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SMB00701

Sigma-Aldrich

Sesamolin

≥97%, from Sesamum indicum (sesame)

Sinônimo(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

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About This Item

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

fonte biológica

Sesamum indicum (sesame)

Nível de qualidade

200

Ensaio

≥97%

Formulário

powder

solubilidade

DMSO: 10 mg/mL

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

ZZMNWJVJUKMZJY-AFHBHXEDSA-N

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Descrição geral

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.

Ações bioquímicas/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

Palavra indicadora

Warning

Frases de perigo

H317

Declarações de precaução

P280 - P302 + P352

Classificações de perigo

Skin Sens. 1

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
069M4031V
067M4193V
107M4133V
12170501
12170502

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Formiato de amônio reagent grade, 97%

Sigma-Aldrich

156264

Formiato de amônio

Ácido L-ascórbico British Pharmacopoeia (BP) Reference Standard

BP461

Ácido L-ascórbico

Ácido acético analytical standard

Supelco

71251

Ácido acético

1-propanol anhydrous, 99.7%

Sigma-Aldrich

279544

1-propanol

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
T Lind et al.
Acta orthopaedica Belgica, 58(1), 81-83 (1992-01-01)
The intra-articular pressures in the glenohumeral joint in different positions were measured in 12 cadaveric shoulders. The lowest pressure was found in abduction combined with traction. A significant rise in pressure was seen in positions combining flexion or abduction with
β-secretase inhibitors from sesame seeds and turmeric rhizomes
Murata K, et al.
Planta Medica, 82, S1-S381 (2016)
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