528-43-8

Basic information

• Product Name: Magnolol
• Synonyms: 1’-Biphenyl)-2,2’-diol,5’,5-di-2-propenyl-(1;5,5'-DIALLYL-BIPHENYL-2,2'-DIOL;5,5'-DIALLYL-2,2'-BIPHENYLDIOL;5,5'-DIALLYL-2,2'-DIHYDROXYBIPHENYL;MAGNOLOL;Magnolia officinalis Rehd.et Wils;MAGNOLOL 98.0% BY HPLC;Honokiol std.
• CAS NO: 528-43-8
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.33
• EINECS: 200-001-8
• Product Categories: Aromatic Phenols;The group of Magnolia;Antifungal;Nutritional Ingredients;Plant extract;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors;Honokiol
• Mol File: 528-43-8.mol

Chemical Properties

• Melting Point: 101.5-102°
• Boiling Point: 180°C/1mmHg(lit.)
• Flash Point: 184.5 °C
• Appearance: /
• Density: 1.107 g/cm³
• Vapor Pressure: 5.25E-07mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble1mg/mL
• PKA: 9.49±0.43(Predicted)
• Merck: 14,5697
• CAS DataBase Reference: Magnolol(CAS DataBase Reference)
• NIST Chemistry Reference: Magnolol(528-43-8)
• EPA Substance Registry System: Magnolol(528-43-8)

Safety Data

• Hazard Codes: N
• Statements: 37/38-41-51/53
• Safety Statements: 26-39-61
• RIDADR: UN 3077
• WGK Germany: 3
• RTECS: DV5105500
• Hazardous Substances Data: 528-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Magnolol is used as a therapeutic agent for the treatment of anxiety, sleep disorders, and allergic diseases due to its ability to act on the GABA receptor and activate cannabinoid (CB) receptors.
Used in Dental Industry:
Magnolol is used as an antifungal and anti-periodontal agent for oral health care, thanks to its antifungal and anti-periodontal activities.
Used in Orthopedic Industry:
Magnolol is used to stimulate osteoblast activity and inhibit osteoclast activity, making it a potential candidate for bone health and treatment of related conditions.
Used in Cosmetics Industry:
Magnolol can be used as an active ingredient in cosmetics for its antifungal and anti-inflammatory properties, which may be beneficial for skin health and treatment of certain skin conditions.

References

https://en.wikipedia.org/wiki/Magnolol https://www.caymanchem.com/product/14233

Hazard

Moderately toxic by ingestion.

Biological Activity

Magnolol, a natural lignan isolated from the stem bark of Magnolia officinalis, is a dual agonist of both RXRα and PPARγ, with EC50 values of 10.4 μM and 17.7 μM, respectively.

Mechanism of action

Magnolol (5,5’-diallyl-2,2’-dihydroxybiphenyl) is a polyphenolic binaphthalene compound and a structural isomer of honokiol. Both magnolol and honokiol are isolated from the stem bark of a traditional Chinese herbal medicine Magnolia officinalis, which has been used for management of nervous disturbance, abdominal distention or disorders, gastrointestinal food stagnancy, and coughing and dyspnea. Magnolol has showed a wide spectrum of beneficial activities, including anti-inflammation, antimicroorganism, antioxidation, antiangiogenesis, anticancer, neuroprotection, cardiovascular protection, and lipolysis activities.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits acrid smoke andirritating vapors.

in vitro

Magnolol is a bioactive lignin found in the bark of the Houpu magnolia (Magnolia officinalis) which shows antifungal properties. Magnolol preferentially increases (3)H-muscimol binding to hippocampus compared to cortex and cerebellum in vitro. Magnolol has a more potent enhancing effect on GABAA receptor alpha2 subunit. Magnolol shows significant inhibitory activities against Trichophyton mentagrophytes, Microsporium gypseum, Epidermophyton floccosum, Aspergillus niger, Cryptococcus neoformans, and Candida albicans with minimum inhibitory concentrations (MIC) in a range of 25-100 μg/ml.

in vivo

Magnolol (5-15 mg/kg, p.o.) significantly attenuates the phenotypic severity of dextran sulfate sodium (DSS)-induced colitis in mice. Magnolol (10, 15 mg/kg, p.o.) attenuates histopathological changes and myeloperoxidase activity in the colon of DSS-treated mice, decreases DSS-induced high levels of proinflammatory cytokines TNF-α, IL-1β and IL-6 in the colonic tissues. Magnolol (10 mg/kg, p.o.) also reverses abnormality of serum metabolome, and regulates tryptophan metabolic pathway in mice.

InChI:InChI=1/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2

Synthetic route

5,5'-Diallyl-2,2'-bis(methoxymethoxy)biphenyl → Magnolol (528-43-8)

Conditions	Yield
With chloro-trimethyl-silane In methanol at 0 - 25℃; for 1h;	90%
With chloro-trimethyl-silane In methanol at 0 - 25℃; for 1h;	90%
With hydrogenchloride In tetrahydrofuran; isopropyl alcohol for 18h; Ambient temperature;	70%

2,2′-di(allyloxy)-biphenyl (73429-23-9) → Magnolol (528-43-8)

Conditions	Yield
With antimonypentachloride In dichloromethane at -78℃;	81%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8)

Conditions	Yield
With aluminium trichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In nitromethane for 1.5h; Ambient temperature;	77%
With air; ethanol; iron(III) chloride

5,5'-diallyl-2,2'-dimethoxy-1,1'-biphenyl (68592-16-5) → Magnolol (528-43-8)

Conditions	Yield
With boron tribromide In dichloromethane at -78℃; for 1h;	75%
With aluminum (III) chloride; thiourea In 1,2-dichloro-ethane at 50℃;
With aluminum (III) chloride; thiourea In 1,2-dichloro-ethane at 50℃;

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8) + isomagnolol

Conditions	Yield
With horseradish peroxidase type-1; dihydrogen peroxide In methanol at 20℃; for 0.3h; pH=6.0;	A 28% B 5%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8) + dunnianol (139726-29-7) + isomagnolol

Conditions	Yield
With air; iron(III) chloride In ethanol for 48h;	A 15% B 2% C 1%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8) + dunnianol (139726-29-7) + 8,9b-diallyl-4a,9b-dihydro-4H-dibenzofuran-3-one + isomagnolol

Conditions	Yield
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given;	A 8% B 11% C 12% D 5%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8) + dunnianol (139726-29-7) + 8,9b-diallyl-4a,9b-dihydro-4H-dibenzofuran-3-one + 8,9b-diallyl-2-(4-allyl-phenoxy)-4a,9b-dihydro-4H-dibenzofuran-3-one

Conditions	Yield
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given;	A 8% B 11% C 12% D 5%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8) + dunnianol (139726-29-7) + 8,9b-diallyl-4a,9b-dihydro-4H-dibenzofuran-3-one + 5,5',5'',5'''-tetraallyl-[1,3';1',1'';3'',1''']quaterphenyl-2,2',2'',2'''-tetraol

Conditions	Yield
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given;	A 8% B 11% C 12% D 4%

methyl magnesium iodide (917-64-6) + 5,5'-diallyl-2,2'-dimethoxy-1,1'-biphenyl (68592-16-5) → Magnolol (528-43-8)

Conditions	Yield
at 180℃;

methanol (67-56-1) + 1-oxaspiro[4,5]deca-6,9-dien-2,8-dione (4572-26-3) + p-cresol (106-44-5) → Magnolol (528-43-8) + 2,2'-dihydroxy-5-methyl-5'-(2-methoxycarbonylethyl)biphenyl (112639-25-5)

Conditions	Yield
With sulfuric acid; tin(IV) chloride 1.) MeNO2, 2 min; 2.) reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

eudesmagnolol (126654-54-4) → Magnolol (528-43-8) + cryptomeridiol (60132-35-6, 92857-25-5, 108006-39-9, 122674-21-9, 143004-65-3, 4666-84-6)

Conditions	Yield
With trifluoroacetic acid In benzene

eudesmagnolol (126654-54-4) → Magnolol (528-43-8) + eudesm-4-en-11-ol (13902-07-3, 15051-81-7, 72173-98-9, 98683-12-6, 117066-77-0, 1209-71-8)

Conditions	Yield
With trifluoroacetic acid In benzene for 10h; Ambient temperature;	A 12 mg B 3 mg
With trifluoroacetic acid In benzene for 10h; Ambient temperature;	A 12 mg B 2 mg

Magnolol glucuronide (102141-20-8) → D-glucuronic acid (6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7) + Magnolol (528-43-8)

Conditions	Yield
With β-glucuronidase-arylsulfatase In various solvent(s) at 37℃; for 4h; Product distribution;

Estragole (140-67-0) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / BBr3; Me2S / Heating 2: 28 percent / horseradish peroxidase type-1; aq. H2O2 / methanol / 0.3 h / 20 °C / pH 6.0 View Scheme

4-bromo-phenol (106-41-2) + isobutyl halide → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 3: 3N aq. HCl / tetrahydrofuran / 3 h / Heating 4: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme

p-methoxymethoxybromobenzene (25458-45-1) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 2: 3N aq. HCl / tetrahydrofuran / 3 h / Heating 3: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme

1-allyl-4-(methoxymethoxy)benzene (70482-71-2) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3N aq. HCl / tetrahydrofuran / 3 h / Heating 2: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme

2,2'-dimethoxy-5,5'-dibromo-biphenyl (100542-54-9) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: THF / anschliessend Erwaermen mit Allylbromid 2: 180 °C View Scheme

2,2'-dihydroxybiphenyl (1806-29-7) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: bromine / chloroform / 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0 °C 3.1: ethyl bromide; magnesium / tetrahydrofuran / Inert atmosphere; Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide 2: bromine 3: tetrahydrofuran 4: thiourea; aluminum (III) chloride / 1,2-dichloro-ethane / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: bromine / chloroform / 2 h 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0 °C 3.1: magnesium; ethyl bromide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 3.2: 3 h / 0 - 20 °C / Inert atmosphere 4.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme

5,5'-dibromo-2,2'-dihydroxybiphenyl (34261-55-7) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 1.2: 0 °C 2.1: ethyl bromide; magnesium / tetrahydrofuran / Inert atmosphere; Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 1.2: 0 °C 2.1: magnesium; ethyl bromide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 0 - 20 °C / Inert atmosphere 3.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme

2,2'-Dimethoxybiphenyl (4877-93-4) → Magnolol (528-43-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine 2: tetrahydrofuran 3: thiourea; aluminum (III) chloride / 1,2-dichloro-ethane / 50 °C View Scheme

ethyl bromide (74-96-4) + Magnolol (528-43-8) → 2’-ethoxy-5,5’-di(prop-2-en-1-yl)biphenyl-2-ol (1356708-23-0)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 48h;	98%

Magnolol (528-43-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 5,5'-diallyl-2′-((tert-butyldimethylsilyl)oxy)-[1,1′-biphenyl]-2-ol

Conditions	Yield
With 1H-imidazole In dichloromethane at 22℃; for 1h; Inert atmosphere;	98%
With 1H-imidazole In dichloromethane at 20℃; for 3h;	96%

Magnolol (528-43-8) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → (S)-5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(6-methoxynaphthalen-2-yl)propanoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	97%

Magnolol (528-43-8) + naproxen (23981-80-8) → C32H30O4

Conditions	Yield
With dmap In dichloromethane at 25 - 30℃;	97%

Magnolol (528-43-8) + methyl iodide (74-88-4) → 2-O-methylmagnolol (87980-21-0)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 17h;	96%
With 18-crown-6 ether; potassium carbonate In acetone for 17h; Product distribution / selectivity;

diazomethane (186581-53-3, 908094-01-9) + Magnolol (528-43-8) → 2-O-methylmagnolol (87980-21-0)

Conditions	Yield
In diethyl ether for 24h;	95%
In diethyl ether for 24h; Product distribution / selectivity;	95%
In diethyl ether Ambient temperature;

Magnolol (528-43-8) + 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid (22494-42-4) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	95%

2',4'-difluoro-3-hydroxybiphenyl-4-carboxylic acid (615557-17-0) + Magnolol (528-43-8) → C31H24F2O4

Conditions	Yield
With dmap In dichloromethane at 25 - 30℃;	95%

formaldehyd (50-00-0) + Magnolol (528-43-8) + N-butylamine (109-73-9) → C30H40N2O2

Conditions	Yield
In 1,4-dioxane; toluene at 90℃; for 72h;	94.5%

Magnolol (528-43-8) + chloromethyl methyl ether (107-30-2) → C20H22O3

Conditions	Yield
With triethylamine In dichloromethane at 22℃; for 2h;	94%

Magnolol (528-43-8) + salicylic acid (69-72-7) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-hydroxybenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	93%
With dmap In dichloromethane at 25 - 30℃;	92%

Magnolol (528-43-8) + tolfenamic Acid (13710-19-5) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-((3-chloro-2-methylphenyl)amino)benzoate

Conditions	Yield
With dmap In dichloromethane at 25 - 30℃;	93%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	92%

Magnolol (528-43-8) + mefenamic Acid (61-68-7) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-((2,3-dimethylphenyl)amino)benzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	92%
With dmap In dichloromethane at 25 - 30℃;	92%

Magnolol (528-43-8) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(2-((2,6-dichlorophenyl)amino)phenyl) acetate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	92%
With dmap In dichloromethane at 25 - 30℃;	92%

Magnolol (528-43-8) + butyryl chloride (141-75-3) → C26H30O4 + C22H24O3

Conditions	Yield
Stage #1: Magnolol With potassium carbonate In acetone for 0.5h; Inert atmosphere; Reflux; Stage #2: butyryl chloride In acetone for 24h; Reflux;	A 92% B 8%

formaldehyd (50-00-0) + furan-2-ylmethanamine (617-89-0) + Magnolol (528-43-8) → C32H32N2O4

Conditions	Yield
In 1,4-dioxane; toluene at 90℃; for 32h;	91.5%

Magnolol (528-43-8) + flufenamic acid (530-78-9) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-((3-(trifluoromethyl)phenyl)amino)benzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	91%
With dmap In dichloromethane at 25 - 30℃;	91%

Magnolol (528-43-8) + ibuprofen (15687-27-1) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(4-isobutylphenyl)propanoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	91%
With dmap In dichloromethane at 25 - 30℃;	91%

Magnolol (528-43-8) + acetic anhydride (108-24-7) → magnolol monoacetate

Conditions	Yield
Stage #1: Magnolol With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Stage #2: acetic anhydride In acetone at 20℃; for 1h;	90%
In pyridine

Magnolol (528-43-8) + etodolac (41340-25-4) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	90%
With dmap In dichloromethane at 25 - 30℃;	90%

Magnolol (528-43-8) + ethylene dibromide (106-93-4) → 5,5'-diallyl-2’-(2-bromoethoxy)-[1,1'-biphenyl]-2-ol

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 6h;	90%
With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 3h;	65%

Magnolol (528-43-8) → C18H21N

Conditions	Yield
With ammonium hydroxide; 10 wt% Pd(OH)2 on carbon; sodium formate; trifluoroacetic acid In m-xylene at 140℃; for 24h; Inert atmosphere;	90%

4-Nitrophthalonitrile (31643-49-9) + Magnolol (528-43-8) → C34H22N4O2

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 40℃; for 48h; Inert atmosphere;	90%

Magnolol (528-43-8) + Diphenylphosphinic chloride (1499-21-4) → C42H36O6P2

Conditions	Yield
Stage #1: Magnolol With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice; Inert atmosphere; Stage #2: Diphenylphosphinic chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #3: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	89%

Magnolol (528-43-8) + benzoic acid (65-85-0) → 4'-di-O-benzoyl-magnolol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	88.15%

Magnolol (528-43-8) + ketoprofen (22071-15-4) → 5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(3-benzoylphenyl)propanoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;	88%

ethyl 2-phenyldiazoacetate (22065-57-2) + Magnolol (528-43-8) → ethyl 2-((5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)-2-phenylacetate

Conditions	Yield
Stage #1: ethyl 2-phenyldiazoacetate; Magnolol In 1,2-dichloro-ethane at 20℃; for 0.0333333h; Schlenk technique; Green chemistry; Stage #2: With trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 0.333333h; Schlenk technique; Green chemistry;	88%
With sewage sludge-derived carbon material treated with perchloric acid In 1,2-dichloro-ethane at 70℃; for 24h;	86%
With sewage sludge-derived carbonaceous materials treated by perchloric acid; air In 1,2-dichloro-ethane at 20 - 70℃; under 750.075 Torr; for 5h; Solvent; Schlenk technique;	85%

Magnolol (528-43-8) + Cinnamic acid (621-82-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → magnolol-4-O-cinnamyl-4'-O- β-D-glucopyranoside

Conditions	Yield
Stage #1: Magnolol With sodium hydroxide In water for 0.5h; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 3.5h; Stage #3: Cinnamic acid Further stages;	87.2%

Magnolol (528-43-8) + benzoic acid (65-85-0) → 4'-O-benzoylmagnolol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	86.74%

Upstream product

• 917-64-6 methyl magnesium iodide 
• 68592-16-5 5,5'-diallyl-2,2'-dimethoxy-1,1'-biphenyl 
• 501-92-8 4-(prop-2-enyl)phenol 
• 67-56-1 methanol 
• 4572-26-3 1-oxaspiro[4,5]deca-6,9-dien-2,8-dione 
• 106-44-5 p-cresol 
• 126654-54-4 eudesmagnolol 
• 102141-20-8 Magnolol glucuronide 
• 140-67-0 Estragole 
• 106-41-2 4-bromo-phenol 
• 25458-45-1 p-methoxymethoxybromobenzene 
• 70482-71-2 1-allyl-4-(methoxymethoxy)benzene 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 34261-55-7 5,5'-dibromo-2,2'-dihydroxybiphenyl 

Downstream Products

• 130756-35-3 clovanemagnolol 
• 93673-81-5 magnolignan A 
• 133056-11-8 caryolanemagnolol 

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Six products have been isolated from the oxidative coupling of 4-allylphenol in the presence of FeIII; the distribution of products suggests that oligomeric neolignans associated with the family Illicium may also be non-enzymic products of oxidative coupling.

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Synthesis method of magnolol

The invention relates to a synthesis method of magnolol. The synthesis method comprises the following steps: (1) performing reaction on 1,1'-biphenyl-2,2'-diphenol serving as a raw material and allylhalide under the existence of alkali to prepare 2,2'-diallyl-1,1'-biphenyl; (2) dissolving the 2,2'-diallyl-1,1'-biphenyl into a solvent and performing rearrangement reaction under the existence of columbium pentachloride to obtain the magnolol. Compared with the conventional reaction system, the synthesis method has the characteristics of simple route, simplicity and convenience in operation, mild condition and the like.

SYNTHESIS OF MAGNOLOL AND ITS ANALOGUE COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method for producing a magnolol, or a derivative or analogue thereof, which is applied to compositions for treating bacteria and/or inflammation related oral diseases. SOLUTION: A method for producing a magnolol in the figure or a derivative of the magnolol comprises brominating and converting 2,2'-bisphenol to 5,5'-dibromo-2,2'-bisphenol, protecting hydroxyl groups by reaction with methoxymethyl chloride; further reacting it with magnesium, an allyl bromide or a substituted allyl bromide; and then deprotecting it. (R is H, alkyl, or substituted or unsubstituted phenyl.) COPYRIGHT: (C)2015,JPOandINPIT

PROCESSES FOR MAKING MAGNOLOL AND DERIVATIVES THEREOF

Described herein are high yield methods for making magnolol (5,5′-diallyl-biphenyl-2,2′-diol) and tetrahydro-magnolol (5,5′-dipropyl-biphenyl-2,2′-diol).

PROCESSES FOR MAKING MAGNOLOL AND DERIVATIVES THEREOF

Described herein are high yield methods for making magnolol (5,5'-diallyl-biphenyl-2,2'-diol) and tetrahydromagnolol (5,5'-dipropyl-biphenyl-2,2'-diol).

SYNTHESIS OF MAGNOLOL AND ITS ANALOGUE COMPOUNDS

A method is described for producing magnolol, or a derivative or analogue thereof. The method includes obtaining MOM ether of 5,5'-diallylbiphenyl-2,2'-diol or a derivative or analogue thereof and subsequently converting the MOM ether of 5,5'-diallylbiphenyl-2,2'-diol into magnolol or a derivative or analogue thereof.

Cytotoxic neolignans: An SAR study

The cytotoxic effects of different neolignans with the structure 1 were studied. The neolignans, magnolol 1 and honokiol 2 have been reported to inhibit the growth of several tumor cell lines in vitro and in vivo. The chemical structure of magnolol and honokiol consists of biphenyl skeleton with phenolic and allylic functionalities. Analogs of 1 and 2 containing different substitution have been studies for their effect on the growth of Hep-G2 and their structure-activity relationships were reported in this work.

Enantioselective syntheses of (S)- and (R)-8,9 dihydroxydihydromagnolol

8,9-Dihydroxydihydromagnolol 5 was synthesized in four steps in which the synthesis of magnolol 4 was improved and the absolute configuration of 5 was confirmed as (R).

Synthesis of (-)-Monoterpenylmagnolol and Magnolol

(-)-Monoterpenylmagnolol (3) was synthesized in eight steps from (+)-3,9-dibromocamphor (4) and the bis(methoxymethyl) ether (22) of 3-(4-hydroxyphenyl)-1-propanol.Fragmentation of an endo-3-aryl-9-bromocamphor (27) provided the correct absolute stereochemistry.In this total synthesis, dissolving metal conditions were developed to reduce enol phosphate and isopropenyl functions without concomitant reduction of an attached phenol.Palladium(0)-catalyzed cross-coupling of an arylzinc chloride with 4-allyl-2-iodophenyl methoxymethyl ether (34) provided the desired tricyclic 1,2,3,5-tetrasubstituted biaryl 41 in fair yield without optimization and with little isomerization of the allyl group.Magnolol (1) was also synthesized by aryl coupling of 34 and the methoxymethyl ether of 4-allyl-2-lithiophenol via the zinc chloride method as above, as well as from 5,5'-dibromo-2,2'-dimethoxybiphenyl (37) by allylation with allyltributylstannane followed by ether cleavage.