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SMB00701

Sigma-Aldrich

Sesamolin

≥97%, from Sesamum indicum (sesame)

Sinónimos:

5-[(1S,3aR,4R,6aR)-4-(1,3-Benzodioxol-5-yloxy)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole

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About This Item

Fórmula empírica (notación de Hill):
C20H18O7
Número de CAS:
526-07-8
Peso molecular:
370.35
Código UNSPSC:
12352205
NACRES:
NA.25

origen biológico

Sesamum indicum (sesame)

Nivel de calidad

200

Ensayo

≥97%

Formulario

powder

solubilidad

DMSO: 10 mg/mL

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

ZZMNWJVJUKMZJY-AFHBHXEDSA-N

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Descripción general

Sesamolin is a furofuran lignan extracted from Sesamum indicum L. (sesame) seeds. Its solubility is very less in water. The chemical structure of sesamolin comprises two phenylpropanoids with their propyl side attached to a central carbon. It is reported in many other Sesamum species.

Acciones bioquímicas o fisiológicas

It also exerts antimicrobial, anti-melanogenesis, and neuroprotective effects.
Sesamolin 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.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H317

Consejos de prudencia

P280 - P302 + P352

Clasificaciones de peligro

Skin Sens. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000416829
0000416829
0000355405
0000355405
0000216689

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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
β-secretase inhibitors from sesame seeds and turmeric rhizomes
Murata K, et al.
Planta Medica, 82, S1-S381 (2016)
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.
Reny Rosalina et al.
Molecules (Basel, Switzerland), 26(19) (2021-10-14)
Sesame seeds are rich in lignan content and have been well-known for their health benefits. Unlike the other sesame lignan compounds (i.e., sesamin and sesamol), the study of the pharmacological activity of sesamolin has not been explored widely. This review
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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