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Name	Wedelolactone	EINECS	200-158-5
CAS No.	524-12-9	Density	1.655 g/cm³
PSA	113.27000	LogP	2.81780
Solubility	DMSO: 14 mg/mL, soluble	Melting Point	327～330℃
Formula	C₁₆H₁₀O₇	Boiling Point	498.4 °C at 760 mmHg
Molecular Weight	314.251	Flash Point	255.2 °C
Transport Information	N/A	Appearance	brown-beige solid
Safety	36/37	Risk Codes	22-43
Molecular Structure		Hazard Symbols	Xn
Synonyms	Wedelolactone;	Article Data	9

Wedelolactone Synthetic route

: 627489-05-8
2-(2,6-dihydroxy-4-methoxy-phenyl)-5,6-dihydroxy-benzofuran-3-carboxylic acid methyl ester

: 524-12-9
wedelolactone

Conditions

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

: 1023744-97-9
1-hydroxy-3-methoxy-8,9-diisopropyloxy-benzo[4,5]furo[3,2-c]chromen-6-one

: 524-12-9
wedelolactone

Conditions

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

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

: 524-12-9
wedelolactone

Conditions

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%

: 67964-24-3
4,5-dihydroxy-7-methoxy coumarin

: 120-80-9
benzene-1,2-diol

: 524-12-9
wedelolactone

Conditions

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: tri-O-methyl-wedelolactone

: 524-12-9
wedelolactone

Conditions

Conditions	Yield
With hydrogen iodide

: 5447-02-9
3,4-dibenzyloxybenzaldehyde

: 524-12-9
wedelolactone

Conditions

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

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

: 27688-86-4
3,4-dibenzyloxyphenol

: 524-12-9
wedelolactone

Conditions

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

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

: 27688-85-3
3,4-Dibenzyloxyphenyl-acetat

: 524-12-9
wedelolactone

Conditions

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

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

: 91360-58-6
2,6-bis(benzyloxy)-4-methoxybenzaldehyde

: 524-12-9
wedelolactone

Conditions

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

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

: 139-85-5
3,4-dihydroxybenzaldehyde

: 524-12-9
wedelolactone

Conditions

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

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

Wedelolactone Specification

The CAS register number of Wedelolactone is 524-12-9. It also can be called as 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy- and the IUPAC name about this chemical is 1,8,9-trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one. The molecular formula about this chemical is C₁₆H₁₀O₇ and the molecular weight is 314.25. This chemical is a antihepatotoxic coumestan from Eclipta prostrata and Wedelia calendulacea (both Asteraceae).

Physical properties about Wedelolactone are: (1)ACD/LogP: 2.75; (2)ACD/LogD (pH 5.5): 2.75; (3)ACD/LogD (pH 7.4): 2.45; (4)ACD/BCF (pH 5.5): 71.87; (5)ACD/BCF (pH 7.4): 36.36; (6)ACD/KOC (pH 5.5): 739.81; (7)ACD/KOC (pH 7.4): 374.29; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 76.36Å²; (12)Index of Refraction: 1.758; (13)Molar Refractivity: 77.99 cm³; (14)Molar Volume: 189.8 cm³; (15)Polarizability: 30.92x10^-24cm³; (16)Surface Tension: 83.8 dyne/cm; (17)Enthalpy of Vaporization: 79.57 kJ/mol; (18)Boiling Point: 498.4 °C at 760 mmHg; (19)Vapour Pressure: 1.48E-10 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,8,9-tris-benzyloxy-3-methoxy-benzo[4,5]furo[3,2-c]chromen-6-one. This reaction will need reagent hydrogen, catalyst Pd(C) and solvent dioxane. The objective of this reaction is product distribution. This reaction also needs 2nd step of purification of 9 (wedelolactone). The yield is about 82%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and it may cause sensitization by skin contact. When you are using it, wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C3Oc4cc(OC)cc(O)c4c2oc1c(cc(O)c(O)c1)c23
(2)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
(3)InChIKey: XQDCKJKKMFWXGB-UHFFFAOYAT
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: XQDCKJKKMFWXGB-UHFFFAOYSA-N

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