Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:10:04 UTC |
---|
Update date | 2020-09-17 15:38:09 UTC |
---|
Primary ID | FDB012250 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | 3-Methyl-2-oxobutanoic acid |
---|
Description | alpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a fruity tasting compound. Outside of the human body, alpha-Ketoisovaleric acid has been detected, but not quantified in, several different foods, such as root vegetables, jerusalem artichokes, rapinis, chia, and cowpea. This could make alpha-ketoisovaleric acid a potential biomarker for the consumption of these foods. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid. |
---|
CAS Number | 759-05-7 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
2-Keto-3-methylbutyric acid | ChEBI | 2-Ketoisovaleric acid | ChEBI | 2-Ketovaline | ChEBI | 2-oxo-3-Methylbutanoic acid | ChEBI | 2-oxo-3-Methylbutyric acid | ChEBI | 2-Oxoisovaleric acid | ChEBI | 3-Methyl-2-oxobutanoate | ChEBI | 3-Methyl-2-oxobutyric acid | ChEBI | alpha-Keto-isovaleric acid | ChEBI | alpha-Ketovaline | ChEBI | alpha-oxo-beta-Methylbutyricacid | ChEBI | alpha-Oxoisovaleric acid | ChEBI | Dimethylpyruvic acid | ChEBI | Isopropylglyoxylic acid | ChEBI | 2-oxo-3-Methylbutanoate | Kegg | 2-Oxoisovalerate | Kegg | 2-Oxoisopentanoate | Kegg | 2-Keto-3-methylbutyrate | Generator | 2-Ketoisovalerate | Generator | 2-oxo-3-Methylbutyrate | Generator | 3-Methyl-2-oxobutanoic acid | Generator | 3-Methyl-2-oxobutyrate | Generator | a-Keto-isovalerate | Generator | a-Keto-isovaleric acid | Generator | alpha-Keto-isovalerate | Generator | Α-keto-isovalerate | Generator | Α-keto-isovaleric acid | Generator | a-Ketovaline | Generator | Α-ketovaline | Generator | a-oxo-b-Methylbutyricacid | Generator | Α-oxo-β-methylbutyricacid | Generator | a-Oxoisovalerate | Generator | a-Oxoisovaleric acid | Generator | alpha-Oxoisovalerate | Generator | Α-oxoisovalerate | Generator | Α-oxoisovaleric acid | Generator | Dimethylpyruvate | Generator | Isopropylglyoxylate | Generator | 2-Oxoisopentanoic acid | Generator | a-Ketoisovalerate | Generator | a-Ketoisovaleric acid | Generator | alpha-Ketoisovalerate | Generator | Α-ketoisovalerate | Generator | Α-ketoisovaleric acid | Generator | 2-Ketoisvaleric acid | HMDB | 2-oxo-3-Methyl-butyrate | HMDB | 3-Methyl-2-oxo-butanoate | HMDB | 3-Methyl-2-oxo-butanoic acid | HMDB | 3-Methyl-2-oxo-butyrate | HMDB | 3-Methyl-2-oxo-butyric acid | HMDB | 3-Methyl-2-oxobutinoate | HMDB | 3-Methyl-2-oxobutinoic acid | HMDB | a-Keto-b-methylbutyrate | HMDB | a-Keto-b-methylbutyric acid | HMDB | a-oxo-b-Methylbutyrate | HMDB | a-oxo-b-Methylbutyric acid | HMDB | alpha-Keto-beta-methylbutyrate | HMDB | alpha-Keto-beta-methylbutyric acid | HMDB | alpha-oxo-beta-Methylbutyrate | HMDB | alpha-oxo-beta-Methylbutyric acid | HMDB | Ketovaline | HMDB | alpha-Ketoisopentanoic acid | HMDB | alpha-Ketoisovaleric acid | Generator, MeSH | 2-keto-3-Methylbutyrate | biospider | 2-keto-3-Methylbutyric acid | ChEBI | 2-KETO-ISOVALERATE | biospider | 2-Oxo-3-methylbutanoic acid | biospider | 2-Oxo-3-methylbutyrate | biospider | 2-Oxo-3-methylbutyric acid | biospider | 3-methyl-2-oxo-Butanoate | biospider | 3-methyl-2-oxo-Butanoic acid | biospider | 3-methyl-2-oxo-Butyrate | biospider | 3-methyl-2-oxo-Butyric acid | biospider | A-keto-b-methylbutyrate | biospider | A-keto-b-methylbutyric acid | biospider | A-keto-isovalerate | biospider | A-keto-isovaleric acid | biospider | A-ketoisovalerate | biospider | A-oxo-b-methylbutyrate | biospider | A-oxo-b-methylbutyric acid | biospider | A-oxoisovalerate | biospider | A-oxoisovaleric acid | biospider | Alpha-keto-beta-methylbutyrate | biospider | Alpha-keto-beta-methylbutyric acid | biospider | Alpha-keto-isovalerate | biospider | Alpha-keto-isovaleric acid | biospider | Alpha-keto-valine | biospider | Alpha-ketoisopentanoic acid | biospider | Alpha-ketoisovalerate | biospider | Alpha-ketoisovaleric acid | biospider | Alpha-oxo-beta-methylbutyrate | biospider | Alpha-oxo-beta-methylbutyric acid | biospider | Alpha-oxoisovalerate | biospider | Alpha-oxoisovaleric acid | biospider | Butanoic acid, 3-methyl-2-oxo- | biospider | FEMA 3869 | db_source | KIV | biospider | α-keto-isovalerate | Generator | α-keto-isovaleric acid | Generator | α-ketovaline | Generator | α-oxo-β-methylbutyricacid | Generator | α-oxoisovalerate | Generator | α-oxoisovaleric acid | Generator |
|
---|
Predicted Properties | |
---|
Chemical Formula | C5H8O3 |
---|
IUPAC name | 3-methyl-2-oxobutanoic acid |
---|
InChI Identifier | InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) |
---|
InChI Key | QHKABHOOEWYVLI-UHFFFAOYSA-N |
---|
Isomeric SMILES | CC(C)C(=O)C(O)=O |
---|
Average Molecular Weight | 116.1152 |
---|
Monoisotopic Molecular Weight | 116.047344122 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Keto acids and derivatives |
---|
Sub Class | Short-chain keto acids and derivatives |
---|
Direct Parent | Short-chain keto acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Branched fatty acid
- Methyl-branched fatty acid
- Short-chain keto acid
- Alpha-keto acid
- Fatty acyl
- Alpha-hydroxy ketone
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Indirect biological role: Biological role: Industrial application: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 51.72%; H 6.94%; O 41.34% | DFC |
---|
Melting Point | Mp 31° | DFC |
---|
Boiling Point | Bp 170.5° | DFC |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9500000000-ff936b879a69b5d118f8 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-8920000000-e37b37d64d43dcf763f0 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-000i-9400000000-e3995acc4818a98d0f48 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-0f79-9720000000-5d89487273e44ea61a68 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9700000000-209c737dcac7df2b198c | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0f79-5920000000-759a2f01b4f52767ade2 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9500000000-ff936b879a69b5d118f8 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-8920000000-e37b37d64d43dcf763f0 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9400000000-e3995acc4818a98d0f48 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0f79-9720000000-5d89487273e44ea61a68 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-7900000000-7e325567183fb56996d5 | Spectrum | GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0ufr-0930000000-be90b06add7135b4a539 | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dl-9000000000-52f9d8fc8386e4c512fe | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-9600000000-52aefdc997dac92c8459 | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methyl-2-oxobutanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-10ab58a33e9ca7dbace0 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9000000000-ad51ff01c94b6046ad64 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-9993174a7b1801b90ddb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00xr-9500000000-293818b81e0879b6feb2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9000000000-75058f27a2178b9cf121 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-4c20af39e8ee009d5278 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-9993174a7b1801b90ddb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00xr-9500000000-1a58c6a6b4f5477dabdd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-75058f27a2178b9cf121 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-cc4465a47e663be66df5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-00di-9100000000-19511890852fce513a02 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00kf-9300000000-30d3bdfb6d38dbb8e101 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-000l-9000000000-879b6502ff380673b776 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0159-9800000000-0cf4d3a0e7b3356995c6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-014o-9900000000-f35430a2eaea0d81df32 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00r2-9400000000-21f8c3fae79161c82099 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-9000000000-5f25e41413738bb6b5d7 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-801af00dea93fcfd637d | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01b9-8900000000-5185c7dfc72c25069904 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00xs-9200000000-7e2a275a65197f96f5d7 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0600-9000000000-0013e0ff06f9896a1337 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01b9-6900000000-7f00871b074cbd9a42e6 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06di-9400000000-6d56778068e11e4f8e85 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-b445e7fc67a8ff2bd3ba | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-9000000000-733fb7227d2d053b112f | 2021-09-25 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 48 |
---|
ChEMBL ID | CHEMBL146554 |
---|
KEGG Compound ID | C00141 |
---|
Pubchem Compound ID | 49 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 16530 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB04074 |
---|
HMDB ID | HMDB00019 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | HFL26-U:HFL26-U |
---|
EAFUS ID | 2433 |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | 34011 |
---|
KNApSAcK ID | C00007623 |
---|
HET ID | KIV |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | rw1047091 |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Branched-chain-amino-acid aminotransferase, cytosolic | BCAT1 | P54687 | Branched-chain-amino-acid aminotransferase, mitochondrial | BCAT2 | O15382 | Pyruvate dehydrogenase E1 component subunit beta, mitochondrial | PDHB | P11177 | Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial | PDHA1 | P08559 | Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial | PDHA2 | P29803 | 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial | BCKDHB | P21953 | Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial | DLAT | P10515 |
|
---|
Pathways | Name | SMPDB Link | KEGG Link |
---|
Valine, Leucine and Isoleucine Degradation | SMP00032 | map00280 |
|
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
fruity |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
|
|
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|