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Tyrosol

Tyrosol structure

CAS No:
501-94-0
Formula:
C8H10O2
Chemical Name:
Tyrosol
Synonyms:
Benzeneethanol,4-hydroxy-;Tyrosol;Phenethyl alcohol,p-hydroxy-;4-Hydroxybenzeneethanol;p-Hydroxyphenethyl alcohol;β-(p-Hydroxyphenyl)ethanol;p-Tyrosol;β-(4-Hydroxyphenyl)ethanol;2-(4-Hydroxyphenyl)ethanol;2-(p-Hydroxyphenyl)ethanol;4-(2-Hydroxyethyl)phenol;4-Hydroxyphenethyl alcohol;p-(2-Hydroxyethyl)phenol;4-Hydroxyphenylethanol;2-(4-Hydroxyphenyl)ethyl alcohol;Tyrosol C;NSC 59876;p-HPEA
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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].

Solid

2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent and a fungal metabolite. It derives from a 2-phenylethanol.

Tyrosol Basic Attributes

Molecular Weight：

138.16400

Exact Mass：

138.16

EC Number：

207-930-8

UNII：

1AK4MU3SNX

NSC Number：

59876

DSSTox ID：

DTXSID8060111

HScode：

2907299090

Characteristics

PSA：

40.46000

XLogP3：

0.4

Appearance：

Solid

Density：

1.168 g/cm3

Melting Point：

90 °C

Boiling Point：

310 °C

Flash Point：

143.2ºC

Refractive Index：

1.577

Water Solubility：

H2O: slightly soluble

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Collision Cross Section：

138.71 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|138.2 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S24/25

Marks：

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

Drug Information

MeSH：

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

MeSH Entry Terms：

4-hydroxyphenylethanol

Tyrosol Use and Manufacturing

Methods of Manufacturing

The formation of 4-(2-hydroxyethyl)phenol. This compoundwas prepared following a literature procedure.54 To a solution of 2-(4-hydroxyphenyl)acetic acid (760 mg, 5 mmol) in ethanol (20 mL) wasadded sulfuric acid (27 μL, 0.5 mmol), and the resulting mixture washeated at reflux for 3 h. After completion monitored by TLC, the solventwas removed under reduced pressure, and the crude product was dissolvedin anhydrous THF (20 mL), followed by the addition of LiAlH4(228 mg, 6 mmol) slowly at 0 °C, and the resulting mixture was allowedto warm to RT for 12 h. After completion monitored by TLC, the solutionwas cooled to 0 °C, and quenched by Na2SO4·10H2O solid and filteredthrough Celite®. The solvent was removed under reduced pressureand the residue was diluted with H2O (20 mL) and extracted with ethylacetate (3×20 mL). The combined organic layers were dried overMgSO4 and concentrated in vacuo. The crude product was purified byflash chromatography (hexane/ethyl acetate 5:1→2:1) to give theproduct as an off-white solid (600 mg, 87percent). Rf (hexane/ethyl acetate2:1): 0.30; 1H NMR (400 MHz, CDCl3): δ 7.10 (2H, dd, J=2.0, 6.4 Hz), 6.78 (2H, dd, J=2.0, 6.4 Hz), 4.83 (1H, br.s), 3.83 (2H, dd, J=6.4, 15.0 Hz), 2.80 (2H, t, J=6.4 Hz); 13C NMR (100 MHz, CDCl3): δ 154.4, 130.6, 130.3, 115.6, 64.0, 38.4. The spectroscopic data matched thatreported in the literature.54A solution of methyl 2-(4-hydroxyphenyl)acetate (3.0 g, 18.07 mmol), in THF (20 mL) was added to a stirred suspension of LAH (0.89 g, 23.49 mmol) in THF (20 mL) at 0° C. The stirring was continued at RT for 4 h. Excess of LAH was quenched with saturated Na2SO4 solution and the precipitate formed was filtered off. The filtrated was extracted with ethyl acetate and the organic extract was washed with brine, dried (Na2SO4) and evaporated to dryness. Column purification with 50percent ethyl acetate-pet ether yielded the title compound (1.1 g, 44percent) as a white solid. [0240] Mp: 88-92° C. [0241] 1H NMR (200 MHz, CDCl3+DMSO-d6): δ 2.75 (t, J=7.1 Hz, 2H); 3.75 (t, J=6.3 Hz, 2H); 6.75 (d, J=8.3 Hz, 2H); 7.03 (d, J=8.3 Hz, 2H). [0242] Mass m/z (CI): 138 [M].

Uses

Phenolic antioxidant.

Manufacturing Info：

Benzeneethanol, 4-hydroxy-: ACTIVE

Use Classification：

Food additives -> Flavoring Agents

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:138.16
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:138.068079557
Monoisotopic Mass:138.068079557
Topological Polar Surface Area:40.5
Heavy Atom Count:10
Complexity:85.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Methanol

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