structure of Zedoarofuran

Zedoarofuran

CAS No.: 213833-34-2
M. Wt: 264.32
M. Fa: C15H20O4
InChI Key: QXEXMTIZXNCRJO-BSLXNSKLSA-N

Names and Identifiers of Zedoarofuran

CAS Number

213833-34-2

IUPAC Name

(4aS,5R,8S,8aS)-5,8-dihydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydro-4aH-benzo[f][1]benzofuran-4-one

InChI

InChI=1S/C15H20O4/c1-8-7-19-9-6-14(2)10(16)4-5-15(3,18)13(14)12(17)11(8)9/h7,10,13,16,18H,4-6H2,1-3H3/t10-,13-,14+,15+/m0/s1

InChIKey

QXEXMTIZXNCRJO-BSLXNSKLSA-N

Canonical SMILES

CC1=COC2=C1C(=O)C3C(CCC(C3(C2)C)O)(C)O

Isomeric SMILES

CC1=COC2=C1C(=O)[C@@H]3[C@](CC[C@@H]([C@]3(C2)C)O)(C)O

Physical and chemical properties of Zedoarofuran

Boiling Point

424.8±45.0 °C at 760 mmHg

Density

1.3±0.1 g/cm3

Exact Mass

264.136169

Flash Point

210.7±28.7 °C

Index of Refraction

1.570

LogP

2.35

Molecular Formula

C15H20O4

Molecular Weight

264.32

Vapour Pressure

0.0±1.1 mmHg at 25°C

Applications of Zedoarofuran

Zedoarofuran has several applications in various fields:

  • Pharmaceuticals: Due to its anticancer and antimicrobial properties, it is explored as a potential lead compound for drug development.
  • Cosmetics: Its anti-inflammatory effects make it a candidate for formulations aimed at skin health and anti-aging.
  • Food Industry: Zedoarofuran's antimicrobial properties could be utilized as a natural preservative in food products.

Interaction Studies of Zedoarofuran

Research on zedoarofuran's interactions with biological molecules has revealed:

  • Binding Affinity: Interaction studies indicate that zedoarofuran binds moderately to human serum albumin, which may influence its pharmacokinetics and bioavailability in the body.
  • Molecular Docking Studies: Computational studies have provided insights into how zedoarofuran interacts with various protein targets, suggesting mechanisms of action relevant to its therapeutic effects.

Biological Activity of Zedoarofuran

Zedoarofuran exhibits significant biological activities, including:

  • Anticancer Properties: Studies have shown that zedoarofuran possesses cytotoxic effects against various cancer cell lines, such as gastric cancer AGS cells, with IC50 values indicating effective inhibition of cell proliferation.
  • Antimicrobial Activity: The compound has demonstrated antibacterial properties against both Gram-positive and Gram-negative bacteria, suggesting its potential as a natural antimicrobial agent.
  • Anti-inflammatory Effects: Zedoarofuran may inhibit pro-inflammatory pathways, contributing to its therapeutic potential in managing inflammatory diseases.