Tyrosol
{{chembox
| Watchedfields = changed
| verifiedrevid = 470619128
| ImageFile = Tyrosol.svg
| ImageSize =
| PIN = 4-(2-Hydroxyethyl)phenol
| OtherNames = p-Hydroxyphenethyl alcohol
2-(4-Hydroxyphenyl)ethanol
4-Hydroxyphenylethanol
|Section1={{Chembox Identifiers
| InChI = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
| InChIKey1 = YCCILVSKPBXVIP-UHFFFAOYSA-N
| InChI1 = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 501-94-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1AK4MU3SNX
| PubChem = 10393
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9964
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1879
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YCCILVSKPBXVIP-UHFFFAOYSA-N
| SMILES = Oc1ccc(cc1)CCO
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 53566
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
}}
|Section2={{Chembox Properties
| Formula = C8H10O2
| MolarMass = 138.164 g/mol
| Appearance =
| Density =
| MeltingPtC = 91 to 92
| MeltingPt_notes =
| BoilingPtC = 158
| BoilingPt_notes = at 4 Torr
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Tyrosol is an organic compound with the formula {{chem2|HOC6H4CH2CH2OH}}. Classified as a phenylethanoid, a derivative of phenethyl alcohol, it is found in a variety of natural sources. The compound is colorless solid. The principal source in the human diet is olive oil.{{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 }}{{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 }}
Research
As an antioxidant, tyrosol may protect cells against injury due to oxidation in vitro.{{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 }} Although it is not as potent as other antioxidants present in olive oil (e.g., hydroxytyrosol), its higher concentration and good bioavailability indicate that it may have an important overall effect.{{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 }}
Tyrosol may also be cardioprotective. Tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS, and FOXO3a.{{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=Journal of Agricultural and Food Chemistry | year=2008|pmid= 18826227 |volume=56 |issue=20 |pages=9692–8 |doi=10.1021/jf802050h |pmc=2648870}} In addition, tyrosol also induced the expression of the protein SIRT1 in the heart after myocardial infarction (MI) in a rat MI model.{{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}}
Tyrosol forms esters with a variety of organic acids.{{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}} For example, oleocanthal is the elenolic acid ester of tyrosol.
See also
- Tyrosinol, {{chem2|HOC6H4CH2CH(NH2)CH2OH}}
- Hydroxytyrosol, {{chem2|(HO)2C6H3CH2CH2OH}}
- Salidroside, a glucoside of tyrosol