4-Hydroxyphenyl ethanol

Names

[ CAS No. ]:
501-94-0

[ Name ]:
4-Hydroxyphenyl ethanol

[Synonym ]:
4-(2-Hydroxyethyl)phenol
2-(4-Hydroxyphenyl)ethyl Alcohol
4-Hydroxyphenylethanol
β-(4-Hydroxyphenyl)ethanol
4-[(2S)-2-Amino-3-hydroxypropyl]phenol
(S)-4-(2-Amino-3-hydroxypropyl)phenol
b-(4-Hydroxyphenyl)ethanol
Benzenepropanol, β-amino-4-hydroxy-, (βS)-
tyrosinol
4-(2-Hydroxyethyl)benzolol
phenethyl alcohol, 4-hydroxy-
p-Hydroxyphenethyl alcohol
Benzenepropanol, β-amino-4-hydroxy-, (S)-
UNII-1AK4μ3SNX
2-(4-Hydroxyphenyl)ethanol
Ethanol, 2-(4-hydroxyphenyl)-
2-(4-Hydroxyphenyl)ethan-1-ol
(S)-b-Amino-4-hydroxybenzenepropanol
4-hydroxybenzeneethanol
MFCD00002902
β-(p-Hydroxyphenyl)ethanol
4-Hydroxyphenethyl alcohol
EINECS 207-930-8
Benzeneethanol, 4-hydroxy-
p-Hydroxyphenylethanol
4-Hydroxyphenethyl alcohol,Tyrosol,p-HPEA
4-Hydroxyphenylethyl alcohol
b-(p-Hydroxyphenyl)ethanol
4-Hydroxyphenyl ethanol
Tyrosol

Biological Activity

[Description]:

Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

[Related Catalog]:

Signaling Pathways >> NF-κB >> NF-κB

Natural Products >> Phenols

Research Areas >> Inflammation/Immunology

[In Vitro]

Tyrosol (1.6 mM) significantly increases the cell viability of cultured astrocytes exposed to oxygen glucose deprivation (OGD)[1]. Tyrosol (1.6 mM) attenuates the released TNF-α and IL-6 level from astrocyte via regulating Janus N-terminal kinase (JNK) [1]. The reduction of cytokines from astrocyte might be due to its inhibition of astrocyte activation and regulation of STAT3 signaling pathway since Tyrosol (1.6 mM) attenuates the expression level of GFAP (glial fibrillary acidic protein) and the phosphorylation of STAT3[1]. Tyrosol prevents the degradation of IκBα and the increase of IκBα phosphorylation in astrocytes exposed to OGD, which leads to the suppression of NF-κB function during ischemia[1].

[In Vivo]

Sub-plantar injection of carrageenan causes a noticeable increase in paw thickness, reaching a peak after 2 h post-injection. This effect is reduced when Tyrosol (0.5 mg/kg) or Tyrosol-sulphate is injected prior to the treatment with carrageenan. Similar AUC values for paw oedema are obtained after the administration of Tyrosol at a dose of 0.5 mg/kg and Tyrosol-sulphate at a dose of 0.1 mg/kg.

[References]

[1]. Luo G, et al. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation in in vitro oxygen glucose deprivation. Neurochem Int. 2018 Dec;121:140-145.

[2]. Muriana FJG, et al. Tyrosol and its metabolites as antioxidative and anti-inflammatory molecules in human endothelial cells. Food Funct. 2017 Aug 1;8(8):2905-2914.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
375.2±27.0 °C at 760 mmHg

[ Melting Point ]:
89-92 °C(lit.)

[ Molecular Formula ]:
C₈H₁₀O₂

[ Molecular Weight ]:
138.16

[ Flash Point ]:
180.7±23.7 °C

[ PSA ]:
40.46000

[ LogP ]:
0.04

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.598

[ Water Solubility ]:
slightly soluble

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2907299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2907299090

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

Articles

Effect of different aging techniques on the polysaccharide and phenolic composition and sensory characteristics of Syrah red wines fermented using different yeast strains.

Food Chem. 179 , 116-26, (2015)

The effect of high levels of the polysaccharide Saccharomyces cerevisiae yeast strain (HPS) and another conventional yeast strain (FERM) on the polysaccharide and phenolic composition of Syrah red win...

Effect of selected Saccharomyces cerevisiae yeast strains and different aging techniques on the polysaccharide and polyphenolic composition and sensorial characteristics of Cabernet Sauvignon red wines.

J. Sci. Food Agric. 95 , 2132-44, (2015)

The objective of this work was to study the effect of two Saccharomyces cerevisiae yeast strains with different capabilities of polysaccharide liberation during alcoholic fermentation in addition to s...

Multicommuted flow injection method for fast photometric determination of phenolic compounds in commercial virgin olive oil samples.

Talanta 147 , 531-6, (2015)

A multicommuted flow injection method has been developed for the determination of phenolic species in virgin olive oil samples. The method is based on the inhibitory effect of antioxidants on a stable...