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SML1766

Sigma-Aldrich

Diphyllin

≥98% (HPLC)

Synonym(s):

9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-naphtho[2,3-c]furan-1(3H)-one, NSC 309691

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About This Item

Empirical Formula (Hill Notation):
C21H16O7
CAS Number:
22055-22-7
Molecular Weight:
380.35
MDL number:
MFCD00808222
UNSPSC Code:
12352200
PubChem Substance ID:
329826058
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

OC1=C2C(C(OC2)=O)=C(C3=CC=C(OCO4)C4=C3)C5=CC(OC)=C(OC)C=C51

InChI

1S/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

InChI key

VMEJANRODATDOF-UHFFFAOYSA-N

General description

Diphyllin, a major glycoside compound, is a plant-derived lignan. It is present in Cleistanthus collinus.

Application

Diphyllin has been used to study its antibacterial and antibiofilm activities against fish pathogens.

Biochem/physiol Actions

Diphyllin has shown potential to be used in a novel treatment for bone problems characterized by excessive resorption.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mette G Sørensen et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 22(10), 1640-1648 (2007-06-20)
Dissolution of the inorganic phase of bone by the osteoclasts mediated by V-ATPase and ClC-7 is a prerequisite for bone resorption. Inhibitors of osteoclastic V-ATPase or ClC-7 are novel approaches for inhibition of osteoclastic bone resorption. By testing natural compounds
Zhitao Zhang et al.
European journal of medicinal chemistry, 82, 466-471 (2014-06-16)
The concise syntheses of two natural diphyllin glycosides Cleistanthin-A (CA), Cleistanthoside-A (CleA) and its derivative, Cleistanthoside-A tetraacetate (CleT), have been achieved. They were evaluated for their in vitro anti-proliferative activities against MCF-7, HeLa, HepG2, HCT-116, U251 cancer cell lines by
Yapeng Lu et al.
European journal of pharmacology, 771, 130-138 (2015-12-23)
The vacuolar H(+)-ATPase (V-ATPase) has recently been proposed as a key target for new strategies in cancer treatment. Our previous work has proved that diphyllin glycoside is a novel inhibitor of V-ATPase. Here the cytotoxic effects of ZT-25, the most

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