Sesamin
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Sesamin
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CAS No:
607-80-7
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Formula:
C20H18O6
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Chemical Name:
Sesamin
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Synonyms:
1,3-Benzodioxole,5,5′-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-,(1S,3aR,4S,6aR)-;1,3-Benzodioxole,5,5′-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-,[1S-(1α,3aα,4α,6aα)]-;1H,3H-Furo[3,4-c]furan,tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-,(1S,3aR,4S,6aR)-;1H,3H-Furo[3,4-c]furan,1,3-benzodioxole deriv.;(1S,3aR,4S,6aR)-5,5′-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[1,3-benzodioxole];Sesamin;Fagarol;Sesamin,(+)-;(+)-Sesamin;d-Sesamin;Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan;Sezamin;NSC 36403;Zengxiaomin;δ-Sesamin;Sesavita;10590-92-8
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CAS No:
Description
Sesamin, abundant lignan found in sesame oil, is a potent and selective delta 5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis. Sesamin exerts effective neuroprotection against cerbral ischemia[1][2].
Solid
(+)-sesamin is a lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity. It has a role as an antineoplastic agent, a neuroprotective agent and a plant metabolite. It is a lignan, a member of benzodioxoles and a furofuran.
Characteristics
55.4
3.21920
crystalline
1.4±0.1 g/cm3
124 °C
504.4°C at 760 mmHg
212.3±30.0 °C
1.623
6.555 mg/L @ 25 °C (est)
−20°C
Drug Information
Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
asarinin
Sesamin Use and Manufacturing
A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expression of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level.
Computed Properties
Molecular Weight:354.4
XLogP3:2.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:354.11033829
Monoisotopic Mass:354.11033829
Topological Polar Surface Area:55.4
Heavy Atom Count:26
Complexity:482
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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