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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:32 UTC |
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HMDB ID | HMDB0000720 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Levulinic acid |
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Description | Levulinic acid, also known as laevulinsaeure or levulate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Levulinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Levulinic acid exists in all living organisms, ranging from bacteria to humans. Levulinic acid is a sweet, acetoin, and acidic tasting compound. Outside of the human body, Levulinic acid has been detected, but not quantified in, several different foods, such as cereals and cereal products, green vegetables, fruits, alcoholic beverages, and root vegetables. This could make levulinic acid a potential biomarker for the consumption of these foods. |
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Structure | |
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Synonyms | Value | Source |
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3-Acetylpropionic acid | ChEBI | 3-Ketobutane-1-carboxylic acid | ChEBI | 4-Ketovaleric acid | ChEBI | 4-Oxovaleric acid | ChEBI | beta-Acetylpropionic acid | ChEBI | gamma-Ketovaleric acid | ChEBI | LAEVULINIC ACID | ChEBI | Laevulinsaeure | ChEBI | LEVA | ChEBI | Levulic acid | ChEBI | Levulinsaeure | ChEBI | 3-Acetylpropionate | Generator | 3-Ketobutane-1-carboxylate | Generator | 4-Ketovalerate | Generator | 4-Oxovalerate | Generator | b-Acetylpropionate | Generator | b-Acetylpropionic acid | Generator | beta-Acetylpropionate | Generator | Β-acetylpropionate | Generator | Β-acetylpropionic acid | Generator | g-Ketovalerate | Generator | g-Ketovaleric acid | Generator | gamma-Ketovalerate | Generator | Γ-ketovalerate | Generator | Γ-ketovaleric acid | Generator | LAEVULINate | Generator | Levulate | Generator | Levulinate | Generator | 4-Oxopentanoate | HMDB | 4-Oxopentanoic acid | HMDB | Diasporal | HMDB | Levulinic acid, sodium salt | HMDB | Magnesium diasporal | HMDB | Calcium levulate | HMDB | Magnesium levulinate | HMDB | Calcium levulinate | HMDB | Levulinic acid, ammonium salt | HMDB | Levulinic acid, calcium salt | HMDB | Magnesium laevulinate | HMDB | Levulinic acid | ChEBI |
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Chemical Formula | C5H8O3 |
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Average Molecular Weight | 116.1152 |
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Monoisotopic Molecular Weight | 116.047344122 |
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IUPAC Name | 4-oxopentanoic acid |
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Traditional Name | levulinic acid |
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CAS Registry Number | 123-76-2 |
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SMILES | CC(=O)CCC(O)=O |
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InChI Identifier | InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) |
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InChI Key | JOOXCMJARBKPKM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Keto acids and derivatives |
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Sub Class | Gamma-keto acids and derivatives |
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Direct Parent | Gamma-keto acids and derivatives |
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Alternative Parents | |
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Substituents | - Gamma-keto acid
- Short-chain keto acid
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 30 - 33 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -0.49 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0ug0-6900000000-ffad5af79457e68cca02 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-dd0d17209893b2b71d10 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-0b0447e3daa65b1cd932 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-e0d39a4a978220036faa | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ug0-6900000000-ffad5af79457e68cca02 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-beecc1bba7b8b0ca4201 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00fr-9500000000-8c1e2090296fa71bf0d0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00xr-9400000000-923a1fccce36ba18d088 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-01vo-9300000000-2c09d37e792efac90655 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0303-9800000000-d158f0c32e82eca0ef90 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0006-9000000000-dd0d17209893b2b71d10 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-9400000000-1043277f0ad49a5664a3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006t-9100000000-0a0fca12836c8c8ba113 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfr-9000000000-247961be84518f0ebcda | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-3900000000-b8133a0e2c97f98cef46 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01b9-9600000000-e133b145c780f2c290d3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052e-9000000000-6ff5c46cdc591b725694 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 6.691 +/- 5.255 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.87 (0.31-1.92) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 1.3 (0.4-2.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 1.28 (0.33-2.75) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 1.7 (0.6-2.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Missing teeth | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | Urine | Detected and Quantified | 8.873 +/- 7.994 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 414.784 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Missing teeth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB02239 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003296 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 11091 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Levulinic_acid |
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METLIN ID | 2195 |
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PubChem Compound | 11579 |
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PDB ID | Not Available |
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ChEBI ID | 45630 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Cai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong. Review on preparation methods of levulinic acid, a new platform chemical. Xiandai Huagong (2003), 23(4), 14-16. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome]. Nefrologia. 2004;24 Suppl 3:85-8. [PubMed:15219077 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Melgaard B, Clausen J, Rastogi SC: Heavy metal levels and delta-amino-levulinic acid dehydrase levels in peripheral polyneuropathy. Acta Neurol Scand. 1976 Apr;53(4):291-307. [PubMed:178141 ]
- Matsui M, Kaji R, Oka N, Nishio T, Kimura J: [Multifocal axonal motor neuropathy associated with anti-ganglioside antibodies]. Rinsho Shinkeigaku. 1992 Oct;32(10):1130-5. [PubMed:1297559 ]
- Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
- Keithly L, Ferris Wayne G, Cullen DM, Connolly GN: Industry research on the use and effects of levulinic acid: a case study in cigarette additives. Nicotine Tob Res. 2005 Oct;7(5):761-71. [PubMed:16191747 ]
- Endo G, Horiguchi S, Kiyota I: Urinary N-acetyl-beta-D-glucosaminidase activity in lead-exposed workers. J Appl Toxicol. 1990 Aug;10(4):235-8. [PubMed:2391405 ]
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