Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:46 UTC |
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Update date | 2020-09-17 15:39:14 UTC |
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Primary ID | FDB003378 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Butanal |
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Description | Butanal, also known as butyral or butyl aldehyde, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. It is miscible with most organic solvents. Butanal is an extremely weak basic (essentially neutral) compound (based on its pKa). Butanal exists in all living organisms, ranging from bacteria to humans. Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid. Butanal is an apple, bready, and chocolate tasting compound. Outside of the human body, Butanal is found, on average, in the highest concentration within milk (cow) and carrots. Butanal has also been detected, but not quantified in, several different foods, such as hard wheats, borages, ostrich ferns, skunk currants, and fennels. This could make butanal a potential biomarker for the consumption of these foods. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand Tppts. Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:CH3CHCH2 + H2 + CO → CH3CH2CH2CHOTraditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. This compound is the aldehyde derivative of butane. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. It is a colourless flammable liquid with an unpleasant smell. |
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CAS Number | 123-72-8 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Butanal | ChEBI | Aldehyde butyrique | ChEBI | Aldeide butirrica | ChEBI | Butal | ChEBI | Butaldehyde | ChEBI | Butan-1-al | ChEBI | Butanaldehyde | ChEBI | Butyl aldehyde | ChEBI | Butylaldehyde | ChEBI | Butyral | ChEBI | Butyraldehyd | ChEBI | Butyraldehyde | ChEBI | Butyric aldehyde | ChEBI | Butyrylaldehyde | ChEBI | N-Butanal | ChEBI | N-Butyl aldehyde | ChEBI | N-Butyraldehyde | ChEBI | N-C3H7CHO | ChEBI | Butalyde | HMDB | N-Butylaldehyde | HMDB | butan-1-al | biospider | Butanal n-butyraldehyde | biospider | Butyraldehyd(german) | biospider | Butyraldehyde (crude) | biospider | Butyraldehyde [UN1129] [Flammable liquid] | biospider | Butyraldehyde, 8CI | db_source | FEMA 2219 | db_source | N-butanal | biospider | N-butyl aldehyde | biospider | N-butylaldehyde | biospider | N-butyraldehyde | biospider | n-C3H7CHO | biospider |
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Predicted Properties | |
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Chemical Formula | C4H8O |
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IUPAC name | butanal |
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InChI Identifier | InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 |
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InChI Key | ZTQSAGDEMFDKMZ-UHFFFAOYSA-N |
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Isomeric SMILES | CCCC=O |
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Average Molecular Weight | 72.1057 |
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Monoisotopic Molecular Weight | 72.057514878 |
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Classification |
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Description | Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Alpha-hydrogen aldehydes |
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Alternative Parents | |
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Substituents | - Alpha-hydrogen aldehyde
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- 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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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 66.63%; H 11.18%; O 22.19% | DFC |
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Melting Point | Fp -99° | DFC |
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Boiling Point | Bp 75° | DFC |
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Experimental Water Solubility | 71 mg/mL at 25 oC | UNION CARBIDE (1974) |
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Experimental logP | 0.88 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d25 0.8 | DFC |
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Refractive Index | n20D 1.3790 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-002f-9000000000-6e0649a0dc70c28fcae9 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-002f-9000000000-98b59bf5bd3eda9e49fa | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-68ac34ab9def2e36ccc6 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-2900000000-6dd687b5afd856171273 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-1900000000-d64b8c5293749714544a | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-2900000000-33689f43c983a22378e7 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-002f-9000000000-98b59bf5bd3eda9e49fa | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-68ac34ab9def2e36ccc6 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-2900000000-6dd687b5afd856171273 | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-1900000000-d64b8c5293749714544a | Spectrum | GC-MS | Butanal, non-derivatized, GC-MS Spectrum | splash10-0002-2900000000-33689f43c983a22378e7 | Spectrum | Predicted GC-MS | Butanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-9000000000-4fb49b6897fd6c8e92b4 | Spectrum | Predicted GC-MS | Butanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0ab9-9000000000-e43f72b51db74df7e649 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-052f-9000000000-038773fb1932929717e0 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000x-9000000000-f3c990a0bfba019420a9 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-002f-9000000000-c275231e3f5b37fbd589 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-0006-9000000000-68ac34ab9def2e36ccc6 | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-f9de404f1affa6abfa9a | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-05fr-9000000000-cfe5c3be3e144243331c | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0005-9000000000-1edcf9e61e3340fbf40d | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-052e-9000000000-bccfaaf4b9811638acfe | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-05fr-9000000000-c4d921bc1daac3882310 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-2c1d033322fd9522a728 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-9000000000-ca73d37ef37b38522b6e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-90b6f84d1349c54881ce | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-819efd4b2a60ead6a85c | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-59b84d540828a6511e53 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-f665ffadd808f7e9b0ca | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-9000000000-a41fb6d601c30ec7f891 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-cb39b818de83422d81fb | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4u-9000000000-6df66caca042bdf0c409 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-77e5dcf17bd83eca2c67 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-0a10c7980c8eb7716de6 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-50a44f96027b04e2ca63 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 256 |
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ChEMBL ID | CHEMBL1478334 |
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KEGG Compound ID | C01412 |
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Pubchem Compound ID | 261 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03543 |
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CRC / DFC (Dictionary of Food Compounds) ID | CXB54-W:CXB54-W |
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EAFUS ID | 436 |
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Dr. Duke ID | N-BUTYRALDEHYDE|BUTYRALDEHYDE|BUTANAL |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 123-72-8 |
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GoodScent ID | rw1007681 |
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SuperScent ID | 261 |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | irritant | | | DUKE | narcotic | 35482 | A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Retinol dehydrogenase 13 | RDH13 | Q8NBN7 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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pungent |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| green |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| vegetable |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| herbaceous |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| creamy |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| fatty |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| spicy |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| floral |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| chocolate |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| citrus |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| woody |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| meaty |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| wine_like |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| earthy |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| apple |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| fruity |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| pear |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| nutty |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| cocoa |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| musty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| malty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bready |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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