| Identification | Back Directory | [Name]
Sesamin | [CAS]
607-80-7 | [Synonyms]
SESAMIN
FAGAROL
SezaMin
Fsesamin
L-Sesamin
NSC 36403
d-Sesamin
SesameP.E.
SESAMIN(P)
SESAMIN(RG)
Sesamine70%
(+)-SESAMIN
Pseudocubebin
SesaMin(Fagarol)
SesaMin, froM SesaMuM indicuM
Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan
(1S,3aR,4S,6aR)-5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole
(1S,3aR,4S,6aR)-Tetrahydro-1,4-bis[3,4-(Methylenedioxy)phenyl]-1H,3H-Furo[3,4-c]furan
1,3-Benzodioxole,5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, (1S,3aR,4S,6aR)-
[1S-(1α,3aα,4α,6aα)]-5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole
(+)-5,5'-[(1S,3aβ,4S,6aβ)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]-bis-1,3-benzodioxole
(+)-5,5'-[(1S,3aβ,4β,6aβ)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(1,3-benzodioxole)
1,3-Benzodioxole,5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-,[1S-(1α,3aα,4α, 6aα)]-
1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, [1S-(1a,3aa,4a,6aa)]-
[1S-(1BETA,3ALPHA-BETA,4BETA,6ALPHA-BETA)]-5,5'-(TETRAHYDRO-1H,3H-FURO[3,4-C]FURAN-1,4-DIYL)BIS-1,3-BENZODIOXOLE | [Molecular Formula]
C20H18O6 | [MDL Number]
MFCD00216134 | [MOL File]
607-80-7.mol | [Molecular Weight]
354.35 |
| Chemical Properties | Back Directory | [Melting point ]
121.0 to 125.0 °C | [Boiling point ]
504.4±50.0 °C(Predicted) | [density ]
1.385±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO (>25 mg/ml) | [form ]
crystalline
| [color ]
White | [biological source]
Sesamum indicum (sesame) | [Merck ]
14,8470 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChIKey]
PEYUIKBAABKQKQ-AFHBHXEDSA-N | [LogP]
4.064 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Usage]
A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expr
ession of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level. | [Description]
Sesamin (607-80-7) is a natural product derived from sesame seeds with anticancer1, antioxidant2, anti-inflammatory/immunomodulatory3, and antidiabetic4,5 effects. It also displayed effects on cholesterol and fatty acid metabolism.6? Sesamin was recently found to inhibit bacterial L-tryptophan indole lyase (Ki = 7 μM).7 This enzyme reacts with dietary tryptophan to produce the uremic toxin indoxyl sulfate which exacerbates chronic kidney disease. | [Uses]
A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expr
ession of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level. | [Definition]
ChEBI: A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR | [General Description]
Sesamin is a fat-soluble furfuran lignan present in Sesamum indicum?L seeds. | [Biochem/physiol Actions]
Non-competitive Δ5-desaturase inhibitor. | [References]
Majdalawieh et al. (2017) A comprehensive review on the anti-cancer properties and mechanisms of action of sesamin, a lignan in sesame seeds (Sesamum indicum); Eur.? J. Pharmacol.?815 512
Kiso (2004) Antioxidative role of sesamin, a functional lignan in sesame seed, and its effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study; Biofactors 21 191
Majdalawieh et al. (2021) Immunomodulatory and anti-inflammatory effects of sesamin: mechanisms of action and future directions; Crit.? Rev. Food Sci. Nutr.?5 1
Shahi et al. (2017) Effect of Sesamin Supplementation on Glycemic Status, Inflammatory Markers, and Adiponectin Levels in Patients with Type 2 Diabetes Mellitus; J. Diet. Suppl.?14 65
Farbood et al. (2019) Sesamin: A promising protective agent against diabetes-associated cognitive decline in rats; Life Sci. 230 169
Majdalawieh et al. (2020) Effects of sesamin on fatty acid and cholesterol metabolism, macrophage cholesterol homeostasis and serum lipid profile: a comprehensive review; Eur. J. Pharmacol. 173417
Oikawa et al. (2022) (+)-Sesamin, a sesame lignan, is a potent inhibitor of gut bacterial tryptophan indole-lyase that is a key enzyme in chronic kidney disease pathogenesis; Biochem. Biophys. Res. Commun.?590 158 |
|
|