Compounds > ethyl levulinate
Page last updated: 2024-11-05

ethyl levulinate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Ethyl levulinate is a colorless liquid with a pleasant odor. It is a promising bio-based platform chemical derived from biomass sources like lignocellulose. Synthesis typically involves the reaction of levulinic acid with ethanol, catalyzed by acidic or enzymatic methods. Ethyl levulinate exhibits various potential applications: as a biofuel additive, a solvent for pharmaceuticals, a precursor for polymers, and a component in fragrances. Research on ethyl levulinate focuses on optimizing its production methods, exploring its versatility as a renewable chemical, and evaluating its potential for biofuel development and other green technologies. Its high biodegradability and low toxicity make it a sustainable alternative to traditional petroleum-based chemicals.'

ethyl levulinate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10883
CHEMBL ID3182933
CHEBI ID169371
SCHEMBL ID92709
MeSH IDM0538026

Synonyms (69)

Synonym
4-03-00-01562 (beilstein handbook reference)
7bu24css2g ,
unii-7bu24css2g
CHEBI:169371
pentanoic acid, 4-oxo-, ethyl ester
nsc-24876
nsc24876
ethyl acetylpropanoate
fema no. 2442
ai3-00677
brn 0507641
ethyl ketovalerate
ethyl levulinate (natural)
einecs 208-728-2
nsc 24876
nsc-8863
ethyl 4-oxovalerate
ethyl 3-acetylpropionate
ethyl laevulinate
ethyl levulinate
ethyl levulate
ethyl 4-ketovalerate
539-88-8
levulinic acid, ethyl ester
ethyl 4-oxopentanoate
nsc8863
ethyl levulinate, 99%
gmeonfutdyjsnv-uhfffaoysa-
inchi=1/c7h12o3/c1-3-10-7(9)5-4-6(2)8/h3-5h2,1-2h3
4-oxovaleric acid ethyl ester
4-ketovaleric acid ethyl ester
levulinic acid ethyl ester
3-acetylpropionic acid ethyl ester
L0120
4-oxo-pentanoic acid ethyl ester
ethyl-4-oxovalerate
NCGC00256288-01
cas-539-88-8
dtxcid6027058
dtxsid8047058 ,
tox21_302292
ethyl 4-oxidanylidenepentanoate
A829891
4-oxopentanoic acid ethyl ester
BBL009708
AKOS005716867
STL141073
FT-0625785
ethyl levulinate [fhfi]
ethyl levulinate [fcc]
ethyl levulinate [mi]
SCHEMBL92709
ethyllevulinate
W-105687
CHEMBL3182933
F0001-1401
mfcd00009209
ethyl levulinate, natural, >=98%, fg
ethyl levulinate, >=98%, fcc, fg
fema 2442
CS-W011009
DS-4184
CS-0204023
BCP30245
D77713
bkq ,
Q27268032
EN300-59517
ethyl4-oxopentanoate

Research Excerpts

Toxicity

The toxicity of levulinate esters in aquatic exposure (assessed as the EC50) increased as a function of increasing alkyl chain length. The most toxic compound for the aquatic organisms was butyl Levulinate, followed by ethyllevulinate and methyl levulinates.

ExcerptReferenceRelevance
" As a general trend, the toxicity of levulinate esters in aquatic exposure (assessed as the EC50) increased as a function of increasing alkyl chain length; accordingly, the most toxic compound for the aquatic organisms was butyl levulinate, followed by ethyl levulinate and methyl levulinate."( Ecotoxicity studies of the levulinate ester series.
Giner, B; Lomba, L; Muñiz, S; Navarro, E; Pino, MR, 2014)		0.58
" In this study, the three potential biofuels ethyl levulinate (EL), 2-methyltetrahydrofuran (2-MTHF) and 2-methylfuran (2-MF) were investigated for their acute embryo toxicity and teratogenicity using the fish embryo toxicity (FET) test to identify unknown hazard potentials and to allow focusing further research on substances with low toxic potentials."( Acute embryo toxicity and teratogenicity of three potential biofuels also used as flavor or solvent.
Anders, N; Bluhm, K; Hollert, H; Klankermayer, J; Schaeffer, A; Seiler, TB, 2016)		0.69
" 2-MF revealed the highest toxic potential with significant induction of micronuclei below 20."( Genotoxicity of three biofuel candidates compared to reference fuels.
Anders, N; Bluhm, K; Brendt, J; Heger, S; Hollert, H; Mayer, P; Redelstein, R; Schaeffer, A, 2018)		0.48

Dosage Studied

ExcerptRelevanceReference
" In this study, we evaluated the acute ecotoxicity of four levulinates (levulinic acid, methyl levulinate, ethyl levulinate and butyl levulinate) on freshwater algae (Chlamydomonas reinhardtii), bacteria (Vibrio fischeri), daphnids (Daphnia magna) and earthworms (Eisenia foetida) using various dose-response tests."( Ecotoxicity studies of the levulinate ester series.
Giner, B; Lomba, L; Muñiz, S; Navarro, E; Pino, MR, 2014)		0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
oxo carboxylic acidAny compound that has an aldehydic or ketonic group as well as a carboxylic acid group in the same molecule.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency48.55770.000229.305416,493.5996AID743079
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency3.88950.001019.414170.9645AID743191
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (9.52)29.6817
2010's15 (71.43)24.3611
2020's4 (19.05)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 63.18

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index63.18 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index5.22 (4.65)
Search Engine Demand Index100.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (63.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (95.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glycerol
Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.		7.5920alditol;
triol		algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		7.610elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
nickel
Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.		2.5720metal allergen;
nickel group element atom		epitope;
micronutrient
sulfuric acid
sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.		3.0640sulfur oxoacidcatalyst
ether
Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.		2.1110ether;
volatile organic compound		inhalation anaesthetic;
non-polar solvent;
refrigerant
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		2.1110chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
2-methyltetrahydrofuran
2-methyltetrahydrofuran: structure in first source		2.8330
furfuryl alcohol
furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.		2.520furans;
primary alcohol		Maillard reaction product
furaldehyde
Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.		2.930aldehyde;
furans		Maillard reaction product;
metabolite
gamma-valerolactone
gamma-valerolactone: metabolite of n-hexane; RN given refers to cpd with methyl moiety in position 5. gamma-valerolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane.		2.8430butan-4-olideflavouring agent;
human xenobiotic metabolite
ethyl formate
ethyl formate : A formate ester resulting from the formal condensation of formic acid with ethanol.. ethoxycarbonyl group : An organyl group of formula -COOEt.		2.1110ethyl ester;
formate ester		fumigant;
plant metabolite
2-methylfuran
2-methylfuran : A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a methyl group.		2.5520furans;
volatile organic compound		flavouring agent;
fuel;
hepatotoxic agent;
human urinary metabolite;
plant metabolite
levulinic acid
levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.		2.0810oxopentanoic acid;
straight-chain saturated fatty acid		plant metabolite
zirconium
Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.		2.110titanium group element atom
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.17101,2,3-triazole
methyl levulinate
methyl levulinate: structure in first source		2.110oxo carboxylic acid
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		2.4110cobalt group element atom;
metal allergen		micronutrient
lignin
Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.		7.610
5-hydroxymethylfurfural
5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.		2.5720arenecarbaldehyde;
furans;
primary alcohol		indicator;
Maillard reaction product
uniconazole
uniconazole: structural analog of diniconazole; RN refers to ((E)-(+-))-isomer; structure given in first source. uniconazole : A racemate comprising equimolar amounts of uniconazole-P and its enantiomer, (R)-uniconazole.. (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol : A member of the class of triazoles that is 1,2,4-triazole which is substituted at position 1 by a 1-(p-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl group.		7.1710monochlorobenzenes;
secondary alcohol;
triazoles
zeolites
[no description available]		2.5320
aluminum oxide
Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.		2.1310
cellulose
DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.		2.7730glycoside
ConditionIndicatedRelationship StrengthStudiesTrials
Chromosome-Defective Micronuclei
[description not available]		02.1710