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524-12-9

Basic Information
CAS No.: 524-12-9
Name: WEDELOLACTONE
Article Data: 9
Molecular Structure:
Molecular Structure of 524-12-9 (WEDELOLACTONE)
Formula: C16H10O7
Molecular Weight: 314.251
Synonyms: Wedelolactone;
EINECS: 200-158-5
Density: 1.655 g/cm3
Melting Point: 327~330℃
Boiling Point: 498.4 °C at 760 mmHg
Flash Point: 255.2 °C
Solubility: DMSO: 14 mg/mL, soluble
Appearance: brown-beige solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-43
Safety: 36/37
PSA: 113.27000
LogP: 2.81780
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogen iodide
5447-02-9

3,4-dibenzyloxybenzaldehyde

524-12-9

wedelolactone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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    WEDELOLACTONE

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    524-12-9

    Wedelolactone

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    Wedelolactone

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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