Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:09 UTC |
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Update date | 2019-11-26 03:03:39 UTC |
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Primary ID | FDB010504 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-Hydroxybenzaldehyde |
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Description | Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum)
4-Hydroxybenzaldehyde reacts with NAD+ and H2O to produce 4-hydroxybenzoate, NADH, and 2 protons. The reaction is catalyzed by 4-hydroxybenzaldehyde dehydrogenase.; ; 4-Hydroxybenzaldehyde is found in the benzoate degradation via hydroxylation, bisphenol A degradation, toluene and xylene degradation, and biosynthesis of phenylpropanoids pathways. |
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CAS Number | 123-08-0 |
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Structure | |
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Synonyms | Synonym | 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 | 4-hydroxy-Benzaldehyde | biospider | 4-Hydroxybenzaldehyde, homopolymer | biospider | Benzaldehyde, 4-hydroxy- | biospider | Benzaldehyde, 4-hydroxy-, homopolymer | biospider | Benzaldehyde, p-hydroxy- | biospider | HBA | biospider | P-Hydroxy-benzaldehyde | HMDB | P-hydroxybenzaldehyde | biospider | P-oxybenzaldehyde | biospider | P-oxybenzaldehyde;p-hydroxy-benzaldehyde | biospider | PHB | biospider |
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Predicted Properties | |
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Chemical Formula | C7H6O2 |
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IUPAC name | 4-hydroxybenzaldehyde |
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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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Isomeric SMILES | OC1=CC=C(C=O)C=C1 |
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Average Molecular Weight | 122.1213 |
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Monoisotopic Molecular Weight | 122.036779436 |
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Classification |
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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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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 68.85%; H 4.95%; O 26.20% | DFC |
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Melting Point | Mp 115-116° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 8.45 mg/mL at 25 oC | JIN,LJ et al. (1998) |
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Experimental logP | 1.35 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 7.62 (25°, H2O) | DFC |
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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 | 330 (e 6600) (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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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) | splash10-00di-9500000000-2c1739a8a2bc288e4a5c | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-4eff34096f6bd4f30d10 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-9800000000-c8646d08ef8e23a3d49b | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-60621d4d9871b2d7587d | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-05i0-1970000000-7ef151eab685361413a6 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-1940000000-fa6b812457f26dce7720 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2940000000-b50ed8954cb10b92a30b | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2930000000-671031e52722de3402ec | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-4eff34096f6bd4f30d10 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-9800000000-c8646d08ef8e23a3d49b | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00di-8900000000-60621d4d9871b2d7587d | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-05i0-1970000000-7ef151eab685361413a6 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-1940000000-fa6b812457f26dce7720 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2 | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2940000000-b50ed8954cb10b92a30b | Spectrum | GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum | splash10-00b9-2930000000-671031e52722de3402ec | Spectrum | Predicted GC-MS | 4-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-6900000000-ea309e8826550692ddeb | Spectrum | Predicted GC-MS | 4-Hydroxybenzaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-8900000000-781df730e85ee6b33891 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-00di-0900000000-99136b39c7ec11a7bbca | Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-00di-0900000000-ab4c213ba9a645517aa3 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0002-9300000000-7a1d8d268b763ce71331 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-002g-9000000000-e9050639f16e3b6d7939 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-00di-0900000000-27effb3a35bdb0d72310 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-00di-1900000000-731f917249c17a761e0f | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-00dj-5900000000-c46a92738e14de26b66c | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-006t-9500000000-7f1f8c64931b0dc6f66f | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0002-9100000000-39037b9523c5f3c7ed6c | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-0002-9000000000-06c809ed4b25327e8b09 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-002b-9000000000-b93cdaad48fe246028dd | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-002b-9000000000-16e7fae11656d4e6cd8a | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 7V, positive | splash10-0fba-9000000000-96924ab5b95b0d4fb857 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-298ab6a83ac989405983 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-12ad1640340af91bc8e8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0036-9000000000-ddc48e682b255bd53c5e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-785058db9c1fbc1b5950 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-c22365c838c065b99ed8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0100-9300000000-491fc6287b2479ddc1a6 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-298ab6a83ac989405983 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-12ad1640340af91bc8e8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0036-9000000000-ddc48e682b255bd53c5e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-785058db9c1fbc1b5950 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-c22365c838c065b99ed8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0100-9300000000-491fc6287b2479ddc1a6 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 123 |
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ChEMBL ID | CHEMBL14193 |
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KEGG Compound ID | C00633 |
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Pubchem Compound ID | 126 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 725 |
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DrugBank ID | DB03560 |
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HMDB ID | HMDB11718 |
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CRC / DFC (Dictionary of Food Compounds) ID | FBR96-V:FBR96-V |
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EAFUS ID | 1724 |
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Dr. Duke ID | 4-HYDROXYBENZALDEHYDE|P-HYDROXYBENZALDEHYDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002657 |
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HET ID | HBA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1040191 |
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SuperScent ID | Not Available |
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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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allelochemic | | | DUKE | anti feedant | | | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | tyrosinase inhibitor | 59997 | Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. | DUKE |
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Enzymes | Not Available |
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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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sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| nutty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| almond |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| balsam |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- 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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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