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Chemical Structure| 501-94-0 Chemical Structure| 501-94-0
Chemical Structure| 501-94-0

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2-(4-Hydroxyphenyl)ethanol is a natural product isolated and purified from the leaves of Canarium album, which significantly protects dopaminergic neurons from MPP(+)-induced degradation, and reveals potential neuroprotective mechanism of tyrosol.

Synonyms: NSC 59876; 4-Hydroxyphenylethanol; NSC 59876, p-HPEA, Tyrosol

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Product Details of Tyrosol

CAS No. :501-94-0
Formula : C8H10O2
M.W : 138.16
SMILES Code : C1=CC(=CC=C1CCO)O
Synonyms :
NSC 59876; 4-Hydroxyphenylethanol; NSC 59876, p-HPEA, Tyrosol
MDL No. :MFCD00002902
InChI Key :YCCILVSKPBXVIP-UHFFFAOYSA-N
Pubchem ID :10393

Safety of Tyrosol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Tyrosol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 501-94-0 ]
  • Downstream synthetic route of [ 501-94-0 ]

[ 501-94-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 133-99-3 ]
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  • [ 10338-51-9 ]
YieldReaction ConditionsOperation in experiment
6.7% With β-glucosidase from Aspergillus niger In water at 37℃; for 3 h; Enzymatic reaction Reaction mixture (100 mL) comprising of 2.0725 g (1.5 mmol) tyrosol, 15.4 g cellobiose and Novozyme 188 (735 U of β-glucosidase) in distilled water was incubated at 37 °C. The reaction was stopped after 3 h by boiling in water bath for 5 min, centrifuged for 10 min at 4500 rpm and filtered through 0.22 m filter (25 mm diameter). The filtrate was applied on column of Sephadex LH-20 (75 cm long, 3.2 mm i.d.) equilibrated and eluted with distilled water. Tyrosol was regenerated by gradient of ethanol. The process of purification was monitored by TLC. Fractions containing salidroside were collected and concentrated in vacuo. To remove coloured substances originating from the enzyme, the material was further subjected to flash chromatography with gradient of methanol in chloroform. Fractions containing pure salidroside were concentrated and crystallised from mixture of methanol and chloroform (1:5, v/v).
References: [1] Letters in Organic Chemistry, 2009, vol. 6, # 2, p. 115 - 119.
[2] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 113, p. 23 - 28.
  • 2
  • [ 492-61-5 ]
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  • [ 10338-51-9 ]
YieldReaction ConditionsOperation in experiment
24.3% With β-glycosidase from black plum seeds; 1-octyl-3-methylimidazolium hexafluorophosphate In 1,4-dioxane; aq. phosphate buffer at 50℃; for 72 h; Enzymatic reaction General procedure: The different seed meals were prepared as described by Yuet al. [10]. The reaction was performed in a 10 ml Erlenmeyershaking flask capped with a septum containing 1.6 ml dioxane, 0.4 ml phosphate buffer (pH 6.8, 100 mmol/L), 0.5 mmolD-glucose, 5 mmol tyrosol, and different fruit seed meal at 50°C and 200 r/min. Aliquots were withdrawn at specified timeintervals from the reaction mixture, and then diluted 50 timeswith the corresponding mobile phase prior to HPLC analysis.One unit of -glycosidase activity (U) was defined as theamount of enzyme required to produce 1 μmol salidroside inthe first hour under the above conditions. The specific activitiesof the black plum seed meal, apple seed meal, peach seed meal,bitter almond seed meal, and prune seed meal were 27.6, 23.4,25.9, 13.5, and 19.7 U/g.
References: [1] Chinese Journal of Catalysis, 2012, vol. 33, # 7-8, p. 1161 - 1165.
[2] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 74, # 1-2, p. 24 - 28.
  • 3
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  • [ 153-18-4 ]
  • [ 10338-51-9 ]
References: [1] ChemSusChem, 2017, vol. 10, # 9, p. 2040 - 2045.
  • 4
  • [ 50-99-7 ]
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References: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2095 - 2097.
  • 5
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References: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 4, p. 581 - 586.
[2] Phytochemistry, 1988, vol. 27, # 6, p. 1813 - 1816.
[3] Tetrahedron, 1989, vol. 45, # 12, p. 3673 - 3682.
[4] Synthetic Communications, 2011, vol. 41, # 17, p. 2594 - 2600.
  • 6
  • [ 501-94-0 ]
  • [ 2492-87-7 ]
  • [ 10338-51-9 ]
References: [1] Tetrahedron Asymmetry, 1999, vol. 10, # 12, p. 2429 - 2439.
  • 7
  • [ 2280-44-6 ]
  • [ 501-94-0 ]
  • [ 10338-51-9 ]
References: [1] Asian Journal of Chemistry, 2013, vol. 25, # 9, p. 5095 - 5098.
  • 8
  • [ 501-94-0 ]
  • [ 5391-18-4 ]
  • [ 10338-51-9 ]
References: [1] Biocatalysis and Biotransformation, 2018, .
 

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