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Ethyl levulinate

PubChem CID
10883
Structure
Ethyl levulinate_small.png
Ethyl levulinate_3D_Structure.png
Molecular Formula
Synonyms
  • ETHYL LEVULINATE
  • Ethyl 4-oxopentanoate
  • 539-88-8
  • Ethyl levulate
  • Ethyl laevulinate
Molecular Weight
144.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Ethyl levulinate is an oxo carboxylic acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Ethyl levulinate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 4-oxopentanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GMEONFUTDYJSNV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCOC(=O)CCC(=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H12O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

539-88-8

2.3.2 Deprecated CAS

1790637-12-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 FEMA Number

2.3.9 HMDB ID

2.3.10 JECFA Number

607

2.3.11 Metabolomics Workbench ID

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 RXCUI

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • ethyl 4-ketovalerate
  • ethyl 4-oxopentanoate
  • ethyl acetylpropanoate
  • ethyl levulinate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
144.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
144.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
144.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
43.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
129
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid
colourless to pale yellow liquid with apple odour

3.2.2 Boiling Point

93.00 to 94.00 °C. @ 18.00 mm Hg
The Good Scents Company Information System

3.2.3 Melting Point

< 25 °C

3.2.4 Solubility

soluble in water and alcohol
1 ml in 1 ml 95% alcohol (in ethanol)

3.2.5 Density

1.009-1.014

3.2.6 Refractive Index

1.420-1.425

3.2.7 Kovats Retention Index

Standard non-polar
1029 , 1023 , 1024
Semi-standard non-polar
1020 , 1070
Standard polar
1607 , 1610 , 1607 , 1614 , 1607 , 1607 , 1602 , 1567 , 1601 , 1600

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.4.2 Fragrances

Fragrance Ingredient (Ethyl levulinate) -> IFRA transparency List

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Catalog Number
120
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
122629
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 13
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

43.0 99.99

99.0 83.40

129.0 28.30

101.0 22.70

74.0 22.60

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Notes
instrument=HITACHI M-80B
2 of 13
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

43.0 99.99

99.0 83.40

129.0 28.30

101.0 22.70

74.0 22.60

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Notes
instrument=HITACHI M-80B

4.2.2 Other MS

1 of 3
View All
Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

43 999

99 834

129 283

101 227

74 226

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License
CC BY-NC-SA
2 of 3
View All
Authors
YAMAMOTO M, DEP. CHEMISTRY, FAC. SCIENCE, NARA WOMEN'S UNIV.
Instrument
HITACHI RMU-6M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

43 999

99 553

29 211

74 194

101 156

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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A15001
Lot Number
10183696
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

1 of 2
Technique
ATR-Cylindrical Internal Reflectance (CIR)
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A15001
Lot Number
10183696
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

1 of 2
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A15001
Lot Number
10183696
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Catalog Number
122629
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

7.2 FEMA Flavor Profile

Fruit

7.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2442
GRAS Number
3, 25
JECFA Flavor Number
607

7.4 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

1 of 3
Chemical Name
ETHYL 4-OXOPENTANOATE
Evaluation Year
1999
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
2 of 3
Chemical Name
ETHYL ACETYLPROPANOATE
Evaluation Year
1999
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
3 of 3
Chemical Name
ETHYL LEVULINATE
Evaluation Year
1999
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

9.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green half-circle Green half-circle - The chemical is expected to be of low concern
Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Pentanoic acid, 4-oxo-, ethyl ester: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 91% (1583 of 1740) of all reports. Pictograms displayed are for 9% (157 of 1740) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1583 of 1740 companies (only 9% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 1740 reports by companies from 4 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 1583 of 1740 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 157 of 1740 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Not Classified

10.1.3 EPA Safer Chemical

Chemical: Ethyl levulinate

Green half-circle Green half-circle - The chemical is expected to be of low concern based on experimental and modeled data. Additional data would strengthen EPA's confidence in the chemical's safer status.

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Pentanoic acid, 4-oxo-, ethyl ester
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Ethyl levulinate: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 EPA Safer Choice

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 EPA CPDat Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 EPA DSSTox Classification

16.9 EPA TSCA and CDR Classification

16.10 EPA Substance Registry Services Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemicals under the TSCA
    Pentanoic acid, 4-oxo-, ethyl ester
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  10. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  11. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  12. ChEBI
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. EPA Chemical and Products Database (CPDat)
  15. EPA Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  16. EU Food Improvement Agents
  17. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  18. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  19. Flavor and Extract Manufacturers Association (FEMA)
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Pentanoic acid, 4-oxo-, ethyl ester
    http://www.nist.gov/srd/nist1a.cfm
  22. SpectraBase
    4-OXOPENTANOIC ACID, ETHYL ESTER
    https://spectrabase.com/spectrum/Bg7eBH42XP8
    4-Oxo-pentanoic acid ethyl ester
    https://spectrabase.com/spectrum/DnubP9h6QpU
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. MassBank Europe
  25. Metabolomics Workbench
  26. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  27. NMRShiftDB
  28. Protein Data Bank in Europe (PDBe)
  29. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  30. Springer Nature
  31. SpringerMaterials
  32. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  33. Wikidata
  34. Wikipedia
  35. Wiley
  36. PubChem
  37. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  38. GHS Classification (UNECE)
  39. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  40. EPA Substance Registry Services
  41. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  42. PATENTSCOPE (WIPO)
CONTENTS