Sesamolin - analytical standard, ≥98% , CAS No.526-07-8

CAS: 526-07-8 Cat. No.: S115692 Molecular Weight: 370.353 EC Number: 683-102-3 PubChem CID: 101746

GRADE & PURITY Analytical standard, ≥98%

Synonyms

DTXCID301323428 | AI3-20978 | Q-100595 | SESAMOLIN [MI] | A1-06842 | AC-35092 | Sesamolin | Q15720551 | 1,3-BENZODIOXOL-5-YL (1R,3AR,4S,6AR)-4-(1,3-BENZODIOXOL-5-YL)PERHYDROFURO(3,4-C)FURAN-1-YL ETHER | 5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

DTXCID301323428 | AI3-20978 | Q-100595 | SESAMOLIN [MI] | A1-06842 | AC-35092 | Sesamolin | Q15720551 | 1, 3-BENZODIOXOL-5-YL (1R, 3AR, 4S, 6AR)-4-(1, 3-BENZODIOXOL-5-YL)PERHYDROFURO(3, 4-C)FURAN-1-YL ETHER | 5-[[(3S, 3aR, 6R, 6aR)-3-(1, 3-benzodioxol-5-yl)-1, 3, 3a,

Specifications & Purity

analytical standard, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C2C(COC2OC3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
• IUPAC Name: 5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole
• InChIKey: ZZMNWJVJUKMZJY-AFHBHXEDSA-N
• INCHI: 1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
• Isomeric SMILES: C1[C@H]2[C@H](CO[C@@H]2OC3=CC4=C(C=C3)OCO4)[C@H](O1)C5=CC6=C(C=C5)OCO6
• PubChem CID: 101746
• Molecular Weight: 370.353

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzodioxoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzodioxoles
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzodioxoles
• Alternative Parents: Furofurans Benzenoids Tetrahydrofurans Oxacyclic compounds Dialkyl ethers Acetals Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzodioxole - Furofuran - Benzenoid - Tetrahydrofuran - Oxacycle - Ether - Dialkyl ether - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SI Tchem Sucrase-isomaltase (84 Activities)

Discover Target: SI

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Gaa Acidic alpha-glucosidase (551 Activities)

Discover Target: Gaa

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 370.400 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 370.105 Da
• Monoisotopic Mass: 370.105 Da
• Topological Polar Surface Area: 64.599 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 544.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jie Du, Xiaodong Chen, Yongshun Zhao, Tingting Zhao, Dalong Wang, Zujia Chen, Changyuan Wang, Qiang Meng, Jialin Yao, Huijun Sun, Kexin Liu, Jingjing Wu.  (2022)  Characterization of three naturally occurring lignans, sesamol, sesamolin, and sesamin, as potent inhibitors of human cytochrome P450 46A1: Implications for treating excitatory neurotoxicity..  Frontiers in Pharmacology,      [PMID:36483743] [10.3389/fphar.2022.1046814]

2. Liumin Huang, Jun Li, Yanlan Bi, Yanhui Xu, Yanmei Wang, Jian Wang, Dan Peng.  (2021)  Simultaneous determination of α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, sesamin, sesamolin, sesamol, and asarinin in sesame oil by normal-phase high performance liquid chromatography.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2021.104132]

3. Lipeng Han, Jiahui Li, Shujie Wang, Weiwei Cheng, Lukai Ma, Guoqin Liu, Dongxue Han, Li Niu.  (2020)  The inhibitory effects of sesamol and sesamolin on the glycidyl esters formation during deodorization of vegetables oils.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  101  (9): (3605-3612).  [PMID:33275282] [10.1002/jsfa.10989]

4. Zhenzhen Xia, Tian Yi, Yan Liu.  (2019)  Rapid and nondestructive determination of sesamin and sesamolin in Chinese sesames by near-infrared spectroscopy coupling with chemometric method.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:31727518] [10.1016/j.saa.2019.117777]

5. Yan Liu, Zhenzhen Xia, Liyun Yao, Yang Wu, Yan Li, Shan Zeng, Hao Li.  (2019)  Discriminating geographic origin of sesame oils and determining lignans by near-infrared spectroscopy combined with chemometric methods.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2019.103327]