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About This Item
Empirical Formula (Hill Notation):
C20H18O6
CAS Number:
Molecular Weight:
354.35
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
Sesamum indicum (sesame)
Assay
≥95%
form
crystalline
shipped in
wet ice
storage temp.
−20°C
SMILES string
C1Oc2ccc(cc2O1)[C@H]3OC[C@H]4[C@@H]3CO[C@@H]4c5ccc6OCOc6c5
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/t13-,14-,19+,20+/m0/s1
InChI key
PEYUIKBAABKQKQ-AFHBHXEDSA-N
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General description
Sesamin is a fat-soluble furfuran lignan present in Sesamum indicum L seeds.
Application
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
Biochem/physiol Actions
Sesamin can lower cholesterol effects in humans. It is involved in preventing high blood pressure and increases vitamin E levels. Sesamin exhibits anti-cancer, anti-proliferative, anti-metastatic and anti-inflammatory properties. It also exhibits pro-apoptotic and pro-autophagocytic properties. Sesamin has its effects on lipid and carbohydrate metabolism. It also has effects on hypertension and free radical scavenging.
Non-competitive Δ5-desaturase inhibitor.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Sens. 1
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Sesamin promotes osteoblastic differentiation and protects rats from osteoporosis
Ma Z, et al.
Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 25(16), 5312-5312 (2019)
S Shimizu et al.
Lipids, 26(7), 512-516 (1991-07-01)
Incubation with sesame oil increases the mycelial dihomo-gamma-linolenic acid content of an arachidonic acid-producing fungus, Mortierella alpina, but decreases its arachidonic acid content [Shimizu, S., K. Akimoto, H. Kawashima, Y. Shinmen and H. Yamada (1989) J. Am. Oil Chem. Soc.
Differential and directional estrogenic signaling pathways induced by enterolignans and their precursors
Zhu Y, et al.
Testing, 12(2), e0171390-e0171390 (2017)
A comprehensive review on the anti-cancer properties and mechanisms of action of sesamin, a lignan in sesame seeds (Sesamum indicum)
Majdalawieh A F, et al.
European Journal of Pharmacology, 815, 512-521 (2017)
An updated method for isolation, purification and characterization of clinically important antioxidant lignans-Sesamin and sesamolin, from sesame oil
Dar A, et al.
Industrial Crops and Products, 64(16), 201-208 (2015)
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