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levulinic acid

Chemical Structure

General Material Information

Preferred name levulinic acid
Trivial Name Levulinic acid
Short Description 4-oxovaleric acid
Formula C5 H8 O3
CAS Number 123-76-2
FEMA Number 2627
Flavis Number 8.023
ECHA Number 204-649-2
FDA UNII RYX5QG61EI
Nikkaji Number J10.067F
Beilstein Number 0506796
MDL MFCD00002796
COE Number 23
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 606 levulinic acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 123-76-2 ; LEVULINIC ACID
Synonyms
  • acetopropionic acid
  • 3-acetyl propionic acid
  • beta- acetyl propionic acid
  • 3-acetyl propionsaeure
  • 3-acetylpropionic acid
  • b- acetylpropionic acid
  • 3-acetylpropionsaeure
  • acidum laevulinicum
  • antithermin
  • 3-keto butane-1-carboxylic acid
  • laevulic acid
  • laevulinic acid
  • levulic acid
  • levulinic acid natural
  • 4-keto pentanoic acid
  • 4-oxo pentanoic acid
  • gamma-oxo pentanoic acid
  • pentanoic acid, 4-oxo-
  • propionic acid, 3-acetyl-
  • 4-keto valeric acid
  • 4-oxo valeric acid
  • g-keto valeric acid
  • gamma-keto valeric acid
  • valeric acid, 4-oxo-
  • 4-oxopentanoic acid
  • β-Acetylpropionic acid
  • γ-Ketovaleric acid
  • 3-Acetylpropionic acid
  • 4-Oxovaleric acid
  • 4-Ketovaleric acid
  • NSC 3716
  • 3-Oxobutanecarboxylic acid
  • 3-Acetylpropanoic acid
  • Lev-OH

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

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Literature & References

4-oxopentanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:123-76-2
Pubchem (cid):11579
Pubchem (sid):134974742
Publications by PubMed
Sunflower-based biorefinery: Poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate) production from crude glycerol, sunflower meal and levulinic acid.
Efficacy of wash solutions in recovering Cyclospora cayetanensis, Cryptosporidium parvum, and Toxoplasma gondii from basil.
Tolerance of the nanocellulose-producing bacterium Gluconacetobacter xylinus to lignocellulose-derived acids and aldehydes.
Wheat bran biorefinery: an investigation on the starch derived glucose extraction accompanied by pre- and post-treatment steps.
Immersion in antimicrobial solutions reduces Salmonella enterica and Shiga toxin-producing Escherichia coli on beef cheek meat.
Reductions of Shiga toxin-producing Escherichia coli and Salmonella typhimurium on beef trim by lactic acid, levulinic acid, and sodium dodecyl sulfate treatments.
Transfer of foodborne pathogens during mechanical slicing and their inactivation by levulinic acid-based sanitizer on slicers.
Efficacy of a Levulinic Acid Plus Sodium Dodecyl Sulfate (SDS)-Based Sanitizer on Inactivation of Influenza A Virus on Eggshells.
Evaluation of levulinic acid and sodium dodecyl sulfate as a sanitizer for use in processing Georgia-grown cantaloupes.
Additive approach for inactivation of Escherichia coli O157:H7, Salmonella, and Shigella spp. on contaminated fresh fruits and vegetables using bacteriophage cocktail and produce wash.
Efficacy of sanitizers in reducing Salmonella on pecan nutmeats during cracking and shelling.
Effects of buffered vinegar and sodium dodecyl sulfate plus levulinic acid on Salmonella Typhimurium survival, shelf-life, and sensory characteristics of ground beef patties.
Feasibility of anaerobic digestion from bioethanol fermentation residue.
Reactivity of thermally treated α-dicarbonyl compounds.
Sanitizer efficacy against murine norovirus, a surrogate for human norovirus, on stainless steel surfaces when using three application methods.
Evaluation of sanitizers for inactivating Salmonella on in-shell pecans and pecan nutmeats.
Efficacy of a levulinic acid plus sodium dodecyl sulfate-based sanitizer on inactivation of human norovirus surrogates.
Inactivation of salmonella on tomato stem scars by edible chitosan and organic Acid coatings.
Inactivation of salmonella in biofilms and on chicken cages and preharvest poultry by levulinic Acid and sodium dodecyl sulfate.
Effect of pretreatment severity on the conversion of barley straw to fermentable substrates and the release of inhibitory compounds.
Acids in combination with sodium dodecyl sulfate caused quality deterioration of fresh-cut iceberg lettuce during storage in modified atmosphere package.
Organic acids associated with saccharification of cellulosic wastes during solid-state fermentation.
Efficacy of washing meat surfaces with 2% levulinic, acetic, or lactic acid for pathogen decontamination and residual growth inhibition.
Efficacy of levulinic acid-sodium dodecyl sulfate against Encephalitozoon intestinalis, Escherichia coli O157:H7, and Cryptosporidium parvum.
Inactivation of Escherichia coli O157:H7 and Salmonella typhimurium DT 104 on alfalfa seeds by levulinic acid and sodium dodecyl sulfate.
Thermal degradation characteristics and antioxidant activity of fructose solution with heating temperature and time.
Hydrolysis behavior of bamboo fiber in formic acid reaction system.
Sucrose: A prospering and sustainable organic raw material.
Inactivation of Salmonella and Escherichia coli O157:H7 on lettuce and poultry skin by combinations of levulinic acid and sodium dodecyl sulfate.
Control of Listeria monocytogenes in ready-to-eat meats containing sodium levulinate, sodium lactate, or a combination of sodium lactate and sodium diacetate.
Ester hydroxy derivatives of methyl oleate: tribological, oxidation and low temperature properties.
Interference by methyl levulinate in determination of total fat in low-fat, high-sugar products by gas chromatographic fatty acid methyl ester (GC-FAME) analysis.
Marginal zinc deficiency and changes in behavioral salt taste threshold and salt preference in mice.
[Turnover of microsomal hemeproteins in the guinea pig liver during food sensitization].
[Influence of theophylline on hexachlorobenzene induced porphyria (author's transl)].

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
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB00720
FooDB:FDB003296
Export Tariff Code:2918.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
FAO:Levulinic acid

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 116.11636352539
Specific gravity @ 25 °C
Pounds per Gallon 9.469 to 9.553
Refractive Index 1.435 to 1.445 @ 20 °C
Melting Point 30 to 33°C @ 760 mm Hg
Boiling Point 245 to 246°C @ 760 mm Hg
Vapor Pressure 0.011 mmHg @ 25 °C
Flash Point TCC Value 137.78 °C TCC
logP (o/w) -0.49
Solubility
alcohol Yes
oils Yes
water, 6.746e+005 mg/L @ 25 °C (est) Yes
paraffin oil No

Organoleptic Properties

Odor Type: Caramellic
sweet, caramellic, acidic, buttery, guaiacol, creamy, vanilla
Odor strength medium
Substantivity 400 hour(s) at 20.00 %
Luebke, William tgsc, (1982) At 100.00 %. sweet caramel acidic acetoin buttery
Mosciano, Gerard P&F 14, No. 6, 47, (1989) Sweet, guaiacol-like, creamy, acidic and slight vanillin-like
Flavor Type: Acidic
acidic, sweet, creamy, dairy
Mosciano, Gerard P&F 14, No. 6, 47, (1989) At 70.00 ppm. Acidic, sweet, creamy and slight dairy

Occurrences

Potential Uses

Applications
Flavoring purposes Butterscotch, Caramel, Maple, Sugar brown sugar
Other purposes Skin conditioning
Cosmetic purposes Perfuming agents, Skin conditioning

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:
oral-rat LD50 1850 mg/kg
(Moreno, 1977j)

intraperitoneal-mouse LD50 450 mg/kg
National Technical Information Service. Vol. AD607-952

oral-rat LD50 1850 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic, 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
Maximised Survey-derived Daily Intakes (MSDI-EU): 190.00 (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: -53.00000
beverages(nonalcoholic): -14.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -14.00000
fruit ices: -14.00000
gelatins / puddings: -4.00000
granulated sugar: --
gravies: --
hard candy: -53.00000
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):123-76-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11579
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-oxopentanoic acid
Chemidplus:0000123762
RTECS:OI1575000 for cas# 123-76-2