Sesamin

Sesamin
Compound Structure:
Synonyms: sesamin; 607-80-7; Fagarol ;Sezamin; (+)-Sesamin
Compound ID: NMPC-1478
PubChem ID:

72307

Molecular Formula: C20H18O6
Canonical SMILES: C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
InChIKey: PEYUIKBAABKQKQ-AFHBHXEDSA-N
About the compound:

(+)-Sesamin is a lignan, specifically the 1S,3aR,4S,6aR stereoisomer of tetrahydro-1H,3H-furo[3,4-c]furan, which is substituted with 1,3-benzodioxole groups at positions 1 and 4. It has been isolated from Cinnamomumcamphora and is known for its cytotoxic activity, making it of interest as an antineoplastic (anti-cancer) agent. Additionally, (+)-sesamin functions as a neuroprotective agent and is recognized as a plant metabolite. Sesamin is also found in the bark of Fagara plants and is a component of sesame oil, although it is a minor constituent. It has been utilized as a dietary supplement for fat reduction. After ingestion, sesamin is metabolized into enterolactone, which has a relatively short elimination half-life of less than 6 hours. This rapid metabolism and excretion may influence the duration and intensity of its biological effects. In sesame oil, sesamin, along with sesamolin, constitutes a small fraction of the total oil content, averaging only about 0.14% by mass. Despite this low concentration, the presence of sesamin contributes to the nutritional and potential health benefits of sesame oil. Given its roles and pharmacological potential, sesamin continues to be an area of interest in research, particularly in exploring its applications in cancer therapy and neuroprotection. The ongoing study of sesamin and similar plant-derived compounds helps in understanding their potential therapeutic benefits and mechanisms of action.

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

354.4 g/mol

XLogP3-AA

2.7

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

6

Rotatable Bond Count

2

Exact Mass

354.11033829 g/mol

Monoisotopic Mass

354.11033829 g/mol

Topological Polar Surface Area

55.4Ų

Heavy Atom Count

26

Formal Charge

0

Complexity

482

Isotope Atom Count

0

Defined Atom Stereocenter Count

4

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Melting Point

123 - 124 °C

Source: PubChem       

Source Species: Musa sapientum
Musa acuminata
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