Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:45 UTC |
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Update date | 2020-09-17 15:35:40 UTC |
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Primary ID | FDB000893 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Phenol |
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Description | Phenol, also known as hydroxybenzene or carbolic acid, belongs to the class of organic compounds known as hydroxy benzenoids. Phenol is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of microorganisms including some fungi and viruses but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe. In laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). |
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CAS Number | 108-95-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Acide carbolique | ChEBI | Acide phenique | ChEBI | Benzenol | ChEBI | Carbolic acid | ChEBI | Carbolsaeure | ChEBI | Hydroxybenzene | ChEBI | Karbolsaeure | ChEBI | Oxybenzene | ChEBI | Phenic acid | ChEBI | Phenylic acid | ChEBI | Phenylic alcohol | ChEBI | PHOH | ChEBI | Liquefied phenol | Kegg | Phenol for disinfection | Kegg | Phenol, liquefied | Kegg | Paoscle | Kegg | Carbolate | Generator | Phenate | Generator | Phenylate | Generator | Anbesol | HMDB | Benzophenol | HMDB | Campho-phenique cold sore gel | HMDB | Campho-phenique gel | HMDB | Campho-phenique liquid | HMDB | Carbolic acid liquid | HMDB | Carbolic oil | HMDB | Carbolicum acidum | HMDB | Carbolsaure | HMDB | Cepastat lozenges | HMDB | Cuticura pain relieving ointment | HMDB | Fenol | HMDB | Fenolo | HMDB | Fenosmolin | HMDB | Fenosmoline | HMDB | Hydroxy-benzene | HMDB | IPH | HMDB | IZAL | HMDB | Liquid phenol | HMDB | Liquified phenol | HMDB | Monohydroxy benzene | HMDB | Monohydroxybenzene | HMDB | Monophenol | HMDB | Phenic | HMDB | Phenic alcohol | HMDB | Phenol alcohol | HMDB | Phenol homopolymer | HMDB | Phenol liquid | HMDB | Phenol molten | HMDB | Phenol polymer-bound | HMDB | Phenol solution | HMDB | Phenol synthetic | HMDB | Phenolated water | HMDB | Phenolated water for disinfection | HMDB | Phenole | HMDB | Phenosmolin | HMDB | Synthetic phenol | HMDB | Tea polyphenol | HMDB | Phenol, sodium salt | HMDB | Phenolate sodium | HMDB | Carbol | HMDB | Phenolate, sodium | HMDB | Sodium phenolate | HMDB | FEMA 3223 | db_source | Phenyl alcohol | manual | Phenyl hydrate | manual | Phenyl hydroxide | manual |
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Predicted Properties | |
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Chemical Formula | C6H6O |
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IUPAC name | phenol |
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InChI Identifier | InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H |
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InChI Key | ISWSIDIOOBJBQZ-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=CC=C1 |
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Average Molecular Weight | 94.1112 |
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Monoisotopic Molecular Weight | 94.041864814 |
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Classification |
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Description | Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | 1-hydroxy-4-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-4-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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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Physiological effect | Health effect: |
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Disposition | Source: Route of exposure: Biological location: |
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Role | Environmental role: Industrial application: |
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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 76.57%; H 6.43%; O 17.00% | DFC |
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Melting Point | Fp 41° | DFC |
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Boiling Point | Bp25 90.2° | DFC |
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Experimental Water Solubility | 82.8 mg/mL at 25 oC | SOUTHWORTH,GR & KELLER,JL (1986) |
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Experimental logP | 1.46 | 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 | 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) | splash10-00kf-9000000000-40b376f4e58c23369a01 | 2014-09-20 | View Spectrum | GC-MS | Phenol, 1 TMS, GC-MS Spectrum | splash10-0udi-3900000000-97dfa3be718a9ee7ace4 | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-00kf-9000000000-6fb456992902a13931f9 | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-78c83ab6ff1d3dfdbec6 | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-89b0c430b8924ee2afde | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-fc01d0ad6740cfd70e13 | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-006w-9000000000-c8b41f2899ca8cc9d4bc | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-db80d8b605e20595c679 | Spectrum | GC-MS | Phenol, non-derivatized, GC-MS Spectrum | splash10-0udi-3900000000-97dfa3be718a9ee7ace4 | Spectrum | Predicted GC-MS | Phenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-c35c89484e2499c62a49 | Spectrum | Predicted GC-MS | Phenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0g4i-9300000000-afd565a878ea36c74def | Spectrum | Predicted GC-MS | Phenol, 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, Negative (Annotated) | splash10-0006-9000000000-e67da0571423f0e6b4b8 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0006-9000000000-e0f57b1e970d0d46597e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0006-9000000000-e67da0571423f0e6b4b8 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-00kf-9000000000-7bfe3b897e928a8f3a2c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive | splash10-0006-9000000000-78c83ab6ff1d3dfdbec6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0006-9000000000-89b0c430b8924ee2afde | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0006-9000000000-fc01d0ad6740cfd70e13 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-0006-9000000000-ca4fa5905cccbfeab33a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-e3e33defb000b450bb37 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9200000000-d63db79771e5931b258f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-448a4d79ff53d77a8b16 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-2c7201e803e029dd1aef | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-3fb3990dfbfbde2b8d57 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gba-9000000000-d3da8db6579f32d02c6c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-a74494cda18ab9fb8055 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-a74494cda18ab9fb8055 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-03a61ff7da92cb08edf8 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-c65d4a4eaa8adde2ddb4 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-9000000000-def7a8d52afb63a3cd67 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-f3c795ffc788635ddbf4 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-08485aaf085c13d5129a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-08485aaf085c13d5129a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-52b0f93832ef13f17bd2 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 971 |
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ChEMBL ID | CHEMBL14060 |
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KEGG Compound ID | C15584 |
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Pubchem Compound ID | 996 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15882 |
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Phenol-Explorer ID | 657 |
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DrugBank ID | DB03255 |
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HMDB ID | HMDB00228 |
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CRC / DFC (Dictionary of Food Compounds) ID | BLS38-K:BLS38-K |
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EAFUS ID | 2977 |
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Dr. Duke ID | PHENOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002664 |
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HET ID | IPH |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 108-95-2 |
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GoodScent ID | rw1009361 |
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SuperScent ID | Not Available |
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Wikipedia ID | Phenol |
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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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analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anesthetic | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti hemorrhoidal | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti hydrocoele | | | DUKE | anti incontinence | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti monosodium-glutamate | | | DUKE | anti onychogryphotic | | | DUKE | anti otitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti prostatitic | | | DUKE | anti pyruvetic | | | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti sinusitic | | | DUKE | anti spastic | | | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti wrinkle | | | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | emetic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hemolytic | | | 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 | rodenticide | 33288 | A substance used to destroy rodent pests. | DUKE | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Serum paraoxonase/lactonase 3 | PON3 | Q15166 | Serum paraoxonase/arylesterase 1 | PON1 | P27169 | Serum paraoxonase/arylesterase 2 | PON2 | Q15165 | 6-phosphogluconolactonase | PGLS | O95336 | Glucose-6-phosphate 1-dehydrogenase | G6PD | P11413 | Sulfotransferase 1A1 | SULT1A1 | P50225 | Sulfotransferase 1A2 | SULT1A2 | P50226 | Sulfotransferase 1A3/1A4 | SULT1A3 | P50224 | 6-phosphogluconate dehydrogenase, decarboxylating | PGD | P52209 |
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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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phenol |
- 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
| phenolic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| plastic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| rubber |
- 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). — 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. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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