22055-22-7

Basic information

• Product Name: diphyllin
• Synonyms: 4-Hydroxy-6,7-dimethoxy-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one;9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one;Diphyllin【naphthofuran】;NSC 309691
• CAS NO: 22055-22-7
• Molecular Formula: C₂₁H₁₆O₇
• Molecular Weight: 380.35
• Mol File: 22055-22-7.mol

Chemical Properties

• Melting Point: 290℃ (methanol )
• Boiling Point: 638.8°C at 760 mmHg
• Flash Point: 232.4°C
• Appearance: /
• Density: 1.445±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 6.53E-17mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: 2-8°C
• PKA: 7.82±0.20(Predicted)
• CAS DataBase Reference: diphyllin(CAS DataBase Reference)
• NIST Chemistry Reference: diphyllin(22055-22-7)
• EPA Substance Registry System: diphyllin(22055-22-7)

Safety Data

• Hazardous Substances Data: 22055-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Diphyllin is used as an active compound for its antibacterial and antibiofilm activities. It is particularly effective against fish pathogens, making it a valuable asset in the aquaculture industry for the prevention and treatment of bacterial infections in fish.
Used in Aquaculture Industry:
In the aquaculture sector, diphyllin is utilized as a natural alternative to conventional antibiotics. Its application aims to reduce the reliance on synthetic chemicals, which can lead to antibiotic resistance and environmental concerns. By leveraging the natural antibacterial properties of diphyllin, the industry can promote healthier and more sustainable fish farming practices.

Biochem/physiol Actions

Diphyllin is a natural arylnaphthalene that exhibits potent anticancer and antiviral activities. It is a potent inhibitor of vacuolar H(+)-ATPase (V-ATPase) that inhibits lysosomal acidification in osteoclasts.

InChI:InChI=1/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3

Upstream product

• 1356021-67-4 4-O-(D-apio-β-D-furanosyl-(1->6)-β-D-glucopyranosyl)diphyllin 
• 67-56-1 methanol 
• 81425-03-8 C₄₅H₅₈O₂₀ 
• 81417-77-8 cleistanthin E 

Downstream Products

• 17951-19-8 justicidin B 
• 25001-57-4 justicidin A 
• 30021-77-3 cleistanthin B 
• 1356825-38-1 4-O-(6-O-benzyl-β-D-galactopyranosyl)diphyllin 
• 1356825-37-0 4-O-(6-O-benzyl-β-D-glucopyranosyl)diphyllin 

Relevant articles and documents

A new arylnaphthalide lignan from justicia prostrata gamble

A new arylnaphthalide lignan glycosides, 4-O-β-D-apiofuranosyl- (1→6'')-β-D-glucopyranosyldiphyllin (1), together with three known compounds, procumphthalide-A, cilinaphthalide-A, justicidinoside-B, have been isolated from the whole plant of Justicia prostrata. The use of IR, UV, one and two-dimensional NMR spectroscopy and chemical methods were applied for the identification of these compounds.

New lignan glycosides with potent antiinflammatory effect, isolated from Justicia ciliata

Two new lignan glycosides, 4-O-[α-L-arabinopyranosyl-(1'''→2'')-β-D-xylopyranosyl-(1'''→5'')-β-D-ap iofuranosyl] diphyllin (1), named ciliatoside A (1), and 4-O-{[β-D-apiofuranosyl-(1''''→3''')-α-L-arabinopyranosyl-(1''''→2'')] [β-D-xylopyranosyl-(1''''→5'')]-β-D-apiofuranosyl}diphyllin (2), named ciliatoside B (2), were isolated from the whole plant of Justicia ciliata. The structures of 1 and 2 were determined by spectral and chemical methods. Compounds 1 and 2 strongly inhibited the accumulation of NO2- in lipopolysaccharide-stimulated RAW 264.7 cells in a concentration-dependent manner with IC50 values of 27.1 ± 1.6 and 29.4 ± 1.4 μM, respectively.

NEM LIGNANS FROM THE HEARTWOOD OF CLEISTANTHUS COLLINUS

The isolation and characterisation of five new compounds and nine known compounds from the heartwood of Cleistanthus collinus are reported.The new compounds are wodeshiol 16, 3,4-dihydrotaiwanin C 20, and three new glycosides 24, 25 and 26 of diphyllin and taiwanin E.The 1H and 13C NMR spectra of these compounds are also reported.