Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 16:05:03 UTC |
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Update Date | 2023-02-21 17:16:59 UTC |
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HMDB ID | HMDB0004284 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tyrosol |
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Description | Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375 ). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285 ). |
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Structure | InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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Synonyms | Value | Source |
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4-Hydroxybenzeneethanol | ChEBI | 4-Hydroxyphenylethanol | ChEBI | p-Hydroxyphenethyl alcohol | ChEBI | 2-(4-Hydroxyphenyl)ethanol | HMDB | 2-(p-Hydroxyphenyl)ethanol | HMDB | 4-(2-Hydroxyethyl)phenol | HMDB | 4-Hydroxyphenethyl alcohol | HMDB | 4-Hydroxyphenylethyl alcohol | HMDB | b-(4-Hydroxyphenyl)ethanol | HMDB | b-(P-Hydroxyphenyl)ethanol | HMDB | beta-(4-Hydroxyphenyl)ethanol | HMDB, MeSH | beta-(p-Hydroxyphenyl)ethanol | HMDB | P-Hydroxyphenylethyl alcohol | HMDB | P-Thyrosol | HMDB | p-Tyrosol | HMDB, MeSH | Para-hydroxyphenylethanol | MeSH, HMDB | P-Hydroxyphenylethanol | MeSH, HMDB | N-Tyrosol | MeSH, HMDB | 2-(4-Hydroxyphenyl)ethyl alcohol | HMDB | Tyrosol | HMDB | p-(2-Hydroxyethyl)phenol | HMDB | p-HPEA | HMDB | β-(4-Hydroxyphenyl)ethanol | HMDB | β-(p-Hydroxyphenyl)ethanol | HMDB | 2-(3',4'-dihydroxyphenyl)ethanol | HMDB | 2-(4'-Hydroxyphenyl)ethanol | HMDB | 4-Hydroxyphenyl alcohol | HMDB |
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Chemical Formula | C8H10O2 |
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Average Molecular Weight | 138.1638 |
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Monoisotopic Molecular Weight | 138.068079564 |
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IUPAC Name | 4-(2-hydroxyethyl)phenol |
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Traditional Name | tyrosol |
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CAS Registry Number | 501-94-0 |
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SMILES | OCCC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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InChI Key | YCCILVSKPBXVIP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tyrosols. These are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. |
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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 | Tyrosols and derivatives |
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Direct Parent | Tyrosols |
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Alternative Parents | |
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Substituents | - Tyrosol
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- 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 | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Tyrosol,1TMS,isomer #1 | C[Si](C)(C)OCCC1=CC=C(O)C=C1 | 1554.9 | Semi standard non polar | 33892256 | Tyrosol,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(CCO)C=C1 | 1489.7 | Semi standard non polar | 33892256 | Tyrosol,2TMS,isomer #1 | C[Si](C)(C)OCCC1=CC=C(O[Si](C)(C)C)C=C1 | 1567.4 | Semi standard non polar | 33892256 | Tyrosol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CC=C(O)C=C1 | 1779.3 | Semi standard non polar | 33892256 | Tyrosol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCO)C=C1 | 1741.7 | Semi standard non polar | 33892256 | Tyrosol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 2028.4 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Tyrosol GC-MS (2 TMS) | splash10-004i-1920000000-4795e885578e89b76024 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tyrosol EI-B (Non-derivatized) | splash10-004i-0920000000-09ea62430af3397e5fbb | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tyrosol GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-b6e98d450debce3e52f5 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tyrosol GC-MS (Non-derivatized) | splash10-004i-1920000000-4795e885578e89b76024 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tyrosol GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-12207240533c46fdea75 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tyrosol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-5900000000-83585cd03b0a8c1b3067 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tyrosol GC-MS (2 TMS) - 70eV, Positive | splash10-00vi-9840000000-6d4093c692b4db8587ed | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tyrosol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 10V, Positive-QTOF | splash10-00dr-0900000000-49e061bee76cb42ff710 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 20V, Positive-QTOF | splash10-00di-1900000000-f0aacb9c7e251e486554 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 40V, Positive-QTOF | splash10-0fml-9400000000-8e06cbec5e72d3855569 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 10V, Negative-QTOF | splash10-000i-0900000000-b7c90f6632ed711d170c | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 20V, Negative-QTOF | splash10-0a4r-0900000000-676aa996456f5f0baa94 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 40V, Negative-QTOF | splash10-05mo-9800000000-6ea2f536e15d77c65310 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 10V, Negative-QTOF | splash10-000i-0900000000-752d6f7c286547d7e30b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 20V, Negative-QTOF | splash10-066r-0900000000-23b0337f09b1b4332c49 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 40V, Negative-QTOF | splash10-00kf-9600000000-d2607175df1bef897139 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 10V, Positive-QTOF | splash10-00di-3900000000-45201e48f40748120cd5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 20V, Positive-QTOF | splash10-00fu-9600000000-fc309e7875f3399eb472 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tyrosol 40V, Positive-QTOF | splash10-004l-9000000000-228e273810e98c38c9fc | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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General References | - Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
- Vissers MN, Zock PL, Roodenburg AJ, Leenen R, Katan MB: Olive oil phenols are absorbed in humans. J Nutr. 2002 Mar;132(3):409-17. [PubMed:11880564 ]
- Tsarbopoulos A, Gikas E, Papadopoulos N, Aligiannis N, Kafatos A: Simultaneous determination of oleuropein and its metabolites in plasma by high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):157-64. [PubMed:12535848 ]
- Miles EA, Zoubouli P, Calder PC: Differential anti-inflammatory effects of phenolic compounds from extra virgin olive oil identified in human whole blood cultures. Nutrition. 2005 Mar;21(3):389-94. [PubMed:15797683 ]
- Visioli F, Galli C, Bornet F, Mattei A, Patelli R, Galli G, Caruso D: Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000 Feb 25;468(2-3):159-60. [PubMed:10692578 ]
- Covas MI, Miro-Casas E, Fito M, Farre-Albadalejo M, Gimeno E, Marrugat J, De La Torre R: Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Drugs Exp Clin Res. 2003;29(5-6):203-6. [PubMed:15134375 ]
- Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
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