Sesamol

Base Information

• Chemical Name: Sesamol
• CAS No.: 533-31-3
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 29329970
• European Community (EC) Number: 208-561-5
• NSC Number: 59256
• UNII: 94IEA0NV89
• DSSTox Substance ID: DTXSID9021267
• Nikkaji Number: J1.589J
• Wikipedia: Sesamol
• Wikidata: Q418080
• Metabolomics Workbench ID: 46218
• ChEMBL ID: CHEMBL1517998
• Mol file: 533-31-3.mol

Synonyms:3,4-methylenedioxyphenol;5-hydroxy-1,3-benzodioxole;sesamol;sesamol lithium;sesamol sodium;sesamol titanium (+4);sesamol, ion (1+)

Chemical Property of Sesamol

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 62-65 °C(lit.)
• Refractive Index: 1.4850 (estimate)
• Boiling Point: 274 °C at 760 mmHg
• PKA: 10.08±0.20(Predicted)
• Flash Point: 119.5 °C
• PSA: 38.69000
• Density: 1.394 g/cm³
• LogP: 1.12090
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: slightly soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

Sesamol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)O
• Description: Sesamol is found in sesame seeds and sesame oil. It is a well-known antioxidant. It has antioxidant, chemoprevention, antimutagenic, and antihepatotoxic activities and can induce the apoptosis of cancer and cardiovascular cells. It can be used in the synthesis of paroxetine.
• Uses: Sesamol is a natural component of sesame oil with antioxidant activity. Sesamol has potential protective effects against free radicals as well as some antifungal activity. Sesamol can also be used as an intermediate in the preparation of antidepressants such as Paroxetine (P205750). Sesamol (Paroxetine Anhydrous EP Impurity B) is a natural component of sesame oil with antioxidant activity. Sesamol has potential protective effects against free radicals as well as some antifungal activity. Sesamol can also be used as an intermediate in the preparation of antidepressants such as Paroxetine (P205750).

Technology Process of Sesamol

There total 47 articles about Sesamol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5-iodo-1,3-benzodioxole (5876-51-7) → Sesamol (533-31-3)

Guidance literature:

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;

DOI:10.1021/jacs.6b08114

Reference yield: 99.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → Sesamol (533-31-3)

Guidance literature:

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;

DOI:10.1021/jacs.6b08114

Reference yield: 95.0%

acetic acid benzo[1,3]dioxol-5-yl ester (326-58-9) → Sesamol (533-31-3)

Guidance literature:

With water; potassium hydroxide; In methanol; at 50 ℃; for 2h;

DOI:10.1248/cpb.58.242

upstream raw materials:

piperonal

3,4-methylenedioxypropiophenone

benzo[1,3]dioxolo-5-ylamine

3,4-methylenedioxyphenyl formate

Downstream raw materials:

5-(furan-2-carbonyloxy)-benzo[1,3]dioxole

sesamyl n-pentylether

sesamyl β-methallylether

sesamyl n-propylether

Refernces

• 1、 Chu, I-Hsuan,Hung, Wei-Ching,Lee, Wei-Ju,Su, Nan-Wei,Tsai, Hsin-Ya. "Formation of Samin Diastereomers by Acid-Catalyzed Transformation of Sesamolin with Hydrogen Peroxide". . p. 6430 - 6438. Retrieved 2020.
• 2、 -. "Synthesis process 3,4 -methylenedioxy phenol". . . Retrieved 2021/10/30.
• 3、 -. "Preparation method of sesamol". Paragraph 0022; 0026; 0032-0035. . Retrieved 2021/11/21.