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Merck
CN

S9314

Sesamin

≥95%, crystalline

Synonym(s):

Fagarol

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About This Item

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

Key Documents

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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.

wgk

WGK 3

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLBX2277
SLBW8178
SLBR7338V
SLBR3554V
SLBR4695V

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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)
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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