Basic information
- Standard SMILES
CCOC(=O)CCC(C)=O- InChIKey
GMEONFUTDYJSNV-UHFFFAOYSA-N- Molecular formula
- C7H12O3
- Average molar mass
- 144.17 g/mol
- Monoisotopic mass
- 144.07864424
Overview
Ethyl levulinate is an oxo carboxylic acid.
Names & identifiers
- Preferred name
- Ethyl levulinate
- IUPAC
- ethyl 4-oxopentanoate
- English name
- Ethyl levulinate
- Molecular formula
- C7H12O3
- Molecular weight
- 144.17
Names & synonyms
ETHYL LEVULINATEEthyl 4-oxopentanoate539-88-8Ethyl 4-ketovalerateEthyl 4-oxovalerateLevulinic acid, ethyl esterPentanoic acid, 4-oxo-, ethyl esterEthyl acetylpropanoateFEMA No. 2442DTXSID80470587BU24CSS2GNSC-24876
Show more names
ELAFEMA 24424-oxo-pentanoicaciethylesterPentanoicacid,4-oxo-,ethylesterinateethyllevulate
DTXCID6027058RefChem:138978208-728-2Ethyl levulateEthyl laevulinateEthyl 3-acetylpropionateEthyl ketovalerateethyllevulinate
Database identifiers
- CAS
539-88-8- PubChem CID
- 10883
- DTXSID
DTXSID8047058- ChEMBL
CHEMBL3182933- ChEBI
CHEBI:169371- UNII
- 7BU24CSS2G
- EC Number
- 208-728-2
- Nikkaji
- J1.595D
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 129
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Ethyl levulinate) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.009-1.014
Flavoring AgentsEU Flavoring substances
Solubility
soluble in water and alcohol
1 ml in 1 ml 95% alcohol (in ethanol)
Boiling Point
93.00 to 94.00 °C. @ 18.00 mm Hg
93-94 °C (18 mm Hg); 105 °C (24 mm Hg)
Melting Point< 25 °C
Refractive Index1.420-1.425
Physical Description
Solid
colourless to pale yellow liquid with apple odour
Physicochemical properties
- Melting point
- 25 °C · <25 °C
- Boiling point
- 93 · 93-94 °C/18 mmHg (lit.)
- Density
- 1.016 g/mL · 1.016 g/mL at 25 °C (lit.)
- vapor pressure
- 11 Pa · 11Pa at 25℃
- FEMA
- 2442 · 2442 | ETHYL LEVULINATE
- refractive index
- 20 · n20/D 1.422(lit.)
- FLAVIS Number
- 9.435 · 09.435 | Ethyl 4-oxovalerate
- Flash point
- 195 °F · 195 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 2 O: · H2O: freely soluble
- form
- Liquid
- color
- Clear yellow
- Specific Gravity
- 1.01 · 1.01
- Odor
- 100 % · at 100.00 %. sweet fruity floral berry green pineapple rhubarb
- Odor Type
- fruity
- biological source
- synthetic
- Water Solubility
- Soluble in water.
- Merck
- 14 · 14,3819
- JECFA Number
- 607 · 607
- BRN
- 507641 · 507641
- Dielectric constant
- 12 · 12.0(21℃)
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - EMOLLIENTPERFUMINGSOLVENT
- InChI
- 1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3
- InChIKey
- GMEONFUTDYJSNV-UHFFFAOYSA-N
- SMILES
- CCOC(=O)CCC(C)=O
- LogP
- 0.324 at · 0.324 at 20℃
- Surface tension
- 33.25 mN/m · 33.25mN/m at 293.15K
- CAS DataBase Reference
- 539 · 539-88-8(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ETHYL LEVULINATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 BU24CSS2G · 7BU24CSS2G
- NIST Chemistry Reference
- 4 · Pentanoic acid, 4-oxo-, ethyl ester(539-88-8)
- EPA Substance Registry System
- 4 · Pentanoic acid, 4-oxo-, ethyl ester (539-88-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 24 · 24/25
- WGK Germany
- 2 · 2
- RTECS
- 1700000 · OI1700000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29183000 · 29183000
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 90% (1583 of 1758) of all reports.
Not Classified
Aggregated GHS information provided per 1758 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Pentanoic acid, 4-oxo-, ethyl ester
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 26-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23920
Ethyl levulinate: Does not have an individual approval but may be used under an appropriate group standard
EPA Safer ChemicalChemical: Ethyl levulinate
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- OI1700000
- hs_code
- 29183000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H315-H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Use Classification
EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPentanoic acid, 4-oxo-, ethyl ester: ACTIVE
Applications
OccurrenceReported found in white bread, roasted onion, wheat bread, cognac, malt whiskey, grape wines, cocoa, bilberry wine, Bourbon vanilla and cherimoya (Annona cheremolia Mill.).
UsesSolvent for cellulose acetate and starch ethers, flavoring.
UsesEthyl levulinate is used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts
UsesEthyl levulinate was used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts.
General DescriptionEthyl levulinate is diluent for biodiesel fuels with high saturated fatty acid content.
Preparation methods
PreparationUsually obtained by direct esterification of levulinic acid with ethanol and H2SO4 in benzene or in toluene; also in the presence of HCI in ethanol; other methods starting from glucose, fructose and others are of less importance.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: Ethyl levulinate is an oxo carboxylic acid.
Related reactions
65 records
Linked notes
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