p-hydroxyphenethyl alcohol
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
3,4-dihydroxyphenylacetate
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
2-<3,4-bis(benzyloxy)phenyl>ethanol
hydroxytyrosol
Conditions | Yield |
---|---|
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; |
2-(3,4-dihydroxyphenyl)acetic acid methyl ester
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
2-(3,4-dihydroxyphenyl)ethyl acetate
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
2-(3,4-dimethoxyphenyl)ethyl alcohol
hydroxytyrosol
Conditions | Yield |
---|---|
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; |
hydroxytyrosol
Conditions | Yield |
---|---|
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% |
1-chloro-2-(3,4-dihydroxyphenyl)ethane
hydroxytyrosol
Conditions | Yield |
---|---|
With water for 4h; Microwave irradiation; | 94.8% |
homovanillyl alcohol
hydroxytyrosol
Conditions | Yield |
---|---|
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 |
2-hydroxy-3′,4′-dihydroxyacetophenone
hydroxytyrosol
Conditions | Yield |
---|---|
With water; hydrogen; palladium 10% on activated carbon In ethyl acetate at 40℃; under 3750.38 Torr; for 16h; Product distribution / selectivity; | 87.8% |
With water; hydrogen; palladium 10% on activated carbon In tert-butyl methyl ether at 40℃; under 3750.38 Torr; for 7.5 - 25h; Product distribution / selectivity; | 87% |
With hydrogen; 5% activated charcoal-supported ruthenium catalyst In tert-butyl methyl ether at 40℃; under 3750.38 Torr; Product distribution / selectivity; | 82.1% |
3,4-dihydroxyphenethyl trifluoroacetate
hydroxytyrosol
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 24h; Product distribution / selectivity; | 87% |
Stage #1: 3,4-dihydroxyphenethyl trifluoroacetate With potassium hydroxide; water In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity; | 80% |
3-bromo-4-hydroxyphenylethyl alcohol
hydroxytyrosol
Conditions | Yield |
---|---|
With water; copper 8-hydroxyquinolinate; potassium hydroxide at 100℃; for 6h; Reagent/catalyst; Temperature; | 86.52% |
Multi-step reaction with 4 steps 1.1: copper(I) bromide; sodium methylate / methanol / 15 h / 100 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 12 h / 50 °C 3.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: copper(I) bromide; sodium methylate / methanol / 15 h / 100 °C 2: acetic acid / 12 h / 50 °C 3: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 4: hydrogenchloride / dichloromethane / 24 h / 20 °C View Scheme |
hydroxytyrosol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 0 - 70℃; under 750.075 Torr; for 2.5h; Temperature; | 85.2% |
2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate
hydroxytyrosol
Conditions | Yield |
---|---|
Stage #1: 2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate With potassium hydroxide; water In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity; | 85% |
With potassium hydroxide; water In tetrahydrofuran at 20℃; for 0.5h; | 85% |
oleuropeine
hydroxytyrosol
Conditions | Yield |
---|---|
With sodium hydroxide for 2h; | 11% |
With sulfuric acid at 37℃; for 3h; | |
Multi-step reaction with 2 steps 1.1: camphorsulfonic acid; 4 Angstroem molecular sieves / CHCl3 / 6 h / Heating 1.2: 13 mg / aq. NaOH / 2 h / Heating 2.1: 97 percent / Amberlyst 15 / methanol / 3 h / Heating View Scheme |
methanol
2′-acetylacteoside
A
hydroxytyrosol
B
Methyl caffeate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Heating; |
methanol
2'-acetylisoacteoside
A
hydroxytyrosol
B
Methyl caffeate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Product distribution; Heating; |
methanol
2-(3,4-dihydroxyphenyl)-ethyl O-α-L-rhamnopyranosyl-(1->3)-O-[β-D-clucopyranosyl-(1->6)]-2-O-acetyl-4-O-[(E)-caffeoyl]-β-D-glucopyranoside
A
hydroxytyrosol
B
Methyl caffeate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Product distribution; Heating; |
methanol
tubuloside D
A
hydroxytyrosol
B
methyl 4-hydroxycinnamate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Product distribution; Heating; |
methanol
tubuloside C
A
hydroxytyrosol
B
Methyl caffeate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Product distribution; Heating; |
Conditions | Yield |
---|---|
pivaloyl chloride at 80℃; for 3h; |
multifloroside
hydroxytyrosol
Conditions | Yield |
---|---|
With sodium hydroxide for 3.5h; Ambient temperature; Yield given; |
cis-verbascoside
A
D-Glucose
B
L-rhamnose
C
caffeic acid
D
hydroxytyrosol
Conditions | Yield |
---|---|
With hydrogenchloride; potassium hydroxide 1.) MeOH, H2O, reflux, 3 h; 2.) MeOH, H2O, reflux; |
(3,4-Diacetoxy-phenyl)-acetic acid methyl ester
hydroxytyrosol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
forsythiaside
A
D-Glucose
B
L-rhamnose
C
caffeic acid
D
hydroxytyrosol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide Ambient temperature; hydrolysis; |
Conditions | Yield |
---|---|
With hesperidinase In water at 32℃; for 48h; Product distribution; |
Conditions | Yield |
---|---|
In methanol for 0.5h; Heating; Title compound not separated from byproducts; |
echinacoside
acetyl chloride
A
hydroxytyrosol
B
Methyl caffeate
Conditions | Yield |
---|---|
In methanol for 0.5h; Heating; Title compound not separated from byproducts; |
3,4-dihydroxyphenylacetate
A
hydroxytyrosol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; diazomethyl-trimethyl-silane 1.) methanol, ether, hexane, RT, 0.5 h, 2.) methanol, ether, hexane, water, 0 deg C, 1.5 h; Yield given; Multistep reaction. Yields of byproduct given; |
hydroxytyrosol
acetic anhydride
2-(3,4-diacetoxyphenyl)-ethyl acetate
Conditions | Yield |
---|---|
In neat (no solvent) Molecular sieve; Microwave irradiation; Green chemistry; | 100% |
With erbium(III) triflate at 20℃; for 2h; Inert atmosphere; | 80% |
With pyridine; dmap In tetrahydrofuran at 20℃; for 7h; | 75% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
vinyl octanoate
hydroxytyrosol
octanoic acid-3,4-dihydroxyphenylethyl ester
Conditions | Yield |
---|---|
With Candida antarctica lipase In tert-butyl methyl ether at 40℃; for 1h; Enzymatic reaction; | 99% |
With Novozym 435 at 40℃; for 1h; Enzymatic reaction; | |
With Candida antarctica lipase In tert-butyl methyl ether at 60℃; Enzymatic reaction; |
hydroxytyrosol
Conditions | Yield |
---|---|
With Amberlyst 15; water-d2 at 90℃; for 24h; | 98% |
With Amberlyst 15; water-d2 at 90℃; for 24h; Substitution; | |
With nafion resin; water-d2 at 90℃; for 24h; |
hydroxytyrosol
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction; | 98% |
With toluene-4-sulfonic acid In methanol at 4℃; for 24h; | 80% |
for 0.166667h; oxa-Pictet-Spengler cyclisation; |
hydroxytyrosol
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction; | 98% |
With toluene-4-sulfonic acid In methanol at 4℃; for 24h; | 80% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 2h; Pictet-Spengler Synthesis; Reflux; | 98% |
With toluene-4-sulfonic acid In methanol for 2h; Pictet-Spengler Synthesis; Reflux; | 98% |
With toluene-4-sulfonic acid In methanol for 2h; Pictet-Spengler Synthesis; Reflux; | 98% |
hexadecanoic acid ethyl ester
hydroxytyrosol
Conditions | Yield |
---|---|
With Novozym 435 at 37℃; | 98% |
hydroxytyrosol
carbonic acid dimethyl ester
2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 1h; | 98% |
With sulfuric acid |
Conditions | Yield |
---|---|
With pyridine In toluene at 20℃; Cooling with ice; | 98% |
In toluene for 0.75h; Cooling with ice; | 72% |
hydroxytyrosol
Conditions | Yield |
---|---|
With Amberlyst 15; tritium oxide at 90℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With Candida antarctica lipase In various solvent(s) at 40℃; for 0.583333h; | 96.5% |
With Novozym 435 at 40℃; for 1h; Enzymatic reaction; | |
With Candida antarctica lipase In tert-butyl methyl ether at 60℃; Enzymatic reaction; |
vinyl propionate
hydroxytyrosol
Conditions | Yield |
---|---|
With Candida antarctica lipase In various solvent(s) at 40℃; for 0.583333h; | 95.1% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 4℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction; | 95% |
With toluene-4-sulfonic acid In methanol at 4℃; for 24h; | 60% |
With sulfuric acid at 20℃; for 2.5h; | 55% |
for 0.166667h; oxa-Pictet-Spengler cyclisation; |
Conditions | Yield |
---|---|
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction; | 95% |
for 0.166667h; oxa-Pictet-Spengler cyclisation; |
Conditions | Yield |
---|---|
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction; | 95% |
Conditions | Yield |
---|---|
With Candida antarctica lipase In various solvent(s) at 40℃; for 0.583333h; | 95% |
With Novozym 435 at 40℃; for 1h; Enzymatic reaction; |
hydroxytyrosol
carbonic acid dimethyl ester
3,4-dihydroxyphenethyl methyl ether
Conditions | Yield |
---|---|
With Amberlyst 15 for 12h; Reflux; | 95% |
Conditions | Yield |
---|---|
With Novozym 435 at 37℃; | 94% |
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%.
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%.
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
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View