Xanthone

Category	Influenza Virus
CAS	90-47-1
Description	Xanthonoid Purified from Hypericum perforatum.

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Product Information

Synonyms	9H-Xanthen-9-one; Benzophenone oxide; Benzophenone oxide
IUPAC Name	xanthen-9-one
Molecular Weight	196.201
Molecular Formula	C13H8O2
Canonical SMILES	C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3O2
InChI	InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
InChIKey	JNELGWHKGNBSMD-UHFFFAOYSA-N
Boiling Point	351.0 °C
Melting Point	172-174 °C
Flash Point	169.8±13.1 °C
Purity	> 98 % (GC)
Density	1.277 g/cm³
Solubility	Chloroform, not well in alcohol
Appearance	Off-white powder
Storage	Store at +4 °C, in dark place.
Complexity	237
Exact Mass	196.052429494
Index Of Refraction	1.643
In Vitro	Xanthone is a phenolic compound found in a few higher plant families; it has a variety of biological activities, including antioxidant, anti-inflammatory, and anticancer properties. Xanthone significantly suppressed the phosphorylation of mitogen-activated protein kinases (MAPKs) and nuclear factor-kappa B (NF-κB) and activation of caspase-1 signaling pathway in vitro model. Xanthone could be loaded in these micelles up to 2 mg/mL with ~100% entrapment efficiency and ~20% loading capacity. The average particle diameter of the xanthone loaded mPEG-b-p(HPMAm-Lac(2)) micelles as determined by dynamic light scattering ranged from 84 to 112 nm. In vitro assays showed that xanthone in its free form as well as loaded in polymeric micelles had a high cytotoxicity towards both doxorubicin sensitive and, importantly, resistant cancer cells.
In Vivo	The treatment with xanthone reduced the production of pro-inflammatory cytokines and chemokines including interleukin (IL)-1β, IL-6, IL-8, and expression of chemokines thymus and activation-regulated chemokine (TARC) and macrophage-derived chemokine (MDC) in tumor necrosis factor (TNF)-α and interferon (IFN)-γ-stimulated HaCaT cells. Xanthone also suppressed the production of pro-inflammatory cytokines, chemokines, and allergic mediators in phorbol myristate acetate/A23187 calcium ionophore (PMACI)-stimulated HMC-1 cells. Additionally, xanthone administration alleviated 2,4-dinitrofluorobenzene (DNFB)-induced atopic dermatitis like-skin lesion by reducing the serum levels of immunoglobulin E (IgE), histamine, and pro-inflammatory cytokines and suppressing MAPKs phosphorylation. Xanthone administration also inhibited mortality due to compound 48/80-induced anaphylactic shock and suppressed the passive cutaneous anaphylaxis (PCA) reaction mediated by IgE.
PSA	30.21000
Target	Bacterial; Influenza Virus; Fungal; Apoptosis
Vapor Pressure	0.0±0.8 mmHg at 25°C
XLogP3-AA	3.4