epi-Sesamin Monocatechol

Base Information

• Chemical Name: epi-Sesamin Monocatechol
• CAS No.: 1105568-81-7
• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.348
• DSSTox Substance ID: DTXSID20693438
• ChEMBL ID: CHEMBL1688936
• Mol file: 1105568-81-7.mol

Synonyms:epi-Sesamin Monocatechol;1105568-81-7;4-[(3aR,6aR)-6-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]benzene-1,2-diol;CHEMBL1688936;DTXSID20693438;4-[(3aR,6aR)-4-(2H-1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]benzene-1,2-diol

Chemical Property of epi-Sesamin Monocatechol

Chemical Property:

• PSA: 77.38000
• LogP: 2.90170
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 342.11033829
• Heavy Atom Count: 25
• Complexity: 487

Purity/Quality:

98% ^*data from raw suppliers

epi-SesaminMonocatechol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC(=C(C=C5)O)O
• Isomeric SMILES: C1[C@H]2[C@H](COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC(=C(C=C5)O)O
• Uses: A Sesamin (S280500) metabolite which acts as antioxidant in the liver.

Technology Process of epi-Sesamin Monocatechol

There total 6 articles about epi-Sesamin Monocatechol 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: 71.0%

sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7) → (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane (1105568-81-7) + (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane (340167-81-9)

Guidance literature:

sesamin; With lead(IV) tetraacetate; In toluene; at 90 ℃; for 2h;

With water; In acetonitrile; at 70 ℃; for 3h;

DOI:10.1016/j.bioorg.2019.03.077

Reference yield:

episesamin (133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,133-03-9) → (7α,7'β,8α,8'α)-3,4-dihydroxy-3',4'-methylenedioxy-7,9':7',9-diepoxylignane (340167-83-1,1105568-81-7)

Guidance literature:

With ascorbate; sesamin; 2-hydroxyethanethiol; In tetrahydrofuran; dimethyl sulfoxide; at 28 ℃; pH=8;

DOI:10.1073/pnas.1605050113

Reference yield:

(-)-asarinin (133-03-9,133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9) → C19H18O6 (1105568-81-7) + C18H18O6 (340167-81-9)

Guidance literature:

With ascorbate; sesamin; 2-hydroxyethanethiol; In tetrahydrofuran; dimethyl sulfoxide; at 28 ℃; pH=8;

DOI:10.1073/pnas.1605050113

upstream raw materials:

sesamin

demethylpiperitol 4-O-β-D-glucopyranoside

episesamin

(-)-asarinin

Refernces

• 1、 Tian, Li-Wen,Yang, Chong-Ren,Zhang, Ying-Jun. "Phenolic compounds from the fresh leaves of eucalyptus maideni". . p. 2194 - 2202. Retrieved 2010.
• 2、 Kumano, Takuto,Fujiki, Etsuko,Hashimoto, Yoshiteru,Kobayashi, Michihiko. "Discovery of a sesamin-metabolizing microorganism and a new enzyme". . p. 9087 - 9092. Retrieved 2016/08/12.