Sesamin Chemical Properties

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.

InChI

InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2

InChIKey

PEYUIKBAABKQKQ-AFHBHXEDSA-N

SMILES

O1CC2C(C3=CC=C4OCOC4=C3)OCC2C1C1=CC=C2OCOC2=C1

LogP

4.064 (est)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29329990

MSDS

• Language:English Provider:Sesamin
• Language:English Provider:SigmaAldrich

Sesamin Usage And Synthesis

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.

Chemical Properties

White powder

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.

Uses

Sesamin has been used:

• as a lignan to study its effects on the osteoblastic differentiation of rat bone marrow stromal cells (BMSCs)
• as a standard for the isolation of sesamin from sesame oil
• as an enterolignan to study its effects on the proliferation of estrogen-receptor (ER)-positive human breast cancer MCF-7 cells

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

[1] AMIN F. MAJDALAWIEH  Gheyath K N  Mariam Massri. A comprehensive review on the anti-cancer properties and mechanisms of action of sesamin, a lignan in sesame seeds (Sesamum indicum)[J]. European journal of pharmacology, 2017, 815: Pages 512-521. DOI:10.1016/j.ejphar.2017.10.020
[2] KISO Y. Antioxidative roles of sesamin, a functional lignan in sesame seed, and it’s effect on lipid- and alcohol-metabolism in the liver: A DNA microarray study[J]. BioFactors, 2008, 21 1-4: 191-196. DOI:10.1002/biof.552210139
[3] AMIN F MAJDALAWIEH. Immunomodulatory and anti-inflammatory effects of sesamin: mechanisms of action and future directions.[J]. Critical reviews in food science and nutrition, 2022, 62 18: 5081-5112. DOI:10.1080/10408398.2021.1881438
[4] MAJID MOHAMMAD SHAHI. Effect of Sesamin Supplementation on Glycemic Status, Inflammatory Markers, and Adiponectin Levels in Patients with Type 2 Diabetes Mellitus.[J]. Journal of Dietary Supplements, 2017, 14 1: 65-75. DOI:10.1080/19390211.2016.1204404
[5] YAGHOOB FARBOOD . Sesamin: A promising protective agent against diabetes-associated cognitive decline in rats[J]. Life sciences, 2019, 230: Pages 169-177. DOI:10.1016/j.lfs.2019.05.071
[6] AMIN F. MAJDALAWIEH  Sarah M Y  Sarah Dalibalta. Effects of sesamin on fatty acid and cholesterol metabolism, macrophage cholesterol homeostasis and serum lipid profile: A comprehensive review[J]. European journal of pharmacology, 2020, 885: Article 173417. DOI:10.1016/j.ejphar.2020.173417
[7] DAIKI OIKAWA . (+)-Sesamin, a sesame lignan, is a potent inhibitor of gut bacterial tryptophan indole-lyase that is a key enzyme in chronic kidney disease pathogenesis[J]. Biochemical and biophysical research communications, 2022, 590: Pages 158-162. DOI:10.1016/j.bbrc.2021.12.088

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