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ethyl levulinate

Chemical Structure

General Material Information

Preferred name ethyl levulinate
Trivial Name Ethyl levulinate
Short Description ethyl 4-oxovalerate
Formula C7 H12 O3
CAS Number 539-88-8
FEMA Number 2442
Flavis Number 9.435
ECHA Number 208-728-2
FDA UNII 7BU24CSS2G
Nikkaji Number J1.595D
Beilstein Number 0507641
MDL MFCD00009209
COE Number 373
xLogP3-AA 0.10 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 607 ethyl levulinate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 539-88-8 ; ETHYL LEVULINATE
Synonyms
  • ethyl 3-acetyl propionate
  • ethyl 4-ketovalerate
  • ethyl 4-oxopentanoate
  • ethyl 4-oxovalerate
  • ethyl acetyl propanoate
  • ethyl acetylpropanoate
  • ethyl ketovalerate
  • ethyl laevulate
  • ethyl levulate
  • ethyl levulinate FCC
  • ethyl levulinate natural
  • ethyl-4-oxovalerate
  • ethyl-levulinate
  • laevulic acid ethyl ester
  • levulinic acid ethyl ester
  • 4-oxo- pentanoic acid ethyl ester
  • pentanoic acid, 4-oxo-, ethyl ester
  • 4-keto valeric acid ethyl ester
  • 4-oxo valeric acid ethyl ester
  • Levulinic acid, ethyl ester
  • Ethyl laevulinate
  • Ethyl 3-acetylpropionate
  • 4-Oxopentanoic acid ethyl ester
  • NSC 24876
  • NSC 8863
  • NXT Solv 100
  • NS 100
  • GFbio ReSolv 100

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

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Literature & References

ethyl 4-oxopentanoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:539-88-8
Pubchem (cid):10883
Pubchem (sid):134978625
Publications by PubMed
Production of ethyl levulinate by direct conversion of wheat straw in ethanol media.
Conversion of mono- and disaccharides to ethyl levulinate and ethyl pyranoside with sulfonic acid-functionalized ionic liquids.
Conversion of furfuryl alcohol into ethyl levulinate using solid acid catalysts.
Sulfonated graphene oxide as effective catalyst for conversion of 5-(hydroxymethyl)-2-furfural into biofuels.
RANEY® Ni catalyzed transfer hydrogenation of levulinate esters to γ-valerolactone at room temperature.
Efficient catalytic system for the conversion of fructose into 5-ethoxymethylfurfural.
Acid-catalyzed conversion of mono- and poly-sugars into platform chemicals: effects of molecular structure of sugar substrate.
A chemo-enzymatic route to synthesize (S)-γ-valerolactone from levulinic acid.
Synthesis and characterization of sulfated TiO2 nanorods and ZrO2/TiO2 nanocomposites for the esterification of biobased organic acid.
Production of ethyl levulinate by direct conversion of wheat straw in ethanol media.
A multifunctional 5-aminolevulinic acid derivative induces erythroid differentiation of K562 human erythroleukemic cells.
Conversion of mono- and disaccharides to ethyl levulinate and ethyl pyranoside with sulfonic acid-functionalized ionic liquids.
Comment on processes for the direct conversion of cellulose or cellulosic biomass into levulinate esters.
A three-step synthetic approach to asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b']dithiophenes.
Conversion of furfuryl alcohol into ethyl levulinate using solid acid catalysts.
Research on heterocyclic compounds, XXIX. Synthesis and antiinflammatory activity of imidazo[1,2-a]pyrazine derivatives.
Synthesis of a spin-labeled phospholipid for studying membrane dynamics in intact mammalian cells.
Polymer-linked 6-azauridine 5'-monophosphate, a resin of high bioaffinity to orotidine-5'-phosphate decarboxylase.
Substrate- and product-affinity resins for adenosine deaminase obtained by immobilisation of adenosine and inosine via 2',3'-cyclic acetal derivatives.

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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB40433
FooDB:FDB020166
Export Tariff Code:2918.30.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
FAO:Ethyl levulinate

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 144.17024230957
Boiling Point 93 to 94°C @ 18 mm Hg
Acid Value 2 max KOH/g
Vapor Pressure 0.249 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 90.56 °C TCC
logP (o/w) 0.4 est
Solubility
alcohol Yes
water, 4.566e+004 mg/L @ 25 °C (est) Yes
paraffin oil No

Organoleptic Properties

Odor Type: Fruity
sweet, fruity, floral, berry, green, pineapple, rhubarb, melon, waxy
Odor strength medium
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1995) At 100.00 %. sweet fruity floral berry green pineapple rhubarb
Mosciano, Gerard P&F 15, No. 1, 19, (1990) Fruity, green, melon-like with waxy notes
Flavor Type: Fruity
fruity, green, waxy, melon
Mosciano, Gerard P&F 15, No. 1, 19, (1990) At 40.00 ppm. Fruity, green, waxy and melon
Can be used in grape, apple, pineapple, fruit, rum, smoked-meat and gravy flavors. Fruity

Occurrences

Potential Uses

Applications
Odor purposes Apple, Grape, Green, Melon, Pear, Pineapple, Rhubarb, Saffron
Flavoring purposes Olive, Smoke
Other purposes Waxy
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
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.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
(Moreno, 1978f)

oral-rat LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 679, 1982.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 679, 1982.

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 ethyl levulinate usage levels up to:
6.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 470.00 (μg/capita/day)
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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -12.00000
beverages(nonalcoholic): -5.80000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -11.00000
fruit ices: -11.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -12.00000
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

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - 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 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): 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
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):539-88-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10883
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
ethyl 4-oxopentanoate
Chemidplus:0000539888
RTECS:OI1700000 for cas# 539-88-8