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Showing NP-Card for Hydroxytyrosol (NP0047361)

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Record Information
Version2.0
Created at2022-03-17 20:38:55 UTC
Updated at2024-09-03 04:16:38 UTC
NP-MRD IDNP0047361
Natural Product DOIhttps://doi.org/10.57994/0743
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxytyrosol
DescriptionHydroxytyrosol, also known as dopet, 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. However, it was found that black olives, such as common canned variety, containing iron(II) gluconate contained little hydroxytyrosol, as iron salts are catalysts for its oxidation. Hydroxytyrosol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hydroxytyrosol is found, on average, in the highest concentration within olives and grape wines. Hydroxytyrosol has also been detected, but not quantified in, several different foods, such as cloves, fruits, olive oils, and rapes. This could make hydroxytyrosol a potential biomarker for the consumption of these foods. Hydroxytyrosol is mentioned by the scientific committee of the European Food Safety Authority as one of several olive oil polyphenols under preliminary research for the potential to affect blood lipid levels, although there is no evidence from high-quality clinical research to indicate that this effect exists. The olives, leaves and olive pulp contain large amounts of hydroxytyrosol (compared to olive oil), most of which can be recovered to produce hydroxytyrosol extracts. As of 2015, the NOAEL for hydroxytyrosol in rats is 250 mg/kg/day, with a LOAEL of 500 mg/kg/day. Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. Hydroxytyrosol is found in Cinnamomum subavenium, Clematis terniflora, Fraxinus americana, Jasminum grandiflorum, Ligustrum japonicum, Ligustrum vulgare, Peperomia duclouxii C. DC., Peperomia heyneana, Sargentodoxa cuneata, Sparganium stoloniferum, Syringa reticulata, Syringa amurensis, Syringa vulgaris and Vitis vinifera. Hydroxytyrosol was first documented in 2004 (PMID: 15476671). Hydroxytyrosol itself in pure form is a colorless, odorless liquid (PMID: 15749387) (PMID: 22948011) (PMID: 22014120) (PMID: 22924436) (PMID: 23017390) (PMID: 23244583).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047361 (Hydroxytyrosol)


  Mrv1652309261710592D          

 11 11  0  0  0  0            999 V2000
   15.9429  -28.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9409  -29.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6600  -28.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6543  -29.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3714  -28.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2296  -28.0843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3714  -29.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274  -29.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7962  -28.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0829  -28.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5110  -28.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for NP0047361 (Hydroxytyrosol)

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3D SDF for NP0047361 (Hydroxytyrosol)

  Mrv1652309261710592D          

 11 11  0  0  0  0            999 V2000
   15.9429  -28.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9409  -29.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6600  -28.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6543  -29.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3714  -28.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2296  -28.0843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3714  -29.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274  -29.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7962  -28.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0829  -28.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5110  -28.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2

> <INCHI_KEY>
JUUBCHWRXWPFFH-UHFFFAOYSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.1632

> <EXACT_MASS>
154.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.737149641805702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-hydroxyethyl)benzene-1,2-diol

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.8874266103333335

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.885859929231167

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.448236457043842

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4099441681107265

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
41.5907

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxytyrosol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047361 (Hydroxytyrosol)
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PDB for NP0047361 (Hydroxytyrosol)
HEADER    PROTEIN                                 26-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-SEP-17         0                                  
HETATM    1  C   UNK     0      29.760 -53.198   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.756 -54.731   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.099 -52.427   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.088 -55.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.427 -53.194   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      28.429 -52.424   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      32.427 -54.735   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      28.424 -55.498   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      35.086 -53.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.755 -52.422   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      36.420 -52.425   0.000  0.00  0.00           O+0
CONECT    1    2    3    6                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7   10                                                  
CONECT    6    1                                                            
CONECT    7    5    4                                                       
CONECT    8    2                                                            
CONECT    9   10   11                                                       
CONECT   10    9    5                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0047361 (Hydroxytyrosol)
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SMILES for NP0047361 (Hydroxytyrosol)
OCCC1=CC=C(O)C(O)=C1
Download
INCHI for NP0047361 (Hydroxytyrosol)
InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
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View in JSmol
Synonyms
ValueSource
3,4-DihydroxyphenylethanolChEBI
DopetChEBI
2-(3,4-Dihydroxyphenyl)ethanolHMDB
3-HydroxytyrosolHMDB
4-(2-Hydroxyethyl)-1,2-benzenediolHMDB
beta-3,4-Dihydroxyphenylethyl alcoholHMDB
2-(3'-hydroxyphenyl)ethanol
2-(3-hydroxyphenyl)ethanol
Chemical FormulaC8H10O3
Average Mass154.1632 Da
Monoisotopic Mass154.06299 Da
IUPAC Name4-(2-hydroxyethyl)benzene-1,2-diol
Traditional Namehydroxytyrosol
CAS Registry Number10597-60-1
SMILES
OCCC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
InChI KeyJUUBCHWRXWPFFH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)yupingfu424@163.comNot AvailableNot Available2023-07-17View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica napus var. napusFooDB
Cinnamomum subaveniumLOTUS Database
Clematis ternifloraLOTUS Database
Fraxinus americanaPlant
Jasminum grandiflorumLOTUS Database
Ligustrum japonicumLOTUS Database
Ligustrum vulgareLOTUS Database
Olea europaeaFooDB
Peperomia duclouxii C. DC.Plant
Peperomia heyneanaLOTUS Database
Sargentodoxa cuneataLOTUS Database
Sparganium stoloniferumLOTUS Database
Syringa reticulataLOTUS Database
Syringa reticulata subsp. amurensisPlant
Syringa vulgarisLOTUS Database
Syzygium aromaticumFooDB
Vitis viniferaLOTUS Database
Chemical Taxonomy
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassTyrosols and derivatives  
Direct ParentTyrosols  
Alternative Parents
Substituents
  • Tyrosol
    • 

  • Catechol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.13ALOGPS
logP0.89ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.59 m³·mol⁻¹ChemAxon
Polarizability15.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005784  
DrugBank IDDB12771  
Phenol Explorer Compound ID1051  
FoodDB IDFDB008754  
KNApSAcK IDC00032635  
Chemspider ID74680  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxytyrosol  
METLIN IDNot Available
PubChem Compound82755  
PDB IDNot Available
ChEBI ID68889  
Good Scents IDNot Available
References
General References
  1. O'Dowd Y, Driss F, Dang PM, Elbim C, Gougerot-Pocidalo MA, Pasquier C, El-Benna J: Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils. Biochem Pharmacol. 2004 Nov 15;68(10):2003-8. doi: 10.1016/j.bcp.2004.06.023. [PubMed:15476671  ] 
  2. D'Angelo S, Ingrosso D, Migliardi V, Sorrentino A, Donnarumma G, Baroni A, Masella L, Tufano MA, Zappia M, Galletti P: Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells. Free Radic Biol Med. 2005 Apr 1;38(7):908-19. doi: 10.1016/j.freeradbiomed.2004.12.015. [PubMed:15749387  ] 
  3. Satoh Y, Tajima K, Munekata M, Keasling JD, Lee TS: Engineering of L-tyrosine oxidation in Escherichia coli and microbial production of hydroxytyrosol. Metab Eng. 2012 Nov;14(6):603-10. doi: 10.1016/j.ymben.2012.08.002. Epub 2012 Aug 29. [PubMed:22948011  ] 
  4. Procopio A, Celia C, Nardi M, Oliverio M, Paolino D, Sindona G: Lipophilic hydroxytyrosol esters: fatty acid conjugates for potential topical administration. J Nat Prod. 2011 Nov 28;74(11):2377-81. doi: 10.1021/np200405s. Epub 2011 Oct 20. [PubMed:22014120  ] 
  5. Romero C, Brenes M: Analysis of total contents of hydroxytyrosol and tyrosol in olive oils. J Agric Food Chem. 2012 Sep 12;60(36):9017-22. doi: 10.1021/jf3026666. Epub 2012  Aug 31. [PubMed:22924436  ] 
  6. Dagdelen A, Tumen G, Ozcan MM, Dundar E: Phenolics profiles of olive fruits (Olea europaea L.) and oils from Ayvalik, Domat and Gemlik varieties at different ripening stages. Food Chem. 2013 Jan 1;136(1):41-5. doi: 10.1016/j.foodchem.2012.07.046. Epub 2012 Jul 28. [PubMed:23017390  ] 
  7. Bernini R, Merendino N, Romani A, Velotti F: Naturally occurring hydroxytyrosol: synthesis and anticancer potential. Curr Med Chem. 2013;20(5):655-70. doi: 10.2174/092986713804999367. [PubMed:23244583  ] 
  8. DOI: 10.1002/cbdv.202300161