Intakes (MSDI-EU): 960.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 5203.00 (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: 4. Update in publication number(s): 12, 29
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: 4.0000010.00000
beverages(nonalcoholic): 5.0000080.00000
beverages(alcoholic): 43.00000180.00000
breakfast cereal: --
cheese: --
chewing gum: 100.000001000.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: 0.100000.50000
fish products: --
frozen dairy: 5.0000010.00000
fruit ices: --
gelatins / puddings: 10.0000080.00000
granulated sugar: --
gravies: --
hard candy: 10.0000010.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: 0.600000.60000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 1.0000010.00000
snack foods: --
soft candy: 20.0000060.00000
soups: --
sugar substitutes: --
sweet sauces: 5.0000040.00000

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):

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 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 the safety and efficacy of furanones and tetrahydrofurfuryl derivatives: 4-hydroxy-2,5-dimethylfuran-3(2H)-one, 4,5-dihydro-2-methylfuran-3(2H)-one, 4-acetoxy-2,5-dimethylfuran-3(2H)-one and linalool oxide (chemical group 13) when used as flavourings for all animal species
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 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 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):3658-77-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :19309
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-hydroxy-2,5-dimethylfuran-3-one
Chemidplus:0003658773
RTECS:LU3990000 for cas# 3658-77-3