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S9314

Sigma-Aldrich

Sesamin

≥95%, crystalline

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Synonym(s):
Fagarol
Empirical Formula (Hill Notation):
C20H18O6
CAS Number:
607-80-7
Molecular Weight:
354.35
MDL number:
MFCD00216134
UNSPSC Code:
12352200
PubChem Substance ID:
24899834
NACRES:
NA.77

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
Amin F Majdalawieh et al.
European journal of pharmacology, 815, 512-521 (2017-10-17)
Sesamin is the major active ingredient is Sesamum indicum seeds. Several studies revealed that sesamin possesses potent anti-cancer properties. The anti-cancer effects of sesamin have been mainly attributed to its anti-proliferative, pro-apoptotic, anti-inflammatory, anti-metastatic, anti- and pro-angiogenic, and pro-autophagocytic activities.
N Hirose et al.
Journal of lipid research, 32(4), 629-638 (1991-04-01)
The effects of sesamin, a lignan from sesame oil, on various aspects of cholesterol metabolism were examined in rats maintained on various dietary regimens. When given at a dietary level of 0.5% for 4 weeks, sesamin reduced the concentration of
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