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Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 130℃; for 6h; | 59% |
With formic acid; oxygen; triethylamine; copper(ll) bromide In acetonitrile at 20℃; for 48h; Irradiation; | 52% |
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 120℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 72% |
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With oxaziridine In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
Stage #1: piperonal With 3-chloro-benzenecarboperoxoic acid for 0.0833333h; Dakin oxidation; Stage #2: With sodium hydroxide for 0.0833333h; Further stages.; | 95% |
With sulfuric acid; dihydrogen peroxide; boric acid In tetrahydrofuran; water at 20℃; for 3.5h; Oxidation; | 89% |
With sulfuric acid; dihydrogen peroxide; boric acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 0℃; Dakin reaction; | 78% |
benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate
Sesamol
Conditions | Yield |
---|---|
With magnesium In methanol for 4h; Ambient temperature; | 95% |
With potassium fluoride on basic alumina for 0.05h; Substitution; microwave irradiation; | 88% |
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; carbon dioxide; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation; | 31% |
Conditions | Yield |
---|---|
With water; potassium hydroxide In methanol at 50℃; for 2h; | 95% |
With water at 20℃; for 1.25h; | 95% |
Sesamol
Conditions | Yield |
---|---|
With hydrogenchloride In water pH=8.5; | 94.3% |
5-(2-Methoxy-ethoxymethoxy)-benzo[1,3]dioxole
Sesamol
Conditions | Yield |
---|---|
With 2-chloro-1,3,2-dithioborolane In dichloromethane at -78℃; for 0.75h; | 94% |
5-propionyloxy-benzo[1,3]dioxole
Sesamol
Conditions | Yield |
---|---|
Stage #1: 5-propionyloxy-benzo[1,3]dioxole With sodium hydroxide; tetrabutyl-ammonium chloride; water In dichloromethane at 20 - 25℃; for 8 - 8.75h; Stage #2: With hydrogenchloride In dichloromethane; water pH=8.5; | 92.3% |
3,4-(methylenedioxy)-benzeneboronic acid
Sesamol
Conditions | Yield |
---|---|
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique; | 92% |
With dihydrogen peroxide In water at 20℃; for 0.0833333h; | 92% |
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry; | 88% |
With rongalite In ethanol; water at 20℃; for 7h; Irradiation; | 71% |
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation; | 30 mg |
Sesamol
Conditions | Yield |
---|---|
With carbon tetrabromide In methanol for 5h; ether cleavage; Heating; | 91% |
Reported in EPA TSCA Inventory.
1. Introduction of Sesamol
Sesamol is a natural organic compound which is a component of sesame oil. It has been found to be an antioxidant that may prevent the spoilage of oils, and may protect the body from damage from free radicals. The IUPAC Name of it is 1,3-benzodioxol-5-ol.
2. Properties of Sesamol
Melting Point: 62-65 °C(lit.)
Boiling point: 274 °C at 760 mmHg
Storage Temperature: -20°C
Flash Point: 119.5 °C
Density: 1.394 g/cm3
Water Solubility: slightly soluble
Index of Refraction: 1.609
Molar Refractivity: 34.29 cm3
Molar Volume: 99 cm3
Surface Tension: 61.7 dyne/cm
Enthalpy of Vaporization: 53.3 kJ/mol
Vapour Pressure: 0.00331 mmHg at 25°C
XLogP3-AA: 1.2
H-Bond Donor: 1
H-Bond Acceptor: 3
3. Structure Descriptors of Sesamol
Canonical SMILES: C1OC2=C(O1)C=C(C=C2)O
InChI: InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChIKey: LUSZGTFNYDARNI-UHFFFAOYSA-N
4. Toxicity of Sesamol
1. | orl-mus TDLo:1092 g/kg/2Y-C:CAR | JJCREP Japanese Journal of Cancer Research (Gann). 83 (1992),1279. | ||
2. | orl-mus LD:1612 g/kg/96W-C:CAR | JJCREP Japanese Journal of Cancer Research (Gann). 81 (1990),207. |