Record Information |
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Version | 1.0 |
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Created at | 2023-08-16 00:00:29 UTC |
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Updated at | 2024-04-19 09:50:52 UTC |
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NP-MRD ID | NP0331767 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | p-hydroxybenzaldehyde |
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Description | 4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. Outside of the human body, 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within a few different foods, such as vinegars, oats, and beers. 4-Hydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as peppers, sago palms, hazelnuts, sea-buckthornberries, and macadamia nut (m. Tetraphylla). It was first documented in 1975 (PMID: 1180912). This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods (PMID: 22770225) (PMID: 21542597) (PMID: 3593236). |
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Structure | InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H |
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Synonyms | Value | Source |
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4-Formylphenol | ChEBI | p-Formylphenol | ChEBI | p-Hydroxybenzaldehyde | ChEBI | 4-Hydroxy-benzaldehyde | HMDB | 4-Hydroxybenzenecarbonal | HMDB | p-Hydroxy-benzaldehyde | HMDB | p-Oxybenzaldehyde | HMDB | Parahydroxybenzaldehyde | HMDB | Usaf m-6 | HMDB | Para-hydroxybenzaldehyde | HMDB | 4-Hydroxybenzaldehyde | PhytoBank |
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Chemical Formula | C7H6O2 |
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Average Mass | 122.1213 Da |
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Monoisotopic Mass | 122.03678 Da |
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IUPAC Name | 4-hydroxybenzaldehyde |
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Traditional Name | P-hydroxybenzaldehyde |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC=C(C=O)C=C1 |
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InChI Identifier | InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H |
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InChI Key | RGHHSNMVTDWUBI-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-08-16 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-08-16 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl 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 | Hydroxybenzaldehydes |
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Alternative Parents | |
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Substituents | - Hydroxybenzaldehyde
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
- Hext PM, Rose FA: The Sulphation of p-hydroxyphenylpyruvic acid and related compounds by the rat liver cytosol. Biochem J. 1975 Aug;150(2):175-81. [PubMed:1180912 ]
- Wu MC, Peng CF, Chen IS, Tsai IL: Antitubercular chromones and flavonoids from Pisonia aculeata. J Nat Prod. 2011 May 27;74(5):976-82. doi: 10.1021/np1008575. Epub 2011 May 4. [PubMed:21542597 ]
- Sirimanne SR, Herman HH, May SW: Interaction of dopamine beta-mono-oxygenase with substituted imidazoles and pyrazoles. Catalysis and inhibition. Biochem J. 1987 Feb 15;242(1):227-33. doi: 10.1042/bj2420227. [PubMed:3593236 ]
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