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3,4-Dihydroxyphenylethanol
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Name

3,4-Dihydroxyphenylethanol

 EINECS 600-704-3
CAS No. 10597-60-1 Density 1.321 g/cm3
PSA 60.69000 LogP 0.63260
Solubility N/A Melting Point N/A
Formula C8H10O3 Boiling Point 355.4 °C at 760 mmHg
Molecular Weight 154.166 Flash Point 182.6 °C
Transport Information N/A Appearance Yellow green powder
Safety 26 Risk Codes  Xi:;
Molecular Structure Molecular Structure of 10597-60-1 (3,4-Dihydroxyphenylethanol) Hazard Symbols IrritantXi
Synonyms

Phenethylalcohol, 3,4-dihydroxy- (6CI,7CI,8CI);1-(2-Hydroxyethyl)-3,4-dihydroxybenzene;2-(3,4-Dihydroxyphenyl)ethanol;2-(3,4-Dihydroxyphenyl)ethyl alcohol;3,4-DHPEA;3,4-Dihydroxy-b-phenethyl alcohol;3,4-Dihydroxyphenethyl alcohol;3,4-Dihydroxyphenylethyl alcohol;3-Hydroxytyrosol;4-(2-Hydroxymethyl)-1,2-benzenediol;Ba 2774;Homoprotocatechuyl alcohol;Hydroxytyrosol;b-(3,4-Dihydroxyphenyl)ethanol;b-(3,4-Dihydroxyphenyl)ethylalcohol;3,4-Dihydroxyphenylethanol;

Article Data 100

3,4-Dihydroxyphenylethanol Synthetic route

501-94-0

p-hydroxyphenethyl alcohol

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With polymer-supported IBX In dimethyl carbonate at 20℃; for 1h; chemoselective reaction;100%
With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; pH=7.0; Enzymatic reaction;97.5%
Stage #1: p-hydroxyphenethyl alcohol at 20℃; for 1h;
Stage #2: With sodium dithionite; water for 0.5h;		90%
102-32-9

3,4-dihydroxyphenylacetate

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With (C4H9)NBH4 In tetrahydrofuran; dichloromethane at 20℃; for 2h;99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 8h;90%
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Reduction; Heating;79%
96826-11-8

2-<3,4-bis(benzyloxy)phenyl>ethanol

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran for 3h;98%
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 2h; Inert atmosphere;96%
With palladium on activated charcoal; hydrogen In ethanol under 3800.26 Torr; for 24h;
25379-88-8

2-(3,4-dihydroxyphenyl)acetic acid methyl ester

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
Stage #1: 2-(3,4-dihydroxyphenyl)acetic acid methyl ester With sodium tetrahydroborate In water at 0 - 24.5℃; for 8.16667h;
Stage #2: With hydrogenchloride; water at 0 - 5℃; for 0.25h; Product distribution / selectivity;		97%
Stage #1: 2-(3,4-dihydroxyphenyl)acetic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3.33333h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 0.333333h; Product distribution / selectivity;		96.7%
Stage #1: 2-(3,4-dihydroxyphenyl)acetic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3.33333h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 0.333333h;		96.7%
119054-91-0

2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With Amberlyst 15 In methanol for 3h; Heating;97%
Stage #1: 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol With water; acetic acid at 120℃; for 20h;
Stage #2: With water; sodium hydroxide In ethanol at 20℃; for 3h;
Stage #3: With hydrogenchloride In ethanol; water		94%
With Amberlyst 15 In methanol for 8h; Reflux;78%
69039-02-7

2-(3,4-dihydroxyphenyl)ethyl acetate

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 20℃; for 24h;96%
With hydrogenchloride In dichloromethane at 20℃; for 24h;95%
With hydrogenchloride In dichloromethane at 20℃; for 12h;94%
7417-21-2

2-(3,4-dimethoxyphenyl)ethyl alcohol

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
Stage #1: 2-(3,4-dimethoxyphenyl)ethyl alcohol With aluminum (III) chloride In ethanethiol at 0 - 20℃; for 17h;
Stage #2: With hydrogenchloride; water In ethanethiol Cooling with ice;		95%
With aluminium trichloride In benzene Heating;

1,2-dibenzyloxy-4-(2-benzyloxyvinyl)benzene

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 70℃; under 2585.81 Torr; for 12h; Solvent; Reagent/catalyst; Pressure; Green chemistry;95%
104693-00-7

1-chloro-2-(3,4-dihydroxyphenyl)ethane

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With water for 4h; Microwave irradiation;94.8%
2380-78-1

homovanillyl alcohol

10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
Stage #1: homovanillyl alcohol With aluminum (III) chloride In ethanethiol at 0 - 20℃; for 42h;
Stage #2: With hydrogenchloride; water Cooling with ice;		94.7%
With sodium periodate In water; ethyl acetate Concentration; Reagent/catalyst; Temperature; Solvent; Time;78%
Stage #1: homovanillyl alcohol In tetrahydrofuran at 20℃; Darkness;
Stage #2: With sodium dithionite; water In tetrahydrofuran Darkness; chemoselective reaction;		42%
With polymer-supported IBX In dimethyl carbonate regioselective reaction;
Multi-step reaction with 3 steps
1: acetic acid / 12 h / 50 °C
2: boron tribromide / dichloromethane / -20 °C / Inert atmosphere
3: hydrogenchloride / dichloromethane / 24 h / 20 °C
View Scheme

3,4-Dihydroxyphenylethanol Specification

The CAS registry number of 3,4-Dihydroxyphenylethanol is 10597-60-1. The IUPAC name is 4-(2-hydroxyethyl)benzene-1,2-diol. In addition, the molecular formula is C8H10O3. What's more, it is a phytochemical with antioxidant properties. In nature, it is found in olive leaf which is used for medical purposes. It also exists in olive oil. Besides, it is used in the synthesis of cardiovascular drugs.

Physical properties about 3,4-Dihydroxyphenylethanol are: (1)ACD/LogP: 0.115; (2)ACD/LogD (pH 5.5): 0.12; (3)ACD/LogD (pH 7.4): 0.11; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 27.51; (7)ACD/KOC (pH 7.4): 27.33; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.623; (12)Molar Refractivity: 41.1 cm3; (13)Molar Volume: 116.616 cm3 ; (14)Polarizability: 16.293 10-24cm3; (15)Surface Tension: 64.6119995117188 dyne/cm; (16)Density: 1.322 g/cm3; (17)Flash Point: 182.611 °C; (18)Enthalpy of Vaporization: 63.374 kJ/mol; (19)Boiling Point: 355.431 °C at 760 mmHg

Preparation of 3,4-Dihydroxyphenylethanol: it can be prepared by (3,4-dihydroxy-phenyl)-acetic acid. This reaction will need reagent (C4H9)NBH4, and solvents CH2Cl2 and tetrahydrofuran. The reaction time is 2 hours at reaction temperature of 20 °C. The yield is about 99%.

3,4-Dihydroxyphenylethanol can be prepared by (3,4-dihydroxy-phenyl)-acetic acid

Uses of 3,4-Dihydroxyphenylethanol: it is used to prevent and control lung cancer, breast cancer, ovarian cancer and prostate cancer. And it has been demonstrated to be a monoamine oxidase inhibitor (MAOI). In addition, it can react with 3-methyl-butan-2-one to get 1-isopropyl-1-methyl-isochroman-6,7-diol. This reaction will need reagent p-toluenesulfonic acid and solvent methanol. The reaction time is 48 hours at reaction temperature of 4 °C. The yield is about 35%.

3,4-Dihydroxyphenylethanol can react with 3-methyl-butan-2-one to get 1-isopropyl-1-methyl-isochroman-6,7-diol

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(cc1O)CCO
(2)InChI: InChI=1/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
(3)InChIKey: JUUBCHWRXWPFFH-UHFFFAOYAM

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