All Photos(1)
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
Non-competitive Δ5-desaturase inhibitor.
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.
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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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.
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)
Differential and directional estrogenic signaling pathways induced by enterolignans and their precursors
Zhu Y, et al.
Testing, 12(2), e0171390-e0171390 (2017)
Zhong-Ping Ma et al.
Medical science monitor : international medical journal of experimental and clinical research, 25, 5312-5320 (2019-07-18)
BACKGROUND Osteoporosis is a common osteopathy, resulting in fractures, especially in elder people. Sesamin has many pharmacological effects, including supplying calcium. However, how sesamin might prevent osteoporosis is still under study. MATERIAL AND METHODS Bone marrow stromal cells (BMSCs) extracted
Jean Fotie et al.
Journal of natural products, 70(10), 1650-1653 (2007-09-21)
Three benzo[ c]phenanthridine alkaloids have been isolated from the stem bark of Garcinia lucida: dihydrochelerythrine ( 1), 6-acetonyldihydrochelerythrine ( 2), and its new derivative, ( S)1''-(9,10-dihydro-2',3'-dihydroxy-7,8-dimethoxy-10-methyl-1,2-benzophenanthridin-9-yl)propan-2''-one (lucidamine A) ( 3). The new diisoprenylated derivative of lucidamine B ( 4) was
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