| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2006-08-12 23:25:38 UTC |
|---|
| Updated at | 2021-10-07 20:41:03 UTC |
|---|
| NP-MRD ID | NP0000662 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Butanal |
|---|
| 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 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 cow milk 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 → CH3CH2CH2CHO. Traditionally, 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. |
|---|
| Structure | InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 |
|---|
| Synonyms | | Value | Source |
|---|
| 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 |
|
|---|
| Chemical Formula | C4H8O |
|---|
| Average Mass | 72.1057 Da |
|---|
| Monoisotopic Mass | 72.05751 Da |
|---|
| IUPAC Name | butanal |
|---|
| Traditional Name | butoxide |
|---|
| CAS Registry Number | 123-72-8 |
|---|
| SMILES | CCCC=O |
|---|
| InChI Identifier | InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 |
|---|
| InChI Key | ZTQSAGDEMFDKMZ-UHFFFAOYSA-N |
|---|
| Experimental Spectra |
|---|
|
| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
|---|
|
| Not Available | | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic oxygen compounds |
|---|
| Class | Organooxygen compounds |
|---|
| Sub Class | Carbonyl compounds |
|---|
| Direct Parent | Alpha-hydrogen aldehydes |
|---|
| Alternative Parents | |
|---|
| Substituents | - Alpha-hydrogen aldehyde
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | -99 °C | Not Available | | Boiling Point | 74.00 to 75.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | | Water Solubility | 71 mg/mL at 25 °C | Not Available | | LogP | 0.88 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
|
|---|
| Predicted Properties | |
|---|
| General References | - Orhan H, van Holland B, Krab B, Moeken J, Vermeulen NP, Hollander P, Meerman JH: Evaluation of a multi-parameter biomarker set for oxidative damage in man: increased urinary excretion of lipid, protein and DNA oxidation products after one hour of exercise. Free Radic Res. 2004 Dec;38(12):1269-79. [PubMed:15763951 ]
- Holley AE, Walker MK, Cheeseman KH, Slater TF: Measurement of n-alkanals and hydroxyalkenals in biological samples. Free Radic Biol Med. 1993 Sep;15(3):281-9. [PubMed:8406128 ]
- Rogers P, Palosaari N: Clostridium acetobutylicum Mutants That Produce Butyraldehyde and Altered Quantities of Solvents. Appl Environ Microbiol. 1987 Dec;53(12):2761-6. doi: 10.1128/aem.53.12.2761-2766.1987. [PubMed:16347493 ]
- Agirre I, Barrio VL, Guemez B, Cambra JF, Arias PL: Catalytic reactive distillation process development for 1,1 diethoxy butane production from renewable sources. Bioresour Technol. 2011 Jan;102(2):1289-97. doi: 10.1016/j.biortech.2010.08.064. Epub 2010 Aug 26. [PubMed:20833537 ]
- Cardinali F, Ferrocino I, Milanovic V, Belleggia L, Corvaglia MR, Garofalo C, Foligni R, Mannozzi C, Mozzon M, Cocolin L, Osimani A, Aquilanti L: Microbial communities and volatile profile of Queijo de Azeitao PDO cheese, a traditional Mediterranean thistle-curdled cheese from Portugal. Food Res Int. 2021 Sep;147:110537. doi: 10.1016/j.foodres.2021.110537. Epub 2021 Jun 17. [PubMed:34399514 ]
- Tourlakis GM, Adamopoulos SAT, Gavra IK, Milpanis AA, Tsagri LF, Pachygianni ASG, Chatzikokolis SS, Tsekouras AA: Sign flipping of spontaneous polarization in vapour-deposited films of small polar organic molecules. Phys Chem Chem Phys. 2021 Jul 7;23(26):14352-14362. doi: 10.1039/d1cp01584b. [PubMed:34169950 ]
- Weber S, Veiros LF, Kirchner K: Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes. ACS Catal. 2021 Jun 4;11(11):6474-6483. doi: 10.1021/acscatal.1c01137. Epub 2021 May 18. [PubMed:34123484 ]
|
|---|
