Structure

Sinensetin

CAS
2306-27-6
Catalog Number
ACM2306276
Category
Inhibitors
Molecular Weight
372.37
Molecular Formula
C20H20O7

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Specification

Description
Sinensetin is a methylated flavone found in certain citrus fruits. pocess potent antiangiogenesis and anti-inflammatory, sinensetin enhances adipogenesis and lipolysis.In vitro: Sinensetin promots adipogenesis in 3T3-L1 preadipocytes growing in incomplete differentiation medium, sinensetin enhances adipogenesis and lipolysis by increasing cAMP levels. Sinensetin shows anti-inflammatory activity by regulating the protein level of inhibitor κB-α (IκB-α). In vivo: Sinensetin has the most potent antiangiogenesis activity and the lowest toxicity, inhibits angiogenesis by inducing cell cycle arrest in the G0/G1 phase in HUVEC culture and downregulating the mRNA expressions of angiogenesis genes flt1, kdrl, and hras in zebrafish.
IUPAC Name
2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one
Canonical SMILES
COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)OC)OC
InChI
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3
InChI Key
LKMNXYDUQXAUCZ-UHFFFAOYSA-N
Appearance
White-pale yellow powder
Storage
Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
Shipping
Can be shipped at room temperature, where not in use may vary.
Source
Plantsother families

Upstream Synthesis Route 1

  • 114021-62-4
  • 2306-27-6

Reference: [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang
[Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]
[2]Oliverio; Bargellini
[Gazzetta Chimica Italiana, 1948, vol. 78, p. 386,394]

Upstream Synthesis Route 2

  • 6962-57-8
  • 24824-54-2
  • 2306-27-6

Reference: [1]Murti; Seshadri
[Proceedings - Indian Academy of Sciences, Section A, 1948, # 27, p. 217,220]

Upstream Synthesis Route 3

  • 18003-33-3
  • 77-78-1
  • 2306-27-6

Reference: [1]Morita
[Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 66,67]
[2]Shaw, S. C.; Azad, R.; Mandal, S. P.; Gandhi, R. S.
[Journal of the Indian Chemical Society, 1988, vol. 65, p. 107 - 109]
[3]Hossain, M. Amzad; Ismail, Zhari
[Pakistan Journal of Scientific and Industrial Research, 2004, vol. 47, # 4, p. 268 - 271]

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