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1-Hydroxy-2,3,5-trimethoxyxanthone

$905

  • Brand : BIOFRON

  • Catalogue Number : AV-C10407

  • Specification : 98%

  • CAS number : 22804-49-5

  • Formula : C16H14O6

  • Molecular Weight : 302.27

  • PUBCHEM ID : 5318372

  • Volume : 5mg

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Catalogue Number

AV-C10407

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

302.27

Appearance

Yellow powder

Botanical Source

Structure Type

Xanthones

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC=CC2=C1OC3=CC(=C(C(=C3C2=O)O)OC)OC

Synonyms

1-Hydroxy-2,3,5-trimethoxy xanthone/1-hydroxyl-2,3,5-trimethoxyxanthone/1-Hydroxy-2,3,5-trimethoxyxanthone/Tovopyrifolin-C-3,5-di-O-methylether/9H-Xanthen-9-one,1-hydroxy-2,3,5-trimethoxy/1-Hydroxy-2,3,5-trimethoxy-9H-xanthen-9-one/1-Hydroxy-2,3,5-trimethoxyxanthon/1-hydroxy-2,3,5-trimethoxy-xanthen-9-one/9H-Xanthen-9-one, 1-hydroxy-2,3,5-trimethoxy-

IUPAC Name

1-hydroxy-2,3,5-trimethoxyxanthen-9-one

Applications

Density

1.3±0.1 g/cm3

Solubility

Flash Point

193.6±23.6 °C

Boiling Point

513.5±50.0 °C at 760 mmHg

Melting Point

184-186℃

InChl

InChI=1S/C16H14O6/c1-19-9-6-4-5-8-13(17)12-10(22-15(8)9)7-11(20-2)16(21-3)14(12)18/h4-7,18H,1-3H3

InChl Key

FFVKXGZKJBHJMS-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:22804-49-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

17822718

Abstract

1-Hydroxy-2, 3, 5-trimethoxyxanthone (HM-1) is a xanthone isolated from Halenia elliptica, a Tibetan medicinal herb. HM-1 (0.33-42.1 microM) produced a concentration-dependent relaxation in rat coronary artery rings pre-contracted with 1 microM 5-hydroxytryptamine (5-HT), with an EC(50) of 1.67+/-0.27 microM. Removal of the endothelium significantly affected the vasodilator potency of HM-1, resulting in 46% decrease in E(max) value. The endothelium-dependent effects of HM-1 was confirmed when its vasorelaxant effect was inhibited after addition of nitric oxide synthase (NOS) inhibitor N(omega)-nitro-l-arginine methyl ester (100 microM) or the soluble guanylate cyclase inhibitor 1H-[1, 2, 4] oxadiazolo [4,3-alpha] quinoxalin-1-one (ODQ, 10 microM). Atropine (100 nM), flurbiprofen (10 microM), propranolol (100 microM), pyrilamine (10 microM), cimetidine (10 microM) and SQ22536 (100 microM) had no effect on the vasorelaxant activity of HM-1 indicated the non-involvement of other receptor/enzyme systems. In endothelium-denuded coronary artery rings, the vasorelaxant effect of HM-1 was unaffected by potassium channel blockers such as tetraethylammonium (10 mM), iberiotoxin (100 nM), barium chloride (100 microM) and 4-aminopyridine (1 mM). The involvement of Ca(2+) channel in 5-HT-primed artery ring preparations incubated with Ca(2+)-free buffer was confirmed when HM-1 (9.93 microM) partially abolished the CaCl(2)-induced vasoconstriction (87% inhibition in intact-endothelium artery rings; 50% inhibition in endothelium-denuded rings). In the KCl-primed preparations incubated with Ca(2+)-free buffer, HM-1 (9.93 microM) produced a 27.3% inhibition in endothelium-denuded rings. HM-1 (3.31-33.1 microM) had minimal relaxant effects (14.4%-20.3%) on the contractile response generated by 10 microM phorbol 12,13-diacetate (PDA) in Ca(2+)-free solutions, suggesting minimal effects on intracellular Ca(2+) mechanisms. These findings suggest the vasodilator action of HM-1 involved both an endothelium-dependent mechanism involving NO and an endothelium-independent mechanism by inhibiting Ca(2+) influx through L-type voltage-operated Ca(2+) channels; a minor contribution to the effects of HM-1 may be related to inhibition of the protein kinase C-mediated release of intracellular Ca(2+) stores.

Title

Mechanisms of the vasorelaxant effect of 1-hydroxy-2, 3, 5-trimethoxy-xanthone, isolated from a Tibetan herb, Halenia elliptica, on rat coronary artery.

Author

Wang Y1, Shi JG, Wang MZ, Che CT, Yeung JH.

Publish date

2007 Sep 1

PMID

12939033

Abstract

Polygala paniculata L. yielded the xanthones 1-hydroxy-5-methoxy-2,3-methylenedioxyxanthone (1) and 1,5-dihydroxy-2,3-dimethoxyxanthone (2), together with coumarin murragatin and flavonol rutin. Their structures were established by chemical and spectroscopic methods (EIMS, IR, 1H and 13C NMR, NOE difference spectroscopy). By posterior analysis of an apolar crude extract using high resolution gas chromatography coupled to mass spectrometry (HRGC-MS) it was possible to characterize two sterol (spinasterol and delta25-spinasterol) and the minor 1-hydroxy-2,3,5-trimethoxyxanthone (3). Thus, the xanthone 3 was confirmed through of co-injection HRGC-MS of the respective extract with a certified standard obtained by methylation of 2 with diazomethane.

Title

Two xanthones from Polygala paniculata and confirmation of the 1-hydroxy-2,3,5-trimethoxy-xanthone at trace level by HRGC-MS

Author

Cristiano R1, Pizzolatti MG, Delle Monache F, Rezende CM, Branco A

Publish date

2003 Jul-Aug