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533-31-3

Basic Information
CAS No.: 533-31-3
Name: Sesamol
Article Data: 72
Molecular Structure:
Molecular Structure of 533-31-3 (Sesamol)
Formula: C7H6O3
Molecular Weight: 138.123
Synonyms: Phenol,3,4-(methylenedioxy)- (7CI,8CI);3,4-(Methylenedioxy)phenol;4-Hydroxy-1,2-methylenedioxybenzene;5-Hydroxy-1,3-benzodioxole;Benzodioxol-5-ol;NSC 59256;3,4-Methylenedioxyphenol (Sesamol);
EINECS: 208-561-5
Density: 1.394 g/cm3
Melting Point: 62-65 °C(lit.)
Boiling Point: 274 °C at 760 mmHg
Flash Point: 119.5 °C
Solubility: slightly soluble in water
Appearance: white to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 38.69000
LogP: 1.12090
Synthetic route
5876-51-7

5-iodo-1,3-benzodioxole

533-31-3

Sesamol

Conditions
ConditionsYield
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%
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

533-31-3

Sesamol

Conditions
ConditionsYield
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%
120-57-0

piperonal

533-31-3

Sesamol

Conditions
ConditionsYield
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%
16387-85-2

benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate

533-31-3

Sesamol

Conditions
ConditionsYield
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%
326-58-9

acetic acid benzo[1,3]dioxol-5-yl ester

533-31-3

Sesamol

Conditions
ConditionsYield
With water; potassium hydroxide In methanol at 50℃; for 2h;95%
With water at 20℃; for 1.25h;95%

sodium 1,3-benzodioxol-5-olate

533-31-3

Sesamol

Conditions
ConditionsYield
With hydrogenchloride In water pH=8.5;94.3%
87770-73-8

5-(2-Methoxy-ethoxymethoxy)-benzo[1,3]dioxole

533-31-3

Sesamol

Conditions
ConditionsYield
With 2-chloro-1,3,2-dithioborolane In dichloromethane at -78℃; for 0.75h;94%
112579-46-1

5-propionyloxy-benzo[1,3]dioxole

533-31-3

Sesamol

Conditions
ConditionsYield
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%
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

533-31-3

Sesamol

Conditions
ConditionsYield
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

5-(4-methoxy-benzyloxy)-benzo[1,3]dioxole

533-31-3

Sesamol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 5h; ether cleavage; Heating;91%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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.
5. Safety Information of Sesamol
Questionable carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany 3
RTECS SM0890000
Hazard Note Irritant
HS Code 29329970

6. Use of Sesamol
Sesamol is used as antioxidants, pharmaceutical intermediates and cosmetic additives.Or as an antioxidant that may prevent the spoilage of oils. It is also used in Ayur-Vedic Medicine.

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