Basic information
- CAS
607-80-7- Standard SMILES
c1cc2c(cc1[C@H]1OC[C@H]3[C@@H]1CO[C@@H]3c1ccc3c(c1)OCO3)OCO2- InChIKey
PEYUIKBAABKQKQ-AFHBHXEDSA-N- Molecular formula
- C20H18O6
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.11033829
Overview
(+)-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.
Names & identifiers
- Preferred name
- Sesamin
- IUPAC
- 5-[(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
- English name
- Sesamin
- Molecular formula
- C20H18O6
- Molecular weight
- 354.35
Names & synonyms
sesamin607-80-7FagarolSezamin(+)-Sesamind-SesaminD-(+)-SesaminCHEBI:66470NSC-36403S7946O4P765-[(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxoleDTXSID301030528
Show more names
L-SesaminSesameP.E.FsesaminNSC 36403AI3-00811
1H,3H-Furo(3,4-c)furan, tetrahydro-1,4-bis(3,4-(methylenedioxy)phenyl)-, (1S,3aR,4S,6aR)-1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis-, (1S-(1alpha,3a alpha,4alpha,6a alpha))-epi-sesamin5-((3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-6-yl)-1,3-benzodioxoleRefChem:47774DTXCID701515609pseudocubebinEpisesamin
Database identifiers
- CAS
607-80-7、81602-22-4- PubChem CID
- 72307
- DTXSID
DTXSID301030528- ChEMBL
CHEMBL252915- ChEBI
CHEBI:66470
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 55.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 482
Experimental & physicochemical properties
Melting Point123 - 124 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 121 to · 121.0 to 125.0 °C
- Boiling point
- 504.4 · 504.4±50.0 °C(Predicted)
- Density
- 1.385 · 1.385±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (>25 mg/ml)
- form
- crystalline
- color
- White
- biological source
- Sesamum indicum (sesame)
- Merck
- 14 · 14,8470
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChI
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
H317 (33.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationChemical: 1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesSkin Sens. 1 (33.3%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29329990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P362+P364
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used to lower plasma CHOLESTEROL levels.
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.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Cellular LocationsCytoplasm
Applications
DescriptionSesamin (607-80-7) is a natural product derived from sesame seeds with anticancer1, antioxidant2, anti-inflammatory/immunomodulatory3, and antidiabetic4,5 effects. It also displayed effects on cholesterol and fatty acid metabolism.6 Sesamin was recently found to inhibit bacterial L-tryptophan indole lyase (Ki = 7 μM).7 This enzyme reacts with dietary tryptophan to produce the uremic toxin indoxyl sulfate which exacerbates chronic kidney disease.
UsesA 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 expr ession of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level.
UsesSesamin 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
General DescriptionSesamin is a fat-soluble furfuran lignan present in Sesamum indicumL seeds.
Suppliers
Related reactions
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Compound notes
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