SMB00701

Sigma-Aldrich

Sesamolin

≥97%, from Sesamum indicum (sesame)

Synonym(s):
5-[(1S,3aR,4R,6aR)-4-(1,3-Benzodioxol-5-yloxy)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole
Empirical Formula (Hill Notation):
C20H18O7
CAS Number:
Molecular Weight:
370.35

Quality Level

biological source

Sesamum indicum (sesame)

assay

≥97%

form

powder

solubility

DMSO: 10 mg/mL

storage temp.

−20°C

SMILES string

[H][C@@]12[C@@H](C(C=C3)=CC4=C3OCO4)OC[C@]1([H])[C@@H](OC5=CC6=C(C=C5)OCO6)OC2

InChI

1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

InChI key

ZZMNWJVJUKMZJY-AFHBHXEDSA-N

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Biochem/physiol Actions

Sesamolin is a furofuran lignan extracted from sesame seeds. It is reported to have beneficial physiological properties such as antioxidant, anti-mutagenic, anti-aging and anti-inflammatory activities. It was also found to inhibit lipid peroxidation in rat liver and kidney.

Sesamolin enhances NK cell lysis activity by increasing the expression of NKG2D ligands on Burkitt′s lymphoma cells, presenting a potential immunotherapeutic value for cancer treatment. In addition, it was demonstrated that sesamolin inhibits β-secretase, presenting an important role for prevention of dementia by daily consumption.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

Skin Sens. 1

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Jeong Hwa Kim et al.
International immunopharmacology, 28(2), 977-984 (2015-08-25)
Sesamolin and sesamin are representative lignans found in sesame seed. The present study was designed to demonstrate the anti-cancer activity of sesamolin achieved by increasing the expression level of NKG2D ligands on Raji cells, which are derived from Burkitt's lymphoma....
β-secretase inhibitors from sesame seeds and turmeric rhizomes
Murata K, et al.
Planta Medica, 82, S1-S381 (2016)
Afaf Kamal-Eldin et al.
Recent patents on food, nutrition & agriculture, 3(1), 17-29 (2010-12-01)
Sesame seed contains very high levels (up to 2.5%) of furofuran lignans with beneficial physiological activities, mainly sesamin, sesamolin, and sesaminol glucosides. Reported activities of sesame seed lignans include inter alias modulation of fatty acid metabolism, inhibition of cholesterol absorption...
M H Kang et al.
The Journal of nutrition, 128(6), 1018-1022 (1998-06-18)
Although the sesame lignans, sesaminol and sesamolinol, have been shown to possess antioxidative activity, less is known about the metabolism and antioxidative properties of sesamolin, a major constituent of sesame oil. To determine the ability of sesamolin to act as...

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