Sesaminol
Basic information
- CAS
74061-79-3- Standard SMILES
Oc1cc2c(cc1[C@H]1OC[C@H]3[C@@H]1CO[C@@H]3c1ccc3c(c1)OCO3)OCO2- InChIKey
KQRXQIPRDKVZPW-ISZNXKAUSA-N- Molecular formula
- C20H18O7
- Average molar mass
- 370.4 g/mol
- Monoisotopic mass
- 370.10525291
Overview
Sesaminol is a furofuran that is cis-tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 6-hydroxy-1,3-benzodioxol-5-yl group at position 1S and a 1,3-benzodioxol-5-yl group at position 4S. It is metabolite found in sesame seeds. It has a role as an antioxidant and a plant metabolite. It is an organic hydroxy compound, a member of benzodioxoles and a furofuran.
Names & identifiers
- Preferred name
- Sesaminol
- IUPAC
- 6-[(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-benzodioxol-5-ol
- English name
- sesaminol
- Molecular formula
- C20H18O7
- Molecular weight
- 370.35
Names & synonyms
Sesaminol74061-79-36-[(1s,3ar,4s,6ar)-4-(1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-1,3-benzodioxol-5-olCHEBI:145778(1S-(1alpha,3aalpha,4alpha,6aalpha))-6-(4-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-1,3-benzodioxol-5-ol6-[(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-benzodioxol-5-ol6-((1S,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-1,3-benzodioxol-5-ol6-((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-benzodioxol-5-olRefChem:182568(+)-sesaminolJustisolinSesaminol, (+)-
Show more names
(1S,3aβ,6aβ)-1β-(6-Hydroxy-1,3-benzodioxol-5-yl)-4β-(1,3-benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan6-[(1S,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-1-yl]-1,3-benzodioxol-5-ol
QTS6XJP5LCorb2814216SCHEMBL12600772DTXSID50995513T2035111,3-Benzodioxol-5-ol, 6-(4-(1,3-benzodioxol-5-yl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-, (1S-(1alpha,3aalpha,4alpha,6aalpha))-1,3-Benzodioxol-5-ol, 6-[(1S,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-6-((1S,3aR,4S,6aR)-4-(Benzo[d][1,3]dioxol-5-yl)hexahydrofuro[3,4-c]furan-1-yl)benzo[d][1,3]dioxol-5-ol
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 75.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 558
Physicochemical properties
- Boiling point
- 504.7 · 504.7±50.0 °C(Predicted)
- Density
- 1.456 · 1.456±0.06 g/cm3(Predicted)
- pka
- 9.69 · 9.69±0.20(Predicted)
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - MISCELLANEOUS
Chemistry & industry
Applications
UsesSesaminol is an orally active activator for Nrf2-ARE pathway, that promotes the the nuclear translocation of Nrf2 and enhances the NQO1 expression, thereby enhances the cell's defense against oxidative stress. Sesaminol inhibits 6-OHDA (HY-B1081)-induced ROS production and apoptosis in cell SH-SY5Y. Sesaminol exhibits neuroprotective efficacy against Rotenone (HY-B1756)-induced Parkinson's disease[1].
Additional notes
DefinitionChEBI: Sesaminol is a furofuran that is cis-tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 6-hydroxy-1,3-benzodioxol-5-yl group at position 1S and a 1,3-benzodioxol-5-yl group at position 4S. It is metabolite found in sesame seeds. It has a role as a plant metabolite and an antioxidant. It is a member of benzodioxoles, a furofuran and an organic hydroxy compound.
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