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{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 414648903 | verifiedrevid = 470619128
| ImageFile = tyrosol.png | ImageFile = Tyrosol.svg
| ImageSize = | ImageSize =
| IUPACName = 4-(2-Hydroxyethyl)phenol | PIN = 4-(2-Hydroxyethyl)phenol
| OtherNames = p-Hydroxyphenethyl alcohol<br />2-(4-Hydroxyphenyl)ethanol<br />4-Hydroxyphenylethanol | OtherNames = ''p''-Hydroxyphenethyl alcohol<br />2-(4-Hydroxyphenyl)ethanol<br />4-Hydroxyphenylethanol
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 | InChI = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
| InChIKey1 = YCCILVSKPBXVIP-UHFFFAOYSA-N | InChIKey1 = YCCILVSKPBXVIP-UHFFFAOYSA-N
| InChI1 = 1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2 | 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_Ref = {{cascite|correct|CAS}}
| CASNo = 501-94-0 | CASNo = 501-94-0
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 10393
| UNII = 1AK4MU3SNX
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PubChem = 10393
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9964 | ChemSpiderID = 9964
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1879 | ChEBI = 1879
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YCCILVSKPBXVIP-UHFFFAOYSA-N | StdInChIKey = YCCILVSKPBXVIP-UHFFFAOYSA-N
| SMILES = Oc1ccc(cc1)CCO | SMILES = Oc1ccc(cc1)CCO
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 53566 | ChEMBL = 53566
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | StdInChI =1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub> | Formula = C<sub>8</sub>H<sub>10</sub>O<sub>2</sub>
| MolarMass = 138.164 g/mol | MolarMass = 138.164 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPtC = 91 to 92
| MeltingPt = 91–92 °C
| MeltingPt_notes =
| BoilingPt = 158 °C at 4 Torr
| BoilingPtC = 158
⚫ | Solubility =
| BoilingPt_notes = at 4 Torr
⚫ }}
⚫ | Solubility =
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''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>
'''Tyrosol''' is a ]ic ] present in a variety of natural sources. The principal source in the human diet is ]. Tyrosol is a derivative of ]


== Research ==
As an antioxidant, tyrosol can protect cells against injury due to oxidation.<ref>{{cite journal |author=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}}</ref> Although it is not as potent as other antioxidants present in olive oil, its higher concentration and good ] indicate that it may have an important overall effect.<ref>{{cite journal |author=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}}</ref> This effect may contribute significantly to the health benefits of olive oil and, more generally, the ]. 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>


Recently Tyrosol present in white wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosol's SIRT1, Akt and eNOS activating power adds another dimension to the white wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart.<ref>{{cite journal |author=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=J.Agric. Food. Chem | year=2008.|pmid= 18826227 |volume=56 |issue=20 |pages=9692–8 |doi=10.1021/jf802050h |pmc=2648870}}</ref> 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>


In olive oil, tyrosol forms esters with fatty acids<ref>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. Ricardo Lucas, Francisco Comelles, David Alcntara, Olivia S. Maldonado, Melanie Curcuroze, Jose L. Parra and Juan C. Morales, J. Agric. Food Chem., 2010, 58 (13), pp 8021–8026, {{doi|10.1021/jf1009928}}</ref>. 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.


== See also == == See also ==
* ], {{chem2|HOC6H4CH2CH(NH2)CH2OH}}
* ] * ], {{chem2|(HO)2C6H3CH2CH2OH}}
* ]
* ], a glucoside of tyrosol


== References == == References ==
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{{Antioxidants}} {{Antioxidants}}


] ]
] ]
]

]
]

Latest revision as of 14:33, 24 November 2024

Tyrosol
Names
Preferred IUPAC name 4-(2-Hydroxyethyl)phenol
Other names p-Hydroxyphenethyl alcohol
2-(4-Hydroxyphenyl)ethanol
4-Hydroxyphenylethanol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.210 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2Key: YCCILVSKPBXVIP-UHFFFAOYSA-N
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
  • InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2Key: YCCILVSKPBXVIP-UHFFFAOYSA-N
SMILES
  • Oc1ccc(cc1)CCO
Properties
Chemical formula C8H10O2
Molar mass 138.164 g/mol
Melting point 91 to 92 °C (196 to 198 °F; 364 to 365 K)
Boiling point 158 °C (316 °F; 431 K) at 4 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Tyrosol is an organic compound with the formula 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.

Research

As an antioxidant, tyrosol may protect cells against injury due to oxidation in vitro. 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.

Tyrosol may also be cardioprotective. Tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS, and FOXO3a. In addition, tyrosol also induced the expression of the protein SIRT1 in the heart after myocardial infarction (MI) in a rat MI model.

Tyrosol forms esters with a variety of organic acids. For example, oleocanthal is the elenolic acid ester of tyrosol.

See also

References

  1. Charoenprasert, Suthawan; Mitchell, Alyson (2012). "Factors Influencing Phenolic Compounds in Table Olives (Olea europaea)". Journal of Agricultural and Food Chemistry. 60 (29): 7081–7095. doi:10.1021/jf3017699. PMID 22720792.
  2. Karković Marković, Ana; Torić, Jelena; Barbarić, Monika; Jakobušić Brala, Cvijeta (2019). "Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health". Molecules. 24 (10): 2001. doi:10.3390/molecules24102001. PMC 6571782. PMID 31137753.
  3. Giovannini C, Straface E, Modesti D, Coni E, Cantafora A, De Vincenzi M, Malorni W, Masella R (1999). "Tyrosol, the major olive oil biophenol, protects against oxidized-LDL-induced injury in Caco-2 cells". J. Nutr. 129 (7): 1269–1277. doi:10.1093/jn/129.7.1269. PMID 10395586.
  4. Miró-Casas E, Covas M, Fitó M, Farré-Albadalejo M, Marrugat J, de la Torre R (2003). "Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans". European Journal of Clinical Nutrition. 57 (1): 186–190. doi:10.1038/sj.ejcn.1601532. PMID 12548315.
  5. Samuel SM, Thirunavukkarasu M, Penumathsa SV, Paul D, Maulik N (2008). "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 of Agricultural and Food Chemistry. 56 (20): 9692–8. doi:10.1021/jf802050h. PMC 2648870. PMID 18826227.
  6. Samuel, Samson Mathews; Thirunavukkarasu, Mahesh; Penumathsa, Suresh Varma; Paul, Debayon; Maulik, Nilanjana (2008-10-22). "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 of Agricultural and Food Chemistry. 56 (20): 9692–9698. doi:10.1021/jf802050h. ISSN 1520-5118. PMC 2648870. PMID 18826227.
  7. Lucas, Ricardo; Comelles, Francisco; AlcáNtara, David; Maldonado, Olivia S.; Curcuroze, Melanie; Parra, Jose L.; Morales, Juan C. (2010). "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 of Agricultural and Food Chemistry. 58 (13): 8021–8026. doi:10.1021/jf1009928. PMID 20524658.
Antioxidants
Food antioxidants
Fuel antioxidants
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