| Revision as of 14:39, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463827807 of page Tyrosol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:33, 24 November 2024 edit Reba16 (talk | contribs)Extended confirmed users8,067 editsNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 414648903 |
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| verifiedrevid = 470619128 |
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| ImageFile = tyrosol.png |
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| ImageFile = Tyrosol.svg |
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| ImageSize = |
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| ImageSize = |
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| IUPACName = 4-(2-Hydroxyethyl)phenol |
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| PIN = 4-(2-Hydroxyethyl)phenol |
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| OtherNames = p-Hydroxyphenethyl alcohol<br />2-(4-Hydroxyphenyl)ethanol<br />4-Hydroxyphenylethanol |
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| OtherNames = ''p''-Hydroxyphenethyl alcohol<br />2-(4-Hydroxyphenyl)ethanol<br />4-Hydroxyphenylethanol |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| 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 = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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| InChIKey1 = YCCILVSKPBXVIP-UHFFFAOYSA-N |
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| InChIKey1 = YCCILVSKPBXVIP-UHFFFAOYSA-N |
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| InChI1 = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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| InChI1 = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 501-94-0 |
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| CASNo = 501-94-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 10393 |
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| UNII = 1AK4MU3SNX |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 10393 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9964 |
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| ChemSpiderID = 9964 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 1879 |
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| ChEBI = 1879 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YCCILVSKPBXVIP-UHFFFAOYSA-N |
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| StdInChIKey = YCCILVSKPBXVIP-UHFFFAOYSA-N |
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| SMILES = Oc1ccc(cc1)CCO |
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| SMILES = Oc1ccc(cc1)CCO |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 53566 |
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| ChEMBL = 53566 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI =1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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| StdInChI =1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub> |
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| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub> |
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| MolarMass = 138.164 g/mol |
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| MolarMass = 138.164 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPtC = 91 to 92 |
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| MeltingPt = 91–92 °C |
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| MeltingPt_notes = |
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| BoilingPt = 158 °C at 4 Torr |
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| BoilingPtC = 158 |
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| Solubility = |
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| BoilingPt_notes = at 4 Torr |
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}} |
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| Solubility = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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}} |
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'''Tyrosol''' is an ] with the formula {{chem2|HOC6H4CH2CH2OH}}. Classified as a ], a derivative of ], it is found in a variety of natural sources. The compound is colorless solid. The principal source in the human diet is ].<ref>{{cite journal |doi=10.1021/jf3017699|title=Factors Influencing Phenolic Compounds in Table Olives (Olea europaea) |year=2012 |last1=Charoenprasert |first1=Suthawan |last2=Mitchell |first2=Alyson |journal=Journal of Agricultural and Food Chemistry |volume=60 |issue=29 |pages=7081–7095 |pmid=22720792 }}</ref><ref>{{cite journal |doi=10.3390/molecules24102001|doi-access=free |title=Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health |year=2019 |last1=Karković Marković |first1=Ana |last2=Torić |first2=Jelena |last3=Barbarić |first3=Monika |last4=Jakobušić Brala |first4=Cvijeta |journal=Molecules |volume=24 |issue=10 |page=2001 |pmid=31137753 |pmc=6571782 }}</ref> |
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== Research == |
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As an ], tyrosol may protect cells against injury due to oxidation '']''.<ref>{{cite journal |vauthors=Giovannini C, Straface E, Modesti D, Coni E, Cantafora A, De Vincenzi M, Malorni W, Masella R |title=Tyrosol, the major olive oil biophenol, protects against oxidized-LDL-induced injury in Caco-2 cells |journal=J. Nutr. |volume=129 |issue=7 |pages=1269–1277 |year=1999 |pmid=10395586|doi=10.1093/jn/129.7.1269 |doi-access=free }}</ref> Although it is not as potent as other antioxidants present in olive oil (e.g., ]), its higher concentration and good ] indicate that it may have an important overall effect.<ref>{{cite journal |vauthors=Miró-Casas E, Covas M, Fitó M, Farré-Albadalejo M, Marrugat J, de la Torre R |title=Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans |journal=European Journal of Clinical Nutrition |volume=57 |issue=1 |pages=186–190 |year=2003 |pmid=12548315 |doi=10.1038/sj.ejcn.1601532|doi-access=free }}</ref> |
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Tyrosol may also be cardioprotective. Tyrosol-treated animals showed significant increase in the phosphorylation of ], ], and ].<ref>{{cite journal |vauthors=Samuel SM, Thirunavukkarasu M, Penumathsa SV, Paul D, Maulik N |title= Akt/FOXO3a/SIRT1-Mediated Cardioprotection by n-Tyrosol against Ischemic Stress in Rat in Vivo Model of Myocardial Infarction: Switching Gears toward Survival and Longevity.|journal=] | year=2008|pmid= 18826227 |volume=56 |issue=20 |pages=9692–8 |doi=10.1021/jf802050h |pmc=2648870}}</ref> In addition, tyrosol also induced the expression of the protein ] in the heart after ] (MI) in a rat MI model.<ref>{{Cite journal|last1=Samuel|first1=Samson Mathews|last2=Thirunavukkarasu|first2=Mahesh|last3=Penumathsa|first3=Suresh Varma|last4=Paul|first4=Debayon|last5=Maulik|first5=Nilanjana|date=2008-10-22|title=Akt/FOXO3a/SIRT1-mediated cardioprotection by n-tyrosol against ischemic stress in rat in vivo model of myocardial infarction: switching gears toward survival and longevity|journal=Journal of Agricultural and Food Chemistry|volume=56|issue=20|pages=9692–9698|doi=10.1021/jf802050h|issn=1520-5118|pmc=2648870|pmid=18826227}}</ref> |
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Tyrosol forms esters with a variety of organic acids.<ref>{{Cite journal|last1=Lucas|first1=Ricardo|last2=Comelles|first2=Francisco|last3=AlcáNtara|first3=David|last4=Maldonado|first4=Olivia S.|last5=Curcuroze|first5=Melanie|last6=Parra|first6=Jose L.|last7=Morales|first7=Juan C.|year=2010|title=Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters: A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions|journal=Journal of Agricultural and Food Chemistry|volume=58|issue=13|pages=8021–8026|doi=10.1021/jf1009928|pmid=20524658}}</ref> For example, ] is the ] ester of tyrosol. |
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== See also == |
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* ], {{chem2|HOC6H4CH2CH(NH2)CH2OH}} |
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* ], {{chem2|(HO)2C6H3CH2CH2OH}} |
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* ], a glucoside of tyrosol |
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== References == |
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{{Reflist}} |
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{{Antioxidants}} |
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] |
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] |
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] |