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
• Article Data: 14

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

Description

Different sources of media describe the Description of 528-43-8 differently. You can refer to the following data:
1. Magnolol is an organic compound belonging to lignan. It is a kind of bioactive compounds identified from the bark of the Magnolia officinalis or M. grandiflora. It has been supplemented to Asian traditional medicine for the treatment of anxiety, sleep disorders, and allergic disease. It can act on the GABA receptor in vitro as a strong allosteric modulator. It also has antifungal effect, anti- periodontal activity as well as many osteoblast-stimulating and osteoclast-inhibiting activities. It has also found that magnolol can also activate the cannabinoid (CB) receptors.
2. Magnolol is a bioactive compound isolated from the bark of M. officinalis that has been used in Asian traditional medicine for the treatment of anxiety, sleep disorders, and allergic diseases. Magnolol can activate cannabinoid (CB) receptors, behaving as a partial agonist with selectivity for the peripheral CB2 subtype (EC50 = 3.28 μM; Ki = 1.44 μM) versus central CB1 (EC50 = 18.3 μM; Ki = 3.15 μM).

References

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

Chemical Properties

White or off-white powder

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 
• 73429-23-9 2,2′-di(allyloxy)-biphenyl 
• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 34261-55-7 5,5'-dibromo-2,2'-dihydroxybiphenyl 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 100542-54-9 5,5'-dibromo-2,2'-dimethoxy-biphenyl 
• 70482-71-2 1-allyl-4-(methoxymethoxy)benzene 
• 25458-45-1 p-methoxymethoxybromobenzene 

Downstream Products

• 20601-85-8 tetrahydromagnolol 
• 87979-85-9 trans-Isomagnolol 
• 130756-35-3 clovanemagnolol 
• 93673-81-5 magnolignan A 
• 132-64-9 dibenzofuran 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 140866-37-1 magnolignan A 

Relevant articles and documents

Biomimetic Synthesis of Illicium Oligomeric Neolignans

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.

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.

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).