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10597-60-1

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  • Natural Material Manufacturer Directly Offer ISO9001, HALAL, Kosher, USDA BioPreferred Program and COSMOS Certificated 20%, 99% Hydroxytyrosol 3,4-Dihydrozyphenylethanol by Bio-fermentation

    Cas No: 10597-60-1

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10597-60-1 Usage

Description

3,4-Dihydroxyphenylethanol, also known as Hydroxytyrosol, is a phenolic compound found in olive oil. It is a member of the catechols and a primary alcohol, derived from 2-(4-hydroxyphenyl)ethanol. This substance is a primary reference substance with assigned absolute purity, considering chromatographic purity, water, residual solvents, and inorganic impurities. It exhibits antioxidant and antineoplastic activities and has a role as a metabolite, an antioxidant, and an antineoplastic agent.

Uses

Used in Cardiovascular Applications:
3,4-Dihydroxyphenylethanol is used as a cardiovascular drug for the prevention and treatment of arteriosclerosis, hypertension, heart disease, and cerebral hemorrhage. It has been found to be superior to similar drugs in these applications.
Used in Cancer Treatment:
3,4-Dihydroxyphenylethanol is used as an antineoplastic agent, inhibiting the proliferation rate of cancer cells and inducing apoptosis.
Used in Beauty and Health Care Products:
3,4-Dihydroxyphenylethanol is used as an ingredient in beauty and health care products, where it effectively enhances skin elasticity and moisturizing, and has anti-wrinkle and anti-aging effects.
Used in Antioxidant Applications:
3,4-Dihydroxyphenylethanol is used as an antioxidant, protecting LDL from both biological and chemical oxidation, suggesting a potential mechanism for the protective effects of olive oil against atherosclerosis.
Used in Enzyme Inhibition:
3,4-Dihydroxyphenylethanol is used as an inhibitor of 12and 5-LO enzymes, with IC50 values of 4.2 and 13 μM for rat platelet 12-LO and rat neutrophil 5-LO, respectively. It does not inhibit COX activity and may actually enhance it.
Used in Pharmaceutical Research:
3,4-Dihydroxyphenylethanol is used as a primary reference substance in pharmaceutical research, with its exact purity value found on the certificate provided by PhytoLab GmbH & Co. KG.
Used in the Production of Hydroxytyrosol:
3,4-Dihydroxyphenylethanol is used in the production of Hydroxytyrosol, a tyrosol metabolite and a strong antioxidant found in olive oil.

Characteristics

Hydroxytyrosol displays much more effective antioxidant characteristics, such as the scavenging of free radicals, breaking peroxidative chain reactions, preventing lipid peroxidation, inhibiting hypochlorous acid derived radicals, and so on, compared with other phenolic compounds in olive oil. It could be used in the dermocosmetic industry for the creation of products for protecting the skin from oxidative stress or used as a preservative in the food technology.

Biochem/physiol Actions

Metabolite of oleuropein. Antioxidant. Inhibits the rate of cancer cell proliferation and induces cancer cell apoptosis.

Source

Hydroxytyrosol is also known as 2-(3,4-dihydroxyphenyl)-ethanol (3,4-DHPEA) and as DOPET. Hydroxytyrosol is mainly found in olive oil as secoiridoid derivatives, as acetate and in free form. Both hydroxytyrosol and its derivatives arise from oleuropein (hydroxytyro- sol esterified with elenolic acid), present in olives during the extraction of olive oil.Wine has proven to be another important source of hydroxytyrosol in the Mediterranean diet, and is formed in wine from tyrosol during alcoholic fermentation. Hydroxytyrosol was firstly found in Italian wines by Di Tommaso et al., and later in other Italian and Greek wines. Some authors describe a higher concentration in red wines (3.66-4.20 mg/L-1) than in white wines (1.72-1.92mg/L-1). Finally, Minuti et al. obtained hydroxytyrosol concen- trations between 1.8 and 3.1 mg L-1 in red wine. Thus, scientific literature shows that wine is an important source of hydroxytyrosol in the diet, along with olive oil.

Check Digit Verification of cas no

The CAS Registry Mumber 10597-60-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,9 and 7 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 10597-60:
(7*1)+(6*0)+(5*5)+(4*9)+(3*7)+(2*6)+(1*0)=101
101 % 10 = 1
So 10597-60-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2

10597-60-1 Well-known Company Product Price

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  • (91404)  3-Hydroxytyrosol  analytical standard

  • 10597-60-1

  • 91404-5MG

  • 916.11CNY

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10597-60-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name hydroxytyrosol

1.2 Other means of identification

Product number -
Other names 3,4-Dihydroxyphenethyl Alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10597-60-1 SDS

10597-60-1Synthetic route

p-hydroxyphenethyl alcohol
501-94-0

p-hydroxyphenethyl alcohol

hydroxytyrosol
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%
3,4-dihydroxyphenylacetate
102-32-9

3,4-dihydroxyphenylacetate

hydroxytyrosol
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%
2-<3,4-bis(benzyloxy)phenyl>ethanol
96826-11-8

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

hydroxytyrosol
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;
2-(3,4-dihydroxyphenyl)acetic acid methyl ester
25379-88-8

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

hydroxytyrosol
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%
2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-ol
119054-91-0

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

hydroxytyrosol
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%
2-(3,4-dihydroxyphenyl)ethyl acetate
69039-02-7

2-(3,4-dihydroxyphenyl)ethyl acetate

hydroxytyrosol
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%
2-(3,4-dimethoxyphenyl)ethyl alcohol
7417-21-2

2-(3,4-dimethoxyphenyl)ethyl alcohol

hydroxytyrosol
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

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

hydroxytyrosol
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%
1-chloro-2-(3,4-dihydroxyphenyl)ethane
104693-00-7

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

hydroxytyrosol
10597-60-1

hydroxytyrosol

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

homovanillyl alcohol

hydroxytyrosol
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
2-hydroxy-3′,4′-dihydroxyacetophenone
29477-54-1

2-hydroxy-3′,4′-dihydroxyacetophenone

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
1056355-55-5

3,4-dihydroxyphenethyl trifluoroacetate

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
196081-78-4

3-bromo-4-hydroxyphenylethyl alcohol

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
3-amino-4-hydroxy-phenylethyl acetate

3-amino-4-hydroxy-phenylethyl acetate

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
953422-34-9

2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
32619-42-4

oleuropeine

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
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
67-56-1

methanol

2′-acetylacteoside
94492-24-7

2′-acetylacteoside

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Heating;
methanol
67-56-1

methanol

2'-acetylisoacteoside
112516-04-8

2'-acetylisoacteoside

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Product distribution; Heating;
methanol
67-56-1

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
112516-05-9

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
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Product distribution; Heating;
methanol
67-56-1

methanol

tubuloside D
112503-94-3

tubuloside D

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Product distribution; Heating;
methanol
67-56-1

methanol

tubuloside C
112503-95-4

tubuloside C

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Product distribution; Heating;
methanol
67-56-1

methanol

jionoside E

jionoside E

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

Conditions
ConditionsYield
pivaloyl chloride at 80℃; for 3h;
multifloroside
131836-10-7

multifloroside

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With sodium hydroxide for 3.5h; Ambient temperature; Yield given;
cis-verbascoside
97747-56-3

cis-verbascoside

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
73-34-7

L-rhamnose

C

caffeic acid
331-39-5

caffeic acid

D

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide 1.) MeOH, H2O, reflux, 3 h; 2.) MeOH, H2O, reflux;
(3,4-Diacetoxy-phenyl)-acetic acid methyl ester
35400-16-9

(3,4-Diacetoxy-phenyl)-acetic acid methyl ester

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
forsythiaside
79916-77-1

forsythiaside

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
73-34-7

L-rhamnose

C

caffeic acid
331-39-5

caffeic acid

D

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide Ambient temperature; hydrolysis;
rossicaside A
112664-03-6

rossicaside A

A

caffeic acid
331-39-5

caffeic acid

B

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hesperidinase In water at 32℃; for 48h; Product distribution;
acetyl chloride
75-36-5

acetyl chloride

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;
echinacoside
737806-07-4

echinacoside

acetyl chloride
75-36-5

acetyl chloride

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
In methanol for 0.5h; Heating; Title compound not separated from byproducts;
3,4-dihydroxyphenylacetate
102-32-9

3,4-dihydroxyphenylacetate

A

hydroxytyrosol
10597-60-1

hydroxytyrosol

B

3,4-dihydroxyphenylic acid ester of 2-(3,4-dihydroxyphenyl)ethanol

3,4-dihydroxyphenylic acid ester of 2-(3,4-dihydroxyphenyl)ethanol

Conditions
ConditionsYield
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
10597-60-1

hydroxytyrosol

acetic anhydride
108-24-7

acetic anhydride

2-(3,4-diacetoxyphenyl)-ethyl acetate
86214-97-3

2-(3,4-diacetoxyphenyl)-ethyl acetate

Conditions
ConditionsYield
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%
hydroxytyrosol
10597-60-1

hydroxytyrosol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C26H52O3Si3

C26H52O3Si3

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;100%
vinyl octanoate
818-44-0

vinyl octanoate

hydroxytyrosol
10597-60-1

hydroxytyrosol

octanoic acid-3,4-dihydroxyphenylethyl ester
205241-38-9

octanoic acid-3,4-dihydroxyphenylethyl ester

Conditions
ConditionsYield
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
10597-60-1

hydroxytyrosol

C8H7(2)H3O3

C8H7(2)H3O3

Conditions
ConditionsYield
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
10597-60-1

hydroxytyrosol

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(p-methoxyphenyl)-6,7-dihydroxyisochroman

1-(p-methoxyphenyl)-6,7-dihydroxyisochroman

Conditions
ConditionsYield
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
10597-60-1

hydroxytyrosol

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

1-(m-hydroxyphenyl)-6,7-dihydroxyisochroman

1-(m-hydroxyphenyl)-6,7-dihydroxyisochroman

Conditions
ConditionsYield
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%
hydroxytyrosol
10597-60-1

hydroxytyrosol

acetone
67-64-1

acetone

6,7-dihydroxy-1,1-dimethylisochromane

6,7-dihydroxy-1,1-dimethylisochromane

Conditions
ConditionsYield
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
628-97-7

hexadecanoic acid ethyl ester

hydroxytyrosol
10597-60-1

hydroxytyrosol

palmitic acid-3,4-dihydroxyphenylethyl ester

palmitic acid-3,4-dihydroxyphenylethyl ester

Conditions
ConditionsYield
With Novozym 435 at 37℃;98%
hydroxytyrosol
10597-60-1

hydroxytyrosol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate
953422-34-9

2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 1h;98%
With sulfuric acid
hydroxytyrosol
10597-60-1

hydroxytyrosol

Hexanoyl chloride
142-61-0

Hexanoyl chloride

3-hydroxytyrosol trihexanoate

3-hydroxytyrosol trihexanoate

Conditions
ConditionsYield
With pyridine In toluene at 20℃; Cooling with ice;98%
In toluene for 0.75h; Cooling with ice;72%
hydroxytyrosol
10597-60-1

hydroxytyrosol

C8H7(3)H3O3

C8H7(3)H3O3

Conditions
ConditionsYield
With Amberlyst 15; tritium oxide at 90℃; for 24h;97%
vinyl n-butyrate
123-20-6

vinyl n-butyrate

hydroxytyrosol
10597-60-1

hydroxytyrosol

butyric acid-3,4-dihydroxyphenylethyl ester

butyric acid-3,4-dihydroxyphenylethyl ester

Conditions
ConditionsYield
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
105-38-4

vinyl propionate

hydroxytyrosol
10597-60-1

hydroxytyrosol

propionic acid 2-(3,4-dihydroxyphenyl)ethyl ester

propionic acid 2-(3,4-dihydroxyphenyl)ethyl ester

Conditions
ConditionsYield
With Candida antarctica lipase In various solvent(s) at 40℃; for 0.583333h;95.1%
hydroxytyrosol
10597-60-1

hydroxytyrosol

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

1-(3-nitro-phenyl)-isochroman-6,7-diol

1-(3-nitro-phenyl)-isochroman-6,7-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 4℃; for 24h;95%
hydroxytyrosol
10597-60-1

hydroxytyrosol

benzaldehyde
100-52-7

benzaldehyde

1-phenyl-6,7-dihydroxyisochroman

1-phenyl-6,7-dihydroxyisochroman

Conditions
ConditionsYield
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;
nonan-1-al
124-19-6

nonan-1-al

hydroxytyrosol
10597-60-1

hydroxytyrosol

1-(1'-octyl)-6,7-dihydroxyisochroman

1-(1'-octyl)-6,7-dihydroxyisochroman

Conditions
ConditionsYield
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;
hydroxytyrosol
10597-60-1

hydroxytyrosol

propionaldehyde
123-38-6

propionaldehyde

1-ethyl-6,7-dihydroxyisochroman

1-ethyl-6,7-dihydroxyisochroman

Conditions
ConditionsYield
With molecular sieve; toluene-4-sulfonic acid In methanol at 4℃; for 24h; oxa-Pictet Spengler reaction;95%
vinyl acetate
108-05-4

vinyl acetate

hydroxytyrosol
10597-60-1

hydroxytyrosol

2-(3,4-dihydroxyphenyl)ethyl acetate
69039-02-7

2-(3,4-dihydroxyphenyl)ethyl acetate

Conditions
ConditionsYield
With Candida antarctica lipase In various solvent(s) at 40℃; for 0.583333h;95%
With Novozym 435 at 40℃; for 1h; Enzymatic reaction;
hydroxytyrosol
10597-60-1

hydroxytyrosol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3,4-dihydroxyphenethyl methyl ether
1156543-91-7

3,4-dihydroxyphenethyl methyl ether

Conditions
ConditionsYield
With Amberlyst 15 for 12h; Reflux;95%
stearic acid ethyl ester
111-61-5

stearic acid ethyl ester

hydroxytyrosol
10597-60-1

hydroxytyrosol

2-(3,4-dihydroxyphenyl)-ethyl stearate

2-(3,4-dihydroxyphenyl)-ethyl stearate

Conditions
ConditionsYield
With Novozym 435 at 37℃;94%

10597-60-1Relevant articles and documents

Olea europaea chemicals repellent to Dacus oleae females

Scalzo,Scarpati,Verzegnassi,Vita

, p. 1813 - 1823 (1994)

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Antioxidant activity of olive phenols: Mechanistic investigation and characterization of oxidation products by mass spectrometry

Roche, Marjolaine,Dufour, Claire,Mora, Nathalie,Dangles, Olivier

, p. 423 - 430 (2005)

In this work, the antioxidant activity of olive phenols is first characterized by their stoichiometries ntot (number of radicals trapped per antioxidant molecule) and their rate constants for the first H-atom abstraction k1, by the stable radical DPPH. It appears that oleuropein, hydroxytyrosol and caffeic acid have the largest k1 values, whereas dihydrocaffeic acid, an intestinal metabolite of caffeic acid, is the best antioxidant in terms of ntot. For phenols with a catechol moiety ntot1 is higher than two, implying an antioxidant effect of their primarily formed oxidation products. A HPLC-MS analysis of the main products formed in the AAPH-induced oxidation of olive phenols reveals the presence of dimers and trimers. With hydroxytyrosol and dihydrocaffeic acid, oligomerization can take place with the addition of water molecules. The antioxidant activity of olive phenols is then evaluated by their ability to inhibit the AAPH-induced peroxidation of linoleic acid in SDS micelles. It is shown that olive phenols and quercetin act as retardants rather than chain breakers like α-tocopherol. From a detailed mechanistic investigation, it appears that the inhibition of lipid peroxidation by olive phenols can be satisfactorily interpreted by assuming that they essentially reduce the AAPH-derived initiating radicals. Overall, olive phenols prove to be efficient scavengers of hydrophilic peroxyl radicals with a long lasting antioxidant effect owing to the residual activity of some of their oxidation products.

Synthesis of tritium-labeled hydroxytyrosol, a phenolic compound found in olive oil

Tuck, Kellie L.,Tan, Hai-Wei,Hayball, Peter J.

, p. 4087 - 4090 (2000)

(3,4-Dihydroxyphenyl)ethanol, commonly known as hydroxytyrosol (1), is the major phenolic antioxidant compound in olive oil, and it contributes to the beneficial properties of olive oil. Bioavailability and metabolism studies of this compound are extremely limited, in part, related to unavailability of radiolabeled compound. Studies with radiolabeled compounds enable use of sensitive radiometric analytical methods as well as aiding elucidation of metabolic and elimination pathways. In the present study a route for the formation of hydroxytyrosol (1), by reduction of the corresponding acid 2 with tetrabutylammonium boronate, was found. Methods for the incorporation of a tritium label in 1 were investigated and successfully accomplished. Tritiated hydroxytyrosol (1t) was synthesized with a specific activity of 66 Ci/mol. The stability of unlabeled and labeled hydroxytyrosol was also investigated.

A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters

Capasso, Renato,Evidente, Antonio,Avolio, Salvatore,Solla, Francesco

, p. 1745 - 1748 (1999)

Hydroxytyrosol, a polyphenol with very interesting antioxidant properties, which naturally occurs in virgin olive oil and mainly in olive oil mill waste waters, was synthesized by reducing 3,4-dihydroxyphenylacetic acid with LiAlH4 in tetrahydrofuran under refluxing for 2 h. The yield of reaction was 82.8%. The spectroscopic and HPLC data of the synthesized compound proved to coincide fully with those of a pure sample obtained by the chromatographic recovery from olive oil mill waste waters (yield = 91 mg/L). This synthetic method appears to be the most convenient compared with those reported in the literature and is more convenient than the chromatographic recovery. The tri- and diacetyl derivatives of the synthetic compound were also prepared for structure-bioactivity relationship studies. A brief discussion is given on the economical and ecological aspects regarding the production of hydroxytyrosol.

Determination of hydroxytyrosol in plasma by HPLC

Ruiz-Gutierrez,Juan,Cert,Planas

, p. 4458 - 4461 (2000)

Hydroxytyrosol (2-(3,4-dihydroxyphenyl)ethanol), a phenolic compound present in extravirgin olive oil, has been reported to contribute to the prevention of cardiovascular disease. The present study describes an accurate and reproducible reversed-phase HPLC method to measure hydroxytyrosol in plasma. This compound was extracted from acidified plasma by solid-phase extraction using an Oasis HLB copolymer. The plasma sample was rinsed with water and methanol in water (5:95; v/v). Hydroxytyrosol was eluted with methanol, which was subsequently evaporated under a nitrogen stream. Analysis by HPLC with diode array-UV detection was carried out using a C18 column and a gradient elution with acidified water and methanol/acetonitrile (50:50; v/v). The method was validated by the analyses of plasma samples spiked with pure hydroxytyrosol, obtaining a linear correlation (0.9986) and precision with a coefficient of variation ranging from 0.79 to 6.66%. The recovery was ?100%, and the limit of detection was 37 ng/mL. The oral administration of hydroxytyrosol to rats and its subsequent detection in plasma showed that the method is suitable for pharmacokinetic studies.

High-yielding preparation of a stable precursor of hydroxytyrosol by total synthesis and from the natural glycoside oleuropein

Gambacorta, Augusto,Tofani, Daniela,Bernini, Roberta,Migliorini, Antonella

, p. 3386 - 3391 (2007)

The unprecedented acetonide of the antioxidant hydroxytyrosol has been synthesized by a two-step high-yielding procedure and found to be both purifiable by chromatography and stable over a wide pH range. The protection stabilizes hydroxytyrosol against oxidation, thereby allowing long-term storage. The protection can quantitatively be removed, under nonaqueous conditions, to afford pure hydroxytyrosol suitable for use as an additive in food and cosmetic preparations. Extension of the same methodology to the natural and easily accessible glycoside oleuropein, followed by saponification of the resulting complex mixture of acetonides, allowed hydroxytyrosol acetonide to be recovered in high yield. This constitutes a new interesting methodology to obtain the antioxidant hydroxytyrosol.

HYDROXYCINNAMIC ACID ESTERS OF PHENETHYLALCOHOL GLYCOSIDES FROM REHMANNIA GLUTINOSA VAR. PURPUREA

Sasaki, Hiroshi,Nishimura, Hiroaki,Chin (Chen Zhengxiong), Masao,Mitsuhashi, Hiroshi

, p. 875 - 880 (1989)

Five new hydroxycinnamic acid esters of phenethylalcohol glycosides named jionosides C, D, E, A2 and B2, together with nine known compounds, have been isolated from roots of Rehmannia glutinosa var. purpurea and their structures elucidated on the basis of chemical and spectral evidences. Key Word Index-Rehmannia glutinosa var. purpurea; Scrophulariaceae; phenethylalcohol glycosides; jionosides.

Determination of Synthetic Hydroxytyrosol in Rat Plasma by GC-MS

Bai, Chen,Yan, Xiaojun,Takenaka, Makiko,Sekiya, Keizo,Nagata, Tadahiro

, p. 3998 - 4001 (1998)

2-(3,4-Dihydroxyphenyl)ethanol (DPE), the major phenolic compound in olive oil, may contribute the antioxidative activities and other beneficial effects to olive oil. However, the lack of commercial available DPE and procedures sensitive enough to quantitatively determine DPE in body fluids have limited the bioavailability and metabolism studies on this phenolic compound. In the present study, DPE was synthesized with high yield and high purity and administered orally to rats. DPE concentration in rat plasma, after absorption, was measured using a sensitive GC-MS-SIM method. The results indicated that the highest level of DPE in plasma was detected at 5-10 min after administration. During this period, the concentration of DPE fluctuated widely with the individual.

Production of hydroxytyrosol from hydroxylation of tyrosol by Rhodococcus pyridinivorans 3HYL DSM109178

Anissi, Jaouad,Sendide, Khalid,Ouardaoui, Abdelkrim,Benlemlih, Mohammed,El Hassouni, Mohammed

, p. 418 - 428 (2021)

Hydroxytyrosol (4-(2-hydroxyethyl)-1,2-benzenediol) is the most known bioactive compound from the plant Olea europaea (olive tree). To date, few biocatalysis processes allowing efficient production of hydroxytyrosol from potential substrates including, tyrosol (2-(4-hydroxy) phenyl ethanol) and tyrosine have been reported. In this paper, we report for a Gram-positive bacterium that produces hydroxytyrosol via conversion of tyrosol and/or L-tyrosine, identified as a Rhodococcus pyridinivorans based on phenotypic characteristics and 16S rDNA sequence, and designated R. pyridinivorans strain 3HYL DSM109178. Interestingly, strain 3HYL shows an outstanding production of hydroxytyrosol from tyrosol up to 16.4 ± 0.23 mmol/L with high kinetic parameters exceeding the reported values. However, a slight downstream metabolism of the product is assigned to the wild-type strain during the stationary phase of growth. The plasmid-cured strain was obtained using random chemical mutagenesis, designated R. pyridinivorans 3HYL-AO, and was able to produce hydroxytyrosol, with yields up to 21.75 ± 0.34 mmol/L. Moreover, the plasmid-cured strain exhibited a significant reduction in the transformation to its acetic acid forms compared to the wild-type strain as depicted by HPLC analysis. Comparison of kinetic data of the bioconversion/accumulation process between the wild type and mutant strain, in the presence and absence of L-tyrosine, and thus suggesting the occurrence of an upstream pathway for synthesis of tyrosol via (L)-tyrosine.

Whole-cell carboxylate reduction for the synthesis of 3-hydroxytyrosol

Napora-Wijata, Kamila,Robins, Karen,Osorio-Lozada, Antonio,Winkler, Margit

, p. 1089 - 1095 (2014)

3-Hydroxytyrosol (3-HT) is a phenolic antioxidant that has a number of beneficial effects on human health and is a valuable building block in the synthesis of various pharmaceuticals. Herein, we report a new method for the production of 3-HT through reduction of 3,4-dihydroxyphenylacetic acid. The reduction was performed in whole Escherichia coli BL21 (DE3) cells overexpressing carboxylic acid reductase from Nocardia and phosphopantetheinyl transferase from E. coli. An endogenous E. coli aldehyde reducing activity turned out to be highly efficient for further reduction of the aldehyde intermediate to the desired alcohol. The influence of different buffer components, cofactors, and cofactor recycling systems was investigated. A very economic combination of glucose, citrate, and air proved sufficient for recycling of the essential cofactors ATP and NAD(P)H. Selected crucial parameters were then further optimized within a "design of experiments" approach. Finally, first preparative-scale bioreductions resulted in pure 3-HT. All in a cell's work: An enzymatic carboxylic acid reduction is the key step of a new route to the potent antioxidant from olives: 3-hydroxytyrosol. In addition to the substrate 3,4-dihydroxyphenylacetic acid, only citrate, glucose, and oxygen are required to regenerate the essential cofactors ATP and NAD(P)H. CAR=carboxylate reductase; PPTase= phosphopantetheinyl transferase.

Acteoside as the analgesic principle of Cedron (Lippia triphylla), a Peruvian medicinal plant

Nakamura, Tomonori,Okuyama, Emi,Tsukada, Atsushi,Yamazaki, Mikio,Satake, Motoyoshi,Nishibe, Sansei,Deyama, Takeshi,Moriya, Akira,Maruno, Masao,Nishimura, Hiroaki

, p. 499 - 504 (1997)

Acteoside (verbascoside) was isolated as an analgesic principle from Cedron (leaves and stem of Lippia triphylla (L'HER) O. KUNTZE; Verbenaceae), a Peruvian medicinal plant, by activity-guided separation. The compound exhibited analgesia on acetic acid-induced writhing and on tail pressure pain in mice by the oral administration of 300mg/kg and 100mg/kg, respectively. Acteoside also caused weak sedation by its effect on the prolongation of pentobarbital-induced anesthesia and on the depression of locomotion enhanced by methamphetamine. An intravenous injection of acteoside reduced the effective dose to 2mg/kg by the writhing method. Thirteen related compounds were tested for the activity by intravenous and oral administration to obtain information on the active structure.

Oxidative chemistry of the natural antioxidant hydroxytyrosol: Hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways

De Lucia, Maria,Panzella, Lucia,Pezzella, Alessandro,Napolitano, Alessandra,D'Ischia, Marco

, p. 1273 - 1278 (2006)

Oxidation of the natural antioxidant hydroxytyrosol (1) with peroxidase/H2O2 in phosphate buffer at pH 7.4 led to the formation of two main ethyl acetate-extractable products. These could be isolated by preparative TLC after reduction and acetylation, and were identified as the tetraacetyl derivative of 2-(2,4,5-trihydroxyphenyl)ethanol (3) and the heptaacetyl derivative of the pentahydroxybiphenyl 4 by 2D NMR and MS analysis. Similar oxidation of 4-methylcatechol gave, after the same work-up, the acetylated derivatives of 1,2,4-trihydroxy-5-methylbenzene (5) and the pentahydroxybiphenyl 6. Mechanistic experiments suggested that hydrogen peroxide affects the course of the oxidation of 1 by adding to the first formed o-quinone to give a hydroxyquinone intermediate. This could bring nucleophilic attack to the o-quinone of 1 to give the dimer 4. These results disclose novel oxidative pathways of 4-alkylcatechols and provide an improved chemical basis to enquire into the mechanism of the antioxidant action of 1.

Novel approach to the detection and quantification of phenolic compounds in olive oil based on 31P nuclear magnetic resonance spectroscopy

Christophoridou, Stella,Dais, Photis

, p. 656 - 664 (2006)

31P NMR spectroscopy has been employed to detect and quantify phenolic compounds in the polar fraction of virgin olive oil. This novel analytical method is based on the derivatization of the hydroxyl and carboxyl groups of phenolic compounds with 2-chloro-4,4,5,5-tetramethyldioxaphospholane and the identification of the phosphitylated compounds on the basis of the 31P chemical shifts. Quantification of a large number of phenolic compounds in virgin olive oil can be accomplished by integration of the appropriate signals in the 31P NMR spectrum and the use of the phosphitylated cyclohexanol as internal standard. Finally, the validity of this technique for quantitative measurements was thoroughly examined.

A two-step process for the synthesis of hydroxytyrosol

Ziosi, Paolo,Paolucci, Claudio,Santarelli, Francesco,Tabanelli, Tommaso,Passeri, Sauro,Cavani, Fabrizio,Righi, Paolo

, p. 2202 - 2210 (2018)

A new process for the synthesis of hydroxytyrosol (3,4-dihy-droxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two-step approach is reported. Catechol is first reacted with 2,2-dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative with > 90 % conversion of the limiting reactant and about 70 % selectivity to the desired para-hydroxyalkylat-ed compound. Thereafter, the intermediate is hydrogenated to hydroxytyrosol by using a Pd/C catalyst, with total conversion of the mandelic derivative and 68 % selectivity. This two-step process is the first example of a synthetic pathway for hydroxytyrosol that does not involve the use of halogenated components or reduction methodologies that produce stoichiometric waste. It also avoids the complex procedure currently used for hydroxytyrosol purification when it is extracted from wastewa-ter of olive oil production.

Regioselectivity of Cobalamin-Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate

Pompei, Simona,Grimm, Christopher,Farnberger, Judith E.,Schober, Lukas,Kroutil, Wolfgang

, p. 5977 - 5983 (2020)

Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4-substituted catechols was investigated employing the cobalamin-dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta- or para-position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta-selective with 4-substituted catechols bearing hydrophilic groups, it was para-selective for hydrophobic substituents. Furthermore, the presence of water miscible co-solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.

Isolation of natural compounds from Phlomis stewartii showing α-glucosidase inhibitory activity

Jabeen, Bushra,Riaz, Naheed,Saleem, Muhammad,Naveed, Muhammad Akram,Ashraf, Muhammad,Alam, Umber,Rafiq, Hafiza Mehwish,Tareen, Rasool Bakhsh,Jabbar, Abdul

, p. 443 - 448 (2013)

Stewartiiside (1), a phenylethanoid glycoside and three 28-nortriterpenoids: stewertiisins A-C [(17R)-19(18 → 17)-abeo-3α, 18β,23,24-tetrahydroxy-28-norolean-12-ene, 2; (17R)-19(18 → 17)-abeo-2α,16β,18β,23,24-pentahydroxy-28-norolean-12-en-3-one, 3; (17R)-19(18 → 17)-abeo-2α,3α,23,24-tetrahydroxy-28- noroleane-11,13-diene, 4] together with eight known compounds: lunariifolioside (5), notohamosin A (6), phlomispentanol (7), isorhamnetin 3-(6-p-coumaroyl)- β-d-glucopyranoside (8), tiliroside (9), caffeic acid (10), p-hydrxybenzoic acid (11) and oleanolic acid (12) were isolated from the ethyl acetate soluble fraction of the methanolic extract of whole plant of Phlomis stewartii. The structures of these isolates (1-12) were elucidated by the combination of 1D (1H and 13C NMR), 2D (HMQC, HMBC COSY, NOESY) NMR spectroscopy and mass spectrometry (EIMS, HREIMS, FABMS, HRFABMS) and in comparison with literature data of related compounds. All the isolates (1-12) showed α-glucosidase inhibitory activity with IC50 values ranging between 14.5 and 355.4 μM, whereas, compounds 1, 5, 9 and 10 showed promising α-glucosidase inhibitory activity with IC50 values below 30 μM.

Hydroxytyrosol, a phenolic compound from virgin olive oil, prevents macrophage activation

Maiuri, Maria Chiara,De Stefano, Daniela,Di Meglio, Paola,Irace, Carlo,Savarese, Maria,Sacchi, Raffaele,Cinelli, Maria Pia,Carnuccio, Rosa

, p. 457 - 465 (2005)

We investigated the effect of hydroxytyrosol (HT), a phenolic compound from virgin olive oil, on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in J774 murine macrophages stimulated with lipopolysaccharide (LPS). Incubation of cells with LPS caused an increase in iNOS and COX-2 mRNA and protein level as well as ROS generation, which was prevented by HT. In addition, HT blocked the activation of nuclear factor-κB (NF-κB), signal transducer and activator of transcription-1α (STAT-1α) and interferon regulatory factor-1 (IRF-1). These results, showing that HT down-regulates iNOS and COX-2 gene expression by preventing NF-κB, STAT-1α and IRF-1 activation mediated through LPS-induced ROS generation, suggest that it may represent a non-toxic agent for the control of pro-inflammatory genes. Springer-Verlag 2005.

Production of high hydroxytyrosol yields via tyrosol conversion by Pseudomonas aeruginosa immobilized resting cells

Bouallagui, Zouhaier,Sayadi, Sami

, p. 9906 - 9911 (2006)

An immobilized whole cell system was successfully performed to produce the most powerful antioxidant, hydroxytyrosol. Bioconversion of tyrosol into hydroxytyrosol was achieved via the immobilization of Pseudomonas aeruginosa resting cells in calcium alginate beads. Immobilization was advantageous as it allows immobilized cells to tolerate a greater tyrosol concentration than free cells. The bioconversion yield reached 86% in the presence of 5 g L-1 of tyrosol when cells immobilized in alginate beads were carried out in single batches. Evaluation of kinetic parameters showed the maintenance of the same catalytic efficiency expressed as Kcat/Km for both free and immobilized cells. The use of immobilized cells in repeated batches demonstrated a notable activity stabilization since the biocatalyst reusability was extended for at least four batches with a molar yield greater than 85%.

Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis

O'Reilly, Elaine,O'Sullivan, Rachel,Ryan, James,Taday, Freya

supporting information, (2022/01/04)

Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.

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