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68592-15-4

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68592-15-4 Usage

General Description

4'-Methoxy-3',5-di-2-propenyl-(1,1'-biphenyl)-2-ol is a chemical compound that falls in the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing two benzene rings linked together by a C-C bond. Not much information is available about 4'-Methoxy-3',5-di-2-propenyl-(1,1'-biphenyl)-2-ol’s properties, uses, or potential health effects. However, as with any chemical, proper handling and usage instructions would need to be followed to ensure safety. As indicated by its name, this compound contains a biphenyl group, a methoxy group, and a hydroxyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 68592-15-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,5,9 and 2 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 68592-15:
(7*6)+(6*8)+(5*5)+(4*9)+(3*2)+(2*1)+(1*5)=164
164 % 10 = 4
So 68592-15-4 is a valid CAS Registry Number.

68592-15-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-methoxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol

1.2 Other means of identification

Product number -
Other names 3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl

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:68592-15-4 SDS

68592-15-4Synthetic route

potassium 3-allyl-4-methoxyphenyltrifluoroborate

potassium 3-allyl-4-methoxyphenyltrifluoroborate

4-allyl-2-bromo-phenol
17269-79-3

4-allyl-2-bromo-phenol

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; ruphos In 1,2-dimethoxyethane; water at 130℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;72%
With palladium diacetate; potassium carbonate; ruphos In 1,2-dimethoxyethane; water at 130℃; Reagent/catalyst; Solvent; Temperature; Suzuki-Miyaura Coupling; Sealed tube; Microwave irradiation;72%
4-allyl-2-bromo-phenol
17269-79-3

4-allyl-2-bromo-phenol

4-methoxy-3-allyl-1-phenylboronic acid
1378871-34-1

4-methoxy-3-allyl-1-phenylboronic acid

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water Suzuki coupling; Reflux; Inert atmosphere;52%
2-allyl-4-bromo-1-methoxybenzene
114303-65-0

2-allyl-4-bromo-1-methoxybenzene

1-allyl-4-oxocyclohexa-2,5-dienylethanoate
108886-90-4

1-allyl-4-oxocyclohexa-2,5-dienylethanoate

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Stage #1: 2-allyl-4-bromo-1-methoxybenzene With magnesium; ethylene dibromide In diethyl ether for 1h; Reflux;
Stage #2: 1-allyl-4-oxocyclohexa-2,5-dienylethanoate In diethyl ether at 0℃; for 0.5h;
50%
Honokiol
35354-74-6

Honokiol

methyl iodide
74-88-4

methyl iodide

A

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol
68592-19-8

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol

B

methylhonokiol
68592-15-4

methylhonokiol

C

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃;A 50%
B 20%
C 15%
With sodium hydroxide In water; dimethyl sulfoxide at 60℃;A 46%
B 20%
C 30%
With caesium carbonate In water; dimethyl sulfoxide at 60℃; Reagent/catalyst;A 21%
B 35%
C 15%
Honokiol
35354-74-6

Honokiol

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

A

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol
68592-19-8

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol

B

methylhonokiol
68592-15-4

methylhonokiol

C

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Conditions
ConditionsYield
In methanolA 13%
B 13%
C 47%
Honokiol
35354-74-6

Honokiol

methyl iodide
74-88-4

methyl iodide

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;41%
2-[(2R,4aR,8R,8aR)-8-(5,3'-Diallyl-4'-methoxy-biphenyl-2-yloxy)-4a,8-dimethyl-decahydro-naphthalen-2-yl]-propan-2-ol
143051-79-0

2-[(2R,4aR,8R,8aR)-8-(5,3'-Diallyl-4'-methoxy-biphenyl-2-yloxy)-4a,8-dimethyl-decahydro-naphthalen-2-yl]-propan-2-ol

A

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 10h; Ambient temperature;A 6 mg
B 2 mg
eudeshonokiol B
133056-10-7

eudeshonokiol B

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether / 36 h / Ambient temperature
2: 6 mg / CF3COOH / benzene / 10 h / Ambient temperature
View Scheme
Estragole
140-67-0

Estragole

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: boron trichloride-dimethyl sulfide / trans-1,2-dichloroethylene; dichloromethane / 18 h / Reflux
2.1: acetic acid / 8 h
3.1: magnesium; ethylene dibromide / diethyl ether / 1 h / Reflux
3.2: 0.5 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: methyl magnesium iodide / 180 °C
2: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; isopropylmagnesium chloride / diethyl ether / 24 h / -78 - 20 °C
3: palladium diacetate; potassium carbonate; ruphos / 1,2-dimethoxyethane; water / 0.17 h / 130 °C / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1.1: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / diethyl ether / 1.05 h / -78 °C / Inert atmosphere
2.2: 21 h / -78 - 20 °C
3.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
4-(prop-2-enyl)phenol
501-92-8

4-(prop-2-enyl)phenol

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid / 8 h
2.1: magnesium; ethylene dibromide / diethyl ether / 1 h / Reflux
2.2: 0.5 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; isopropylmagnesium chloride / diethyl ether / 24 h / -78 - 20 °C
2: palladium diacetate; potassium carbonate; ruphos / 1,2-dimethoxyethane; water / 0.17 h / 130 °C / Microwave irradiation
View Scheme
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / diethyl ether / 1.05 h / -78 °C / Inert atmosphere
1.2: 21 h / -78 - 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / diethyl ether / 0.67 h / -78 °C / Inert atmosphere
1.2: 2.5 h / 20 °C / Inert atmosphere
2.1: potassium carbonate; palladium diacetate; ruphos / 1,2-dimethoxyethane; water / 130 °C / Sealed tube; Microwave irradiation
View Scheme
5-bromo-2-methoxy-benzyl alcohol
80866-82-6

5-bromo-2-methoxy-benzyl alcohol

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Oxalyl bromide; Triphenylphosphine oxide / chloroform / 7 h
2.1: [2,2]bipyridinyl; copper(l) iodide / benzene / 5 - 20 °C
3.1: magnesium; ethylene dibromide / diethyl ether / 1 h / Reflux
3.2: 0.5 h / 0 °C
View Scheme
4-bromo-2-(bromomethyl)-1-methoxybenzene
184970-28-3

4-bromo-2-(bromomethyl)-1-methoxybenzene

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: [2,2]bipyridinyl; copper(l) iodide / benzene / 5 - 20 °C
2.1: magnesium; ethylene dibromide / diethyl ether / 1 h / Reflux
2.2: 0.5 h / 0 °C
View Scheme
2-allyl-4-bromophenol
13997-74-5

2-allyl-4-bromophenol

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 0.5 h
1.2: 4 h / 20 °C
2.1: n-butyllithium; Triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
2.2: 0.5 h / 20 °C
3.1: palladium diacetate; potassium carbonate; ruphos / 1,2-dimethoxyethane; water / 0.17 h / 130 °C / Microwave irradiation
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 0.25 h / Inert atmosphere
1.2: 1.5 h / Reflux
2.1: n-butyllithium / tetrahydrofuran / 0.83 h / -78 °C / Inert atmosphere
2.2: 2 h / -78 - 20 °C
3.1: hydrogenchloride; water / tetrahydrofuran
4.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 0.5 h
1.2: 4 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / Inert atmosphere
2.2: 0.5 h / Inert atmosphere
3.1: potassium carbonate; palladium diacetate; ruphos / 1,2-dimethoxyethane; water / 130 °C / Sealed tube; Microwave irradiation
View Scheme
2-allyl-4-bromo-1-methoxybenzene
114303-65-0

2-allyl-4-bromo-1-methoxybenzene

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium; Triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C
1.2: 0.5 h / 20 °C
2.1: palladium diacetate; potassium carbonate; ruphos / 1,2-dimethoxyethane; water / 0.17 h / 130 °C / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 0.83 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 - 20 °C
2.1: hydrogenchloride; water / tetrahydrofuran
3.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
C16H25BO3

C16H25BO3

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; water / tetrahydrofuran
2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
4-(allyloxy)bromobenzene
25244-30-8

4-(allyloxy)bromobenzene

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Reflux
2.1: potassium carbonate / acetone / 0.25 h / Inert atmosphere
2.2: 1.5 h / Reflux
3.1: n-butyllithium / tetrahydrofuran / 0.83 h / -78 °C / Inert atmosphere
3.2: 2 h / -78 - 20 °C
4.1: hydrogenchloride; water / tetrahydrofuran
5.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / Reflux; Inert atmosphere
View Scheme
Honokiol
35354-74-6

Honokiol

dimethyl sulfate
77-78-1

dimethyl sulfate

A

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol
68592-19-8

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol

B

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
With potassium hydroxide Microwave irradiation;
4-bromo-phenol
106-41-2

4-bromo-phenol

methylhonokiol
68592-15-4

methylhonokiol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 5 h / Reflux
2.1: potassium carbonate / acetone / 0.5 h
2.2: 4 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / Inert atmosphere
3.2: 0.5 h / Inert atmosphere
4.1: potassium carbonate; palladium diacetate; ruphos / 1,2-dimethoxyethane; water / 130 °C / Sealed tube; Microwave irradiation
View Scheme
methylhonokiol
68592-15-4

methylhonokiol

4'-methoxy-3',5-di-n-propyl-[1,1'-biphenyl]-2-ol
82793-36-0

4'-methoxy-3',5-di-n-propyl-[1,1'-biphenyl]-2-ol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;99%
With palladium 10% on activated carbon; hydrogen In methanol for 1h;98%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; for 21h;97%
With palladium on activated charcoal; hydrogen97%
methylhonokiol
68592-15-4

methylhonokiol

4'-O-methyl-3-nitro-honokiol
1315334-03-2

4'-O-methyl-3-nitro-honokiol

Conditions
ConditionsYield
With nitric acid In hexane; water at 20℃;99%
With nitric acid In ethyl acetate
methylhonokiol
68592-15-4

methylhonokiol

methyl iodide
74-88-4

methyl iodide

Dimethylhonokiol
68592-18-7

Dimethylhonokiol

Conditions
ConditionsYield
Stage #1: methylhonokiol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 3h;
98%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

methylhonokiol
68592-15-4

methylhonokiol

4'-methoxy-3',5-bis(3-methylbut-2-en-1-yl)-[1,1'-biphenyl]-2-ol
1375102-90-1

4'-methoxy-3',5-bis(3-methylbut-2-en-1-yl)-[1,1'-biphenyl]-2-ol

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 24h; Inert atmosphere;95%
acetic anhydride
108-24-7

acetic anhydride

methylhonokiol
68592-15-4

methylhonokiol

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl acetate
68592-20-1

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl acetate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h; Inert atmosphere;93%
With pyridine87%
methylhonokiol
68592-15-4

methylhonokiol

methyl chloroacetate
96-34-4

methyl chloroacetate

C22H24O4

C22H24O4

Conditions
ConditionsYield
With caesium carbonate; triethylamine; potassium iodide In acetone at 20℃; for 24h;89%
methylhonokiol
68592-15-4

methylhonokiol

4'-methoxy-3',5-bis(oxiran-2-ylmethyl)-[1,1'-biphenyl]-2-ol
1375102-87-6

4'-methoxy-3',5-bis(oxiran-2-ylmethyl)-[1,1'-biphenyl]-2-ol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In benzene87%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78 - 20℃; for 24h; Inert atmosphere;53%
methylhonokiol
68592-15-4

methylhonokiol

prenyl bromide
870-63-3

prenyl bromide

3',5-diallyl-4'-methoxy-2-((3-methylbut-2-en-1-yl)oxy)-1,1'-biphenyl
1375102-74-1

3',5-diallyl-4'-methoxy-2-((3-methylbut-2-en-1-yl)oxy)-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: methylhonokiol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: prenyl bromide In N,N-dimethyl-formamide at 20℃; for 5h;
86%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

methylhonokiol
68592-15-4

methylhonokiol

benzylamine
100-46-9

benzylamine

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl benzylcarbamate
1375102-79-6

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl benzylcarbamate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; methylhonokiol With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: benzylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;
81%
morpholine
110-91-8

morpholine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

methylhonokiol
68592-15-4

methylhonokiol

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl morpholine-4-carboxylate
1389251-25-5

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl morpholine-4-carboxylate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; methylhonokiol With pyridine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: morpholine In dichloromethane at 20℃; for 12h;
68%
methylhonokiol
68592-15-4

methylhonokiol

3'-bromo-3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl
1375102-84-3

3'-bromo-3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: methylhonokiol With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere;
66%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

methylhonokiol
68592-15-4

methylhonokiol

1-amino-2-propene
107-11-9

1-amino-2-propene

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl allylcarbamate
1375102-77-4

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl allylcarbamate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; methylhonokiol With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: 1-amino-2-propene In dichloromethane at 20℃; for 12h; Inert atmosphere;
65%
methylhonokiol
68592-15-4

methylhonokiol

isopropyl bromide
75-26-3

isopropyl bromide

3',5-diallyl-2-isopropoxy-4'-methoxy-1,1'-biphenyl
1375102-72-9

3',5-diallyl-2-isopropoxy-4'-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: methylhonokiol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: isopropyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;
60%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

methylhonokiol
68592-15-4

methylhonokiol

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl benzyl(methyl)carbamate
1375102-80-9

3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-yl benzyl(methyl)carbamate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; methylhonokiol With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: benzyl-methyl-amine In dichloromethane at 20℃; for 12h; Inert atmosphere;
59%
13-(5-iodopentyl)-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium iodide

13-(5-iodopentyl)-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium iodide

methylhonokiol
68592-15-4

methylhonokiol

13-(5-((3′,5-diallyl-4′-methoxy-[1,1′-biphenyl]-2-yl)oxy)pentyl)-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]-isoquinolin-7-ium iodide

13-(5-((3′,5-diallyl-4′-methoxy-[1,1′-biphenyl]-2-yl)oxy)pentyl)-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]-isoquinolin-7-ium iodide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;48%
With potassium carbonate In acetone at 50℃;
methylhonokiol
68592-15-4

methylhonokiol

3',5-di-(2,3-dihydroxypropyl)-4'-methoxy-biphenyl-2-ol
1315333-89-1

3',5-di-(2,3-dihydroxypropyl)-4'-methoxy-biphenyl-2-ol

Conditions
ConditionsYield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 2h; Inert atmosphere; Reflux;40%
methylhonokiol
68592-15-4

methylhonokiol

5-allyl-3'-(3-hydroxypropyl)-4'-methoxy-[1,1'-biphenyl]-2-ol
1375102-89-8

5-allyl-3'-(3-hydroxypropyl)-4'-methoxy-[1,1'-biphenyl]-2-ol

Conditions
ConditionsYield
Stage #1: methylhonokiol With borane-THF In tetrahydrofuran at 0 - 20℃; for 2.08333h; Inert atmosphere;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at -10 - 70℃; for 2h; Inert atmosphere;
36%
methylhonokiol
68592-15-4

methylhonokiol

3',5-diallyl-3-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol
1375102-82-1

3',5-diallyl-3-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol

Conditions
ConditionsYield
Stage #1: methylhonokiol With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at -78 - 20℃; for 0.666667h; Inert atmosphere;
Stage #2: With 1,3-dichloro-5,5-dimethylhydantoin In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere;
32%
methylhonokiol
68592-15-4

methylhonokiol

A

4'-methoxy-3'-((Z)-1-propenyl)-5-(2-propenyl)biphenyl-2-ol
1178919-03-3

4'-methoxy-3'-((Z)-1-propenyl)-5-(2-propenyl)biphenyl-2-ol

B

4'-methoxy-3'-((E)-1-propenyl)-5-(2-propenyl)biphenyl-2-ol
1178919-00-0

4'-methoxy-3'-((E)-1-propenyl)-5-(2-propenyl)biphenyl-2-ol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 21h; Inert atmosphere; Reflux;
With potassium tert-butylate In tetrahydrofuran

68592-15-4Relevant articles and documents

Synthesis and in vitro antitumor evaluation of honokiol derivatives

Zhu, Meilin,Li, Bohan,Ma, Hui,Huang, Xuenan,Wang, Haotian,Dai, Yiqun,Li, Yu,Li, Hong-Mei,Wu, Cheng-Zhu

, (2020)

Honokiol is a natural bioactive neolignan and has been widely researched and structural modified as an anticancer agent. In this paper, 18 honokiol derivatives were synthesized and investigated for their antitumor activity. Among these, the promising compound 5a exhibited much higher anti-proliferative activity with IC50 value of 10.41 μM. Transwell assays showed that 5a could significantly inhibit the invasion and migration of I-10 cells at 2.5 μM, which was further confirmed by the western blotting experiments with down-regulation of the HIF-1α and its associated downstream proteins MMP-2 and MMP-9. Overall, these results provided useful suggestion for further structural optimization of honokiol derivatives.

Anticancer Effects of Honokiol via Mitochondrial Dysfunction Are Strongly Enhanced by the Mitochondria-Targeting Carrier Berberine

Shi, Xiaojia,Zhang, Tao,Lou, Hongxiang,Song, Huina,Li, Changhao,Fan, Peihong

, p. 11786 - 11800 (2020)

Mitochondrion is a favorable therapeutic target in cancer, given its regulation of bioenergetics and cell death. Honokiol exhibits antiproliferative effects through mitochondria-mediated death signaling. To enhance its anticancer potential and selectivity, we conjugated honokiol to berberine, a mitochondria-targeting carrier. All designed derivatives displayed 1 order of magnitude increased cytotoxicity compared with the parent compounds, especially with massive cytoplasmic vacuoles. Biological evaluation demonstrated the representative compound 6b localized within the mitochondria, and mitochondrial dilation resulted in vacuolization. 6b induced vacuolation-associated cell death and apoptosis with obvious mitochondrial dysfunction, as demonstrated by booming reactive oxygen species generation, opening mitochondrial permeability transition pore, and reducing mitochondrial membrane potential. The targeting property also conferred 6b with selectivity for tumor cells compared to normal cells. 6b inhibited cancer cell proliferation in the zebrafish xenograft model. These results demonstrate that berberine-linked honokiol derivatives open up a direction for novel mitochondrial-targeting antitumor agents.

Method for Synthesizing 4-O-Methylhonokiol

-

, (2016/12/22)

The present invention refers to a the active compounds useful 4-O-methylhonokiol-chemical method synthesis of relates to a preparation. Of the existing method according to the present invention extracted from natural 4-O the method obtaining-methylhonokiol produce highly pure crude high yield by a unidirectional photocoupler the product may be-methylhonokiol 4-O unit is off.

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