524-12-9

Basic information

• Product Name: WEDELOLACTONE
• Synonyms: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one;Wedelolactone;6H-Benzofuro(3,2-C)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy-;5,11,12-Trihydroxy-7-MethoxycouMestan;1,8,9-trihydroxy-3-Methoxy-6H-benzofuro[3,2-c]chroMen-6-one;Wedelia lactone;IKK Inhibitor II, Wedelolactone;Wedelolactone, 98%, from Wedelia chinensis (Osbeck.) Merr.
• CAS NO: 524-12-9
• Molecular Formula: C₁₆H₁₀O₇
• Molecular Weight: 314.25
• EINECS: 200-158-5
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 524-12-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 327～330℃
• Boiling Point: 498.4 °C at 760 mmHg
• Flash Point: 255.2 °C
• Appearance: brown-beige/solid
• Density: 1.655 g/cm³
• Vapor Pressure: 1.48E-10mmHg at 25°C
• Refractive Index: 1.758
• Storage Temp.: 2-8°C
• Solubility: DMSO: 14 mg/mL, soluble
• PKA: 6.90±0.20(Predicted)
• CAS DataBase Reference: WEDELOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: WEDELOLACTONE(524-12-9)
• EPA Substance Registry System: WEDELOLACTONE(524-12-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 524-12-9(Hazardous Substances Data)

Usage

Uses

Wedelolactone is inhibits caspase-11; a key regulator of proinflammatory cytokine IL-1β maturation and apoptosis.

Definition

ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3.

Biological Activity

wedelolactone is an inhibitor of ikk.ikb kinase (ikk) complex contains the catalytic subunits ikkα and ikkβ, and the regulatory subunit ikkγ/nemo. ikk, is a kinase critical for activation of nf-κb by mediating phosphorylation and degradation of iκbα. the induction of caspase-11 is an important upstream controlling event in inflammatory response and apoptosis under pathological conditions modulated by upstream nf-κb-mediated transcription[1].

Biochem/physiol Actions

Wedelolactone inhibits NF-κB-mediated gene transcription in cells by blocking the phosphorylation and degradation of IκBα. Irreversible inhibitor of IKKα and β kinase activity (IC50 < 10 μM). Wedelolactone has no effects on p38 MAP kinase or Akt.

in vitro

in cultured mouse balb/c 3t3 cells, mouse splenocytes and hela cells, wedelolactone (0~100 μm) inhibited lps-induced caspase-11 expression by inhibiting nf-κb-mediated transcription through the direct inhibition of ikk. wedelolactone played an potential role in anti-inflammatory therapy to inhibit il-1β levels in diseases such as rheumatoid arthritis, asthma and septic shock[1].

in vivo

on swiss albino male mouse skin, ikk inhibition by wedelolactone (10 μm) prevented the induction of nf-κb, perturbed the generation of reactive oxygen species and reactive nitrogen intermediates, blunted the signal transduction that lead to the activation of the early immediate genes, and thereby protected mouse skin from the uvb induced neoplastic transformation, angiotropism and metastatic progression [2].

references

[1] kobori m, yang z, gong d, et al. wedelolactone suppresses lps-induced caspase-11 expression by directly inhibiting the ikk complex.[j]. cell death & differentiation, 2004, 11(1):123-30.[2] ali f, khan b a, sultana s. wedelolactone mitigates uvb induced oxidative stress, inflammation and early tumor promotion events in murine skin: plausible role of nfκb pathway[j]. european journal of pharmacology, 2016, 786:253-264.

InChI:InChI=1/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

Synthetic route

2-(2,6-dihydroxy-4-methoxy-phenyl)-5,6-dihydroxy-benzofuran-3-carboxylic acid methyl ester (627489-05-8) → wedelolactone (524-12-9)

Conditions	Yield
With sulfuric acid; acetic acid In water at 50℃; for 1h;	93%

1-hydroxy-3-methoxy-8,9-diisopropyloxy-benzo[4,5]furo[3,2-c]chromen-6-one (1023744-97-9) → wedelolactone (524-12-9)

Conditions	Yield
With boron trichloride In dichloromethane at 0℃;	87%

1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (115623-32-0) → wedelolactone (524-12-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 1,4-dioxane Product distribution; 2nd step of purification of 9 (wedelolactone);	82%
With boron trichloride In dichloromethane at 0℃; Inert atmosphere;	81%

4,5-dihydroxy-7-methoxy coumarin (67964-24-3) + benzene-1,2-diol (120-80-9) → wedelolactone (524-12-9)

Conditions	Yield
With sodium acetate; potassium hexacyanoferrate(III) In water; acetone for 2h; Ambient temperature;	25%
With ascorbic acid 1.) tyrosinase, pH=6.8, r.t., 1 h; Yield given. Multistep reaction;

tri-O-methyl-wedelolactone → wedelolactone (524-12-9)

Conditions	Yield
With hydrogen iodide

3,4-dibenzyloxybenzaldehyde (5447-02-9) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 1.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 2.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 3.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 5.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 6.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 7.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 8.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme
Multi-step reaction with 8 steps 1.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 1.2: 0.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 20 °C 3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 4.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

3,4-dibenzyloxyphenol (27688-86-4) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 7 steps 1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 2: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 3: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 4: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 5: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 6: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 7: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 3.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 7.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

3,4-Dibenzyloxyphenyl-acetat (27688-85-3) → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 2: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

2,6-bis(benzyloxy)-4-methoxybenzaldehyde (91360-58-6) → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: t-BuOK / tetrahydrofuran / 0.5 h / 0 °C 1.2: 75 percent / t-BuOK / tetrahydrofuran / 0 - 25 °C 2.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

3,4-dihydroxybenzaldehyde (139-85-5) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 94 percent / K2CO3; n-Bu4NI / acetone / 24 h / Heating 2.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 2.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 3.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 4.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 5.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 6.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 7.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 8.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 9.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme
Multi-step reaction with 9 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 2.2: 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 20 °C 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 5.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 9.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

1,3-Bis-benzyloxy-2-ethynyl-5-methoxy-benzene (627489-10-5) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

acetic acid 4,5-bis-benzyloxy-2-iodo-phenyl ester (627489-15-0) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

4,5-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenylethynyl)-phenol (344303-12-4) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 2: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 3: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

acetic acid 4,5-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenylethynyl)-phenyl ester (627489-61-6) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 2: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 3: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 4: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

5,6-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenyl)-benzofuran-3-carboxylic acid methyl ester (344303-15-7) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 2: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

3,5-dihydroxyphenol (108-73-6) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / diethyl ether / 2 h 2: hydrogenchloride / 1 h / Heating 3: sodium carbonate / water / 1 h / 80 °C 4: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h View Scheme
Multi-step reaction with 8 steps 1.1: zinc(II) chloride / 2 h / 100 °C 2.1: potassium carbonate / acetone / 1 h / 90 °C 2.2: 1.5 h / 90 °C 3.1: bromine / dichloromethane / 8 h / 0 - 10 °C 3.2: 1 h / 20 °C 4.1: potassium carbonate / acetone / 56 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

4-amino-5,7-dihydroxycoumarin (162888-73-5) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / 1 h / Heating 2: sodium carbonate / water / 1 h / 80 °C 3: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h View Scheme

4,5,7-trihydroxycoumarin (17575-26-7) → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / water / 1 h / 80 °C 2: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h View Scheme

5-(benzyloxy)-3-(4,5-bis(benzyloxy)-2-((4-methoxybenzyl)oxy)phenyl)-7-methoxy-2-chromenone → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 2: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

C34H37BO6 → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

1,2-dibenzyloxy-4-(p-methoxybenzyl)oxybenzene → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

1,2-dibenzyloxy-4-bromo-5-(p-methoxybenzyl)oxybenzene → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

5,7-dihydroxy-2H-chromen-2-one (2732-18-5) → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: potassium carbonate / acetone / 1 h / 90 °C 1.2: 1.5 h / 90 °C 2.1: bromine / dichloromethane / 8 h / 0 - 10 °C 2.2: 1 h / 20 °C 3.1: potassium carbonate / acetone / 56 °C 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 7.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

5,7-diacetoxyl-2-chromenone (21524-17-4) → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: bromine / dichloromethane / 8 h / 0 - 10 °C 1.2: 1 h / 20 °C 2.1: potassium carbonate / acetone / 56 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4.1: potassium carbonate / N,N-dimethyl-formamide 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

3-bromo-5,7-diacetoxyl-2-chromenone (1023744-89-9) → wedelolactone (524-12-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 56 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

3-bromo-5-benzyloxy-7-acetoxyl-2-chromenone → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

5-(benzyloxy)-3-(4,5-bis(benzyloxy)-2-((4-methoxybenzyl)oxy)phenyl)-7-hydroxy-2-chromenone → wedelolactone (524-12-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 3: boron trichloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

wedelolactone (524-12-9) + benzyl chloride (100-44-7) → 1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (115623-32-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 0.833333h; Heating;	29%

wedelolactone (524-12-9) + acetyl chloride (75-36-5) → wedelolactone triacetate (6468-54-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 2h;

Upstream product

• 67964-24-3 4,5-dihydroxy-7-methoxy coumarin 
• 120-80-9 benzene-1,2-diol 
• 1023744-89-9 3-bromo-5,7-diacetoxyl-2-chromenone 
• 21524-17-4 5,7-diacetoxyl-2-chromenone 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 1023744-97-9 1-hydroxy-3-methoxy-8,9-diisopropyloxy-benzo[4,5]furo[3,2-c]chromen-6-one 
• 17575-26-7 4,5,7-trihydroxycoumarin 
• 162888-73-5 4-amino-5,7-dihydroxycoumarin 
• 108-73-6 3,5-dihydroxyphenol 
• 344303-15-7 5,6-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenyl)-benzofuran-3-carboxylic acid methyl ester 
• 627489-61-6 acetic acid 4,5-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenylethynyl)-phenyl ester 
• 344303-12-4 4,5-bis-benzyloxy-2-(2,6-bis-benzyloxy-4-methoxy-phenylethynyl)-phenol 
• 627489-15-0 acetic acid 4,5-bis-benzyloxy-2-iodo-phenyl ester 
• 627489-10-5 1,3-Bis-benzyloxy-2-ethynyl-5-methoxy-benzene 

Downstream Products

• 115623-32-0 1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one 

Relevant articles and documents

Palladium(II)-catalyzed efficient synthesis of wedelolactone and evaluation as potential tyrosinase inhibitor

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

Therapeutic drugs for arthritis

The present invention relates to the coumestans compounds extracted from Compositae plants, drug compositions or health products comprising the compounds and the use in treatment of rheumatic arthritis or rheumatoid arthritis, osteoarthritis. The animal experiments in vivo or in vitro indicate that the coumestans compounds can effectively treat and alleviate symptoms of rheumatic arthritis or rheumatoid arthritis, and osteoarthritis.

MUSHROOM TYROSINASE CATALYSED SYNTHESIS OF COUMENTANS, BENZOFURAN DERIVATIVES AND RELATED HETEROCYCLIC COMPOUNDS

Full details of an improved synthesis of coumestan derivatives and their structural analogues, viz., wedelolactone, 11-hydroxy aureol, 11-hydroxy coumestrol along benzofuran derivatives and related heterocyclic systems are reported by coupling of in situ generated o-quinones from catechols catalysed by mushroom tyrosinase with various reatants.