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Gentisin

$768

  • Brand : BIOFRON

  • Catalogue Number : BD-D0629

  • Specification : HPLC≥98%

  • CAS number : 437-50-3

  • Formula : C14H10O5

  • Molecular Weight : 258.229

  • PUBCHEM ID : 5281636

  • Volume : 5mg

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Catalogue Number

BD-D0629

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

-20℃

Molecular Weight

258.229

Appearance

Powder

Botanical Source

Polygalae radix

Structure Type

Xanthones

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=C2C(=C1)OC3=C(C2=O)C=C(C=C3)O)O

Synonyms

GENTIANIC ACID/1,7-dihydroxy-3-methoxy-9H-xanthen-9-one/Gentisine/1,7-Dihydroxy-3-methoxy-xanthon/Gentisin/1,7-Dihydroxy-3-methoxy-xanthen-9-on/1,7-dihydroxy-3-methoxyxanthen-9-one/Xanthen-9-one,1,7-dihydroxy-3-methoxy/Gentianin/1,7-dihydroxy-3-methoxy-xanthen-9-one/1,7-Dihydroxy-3-methoxyxanthone

IUPAC Name

1,7-dihydroxy-3-methoxyxanthen-9-one

Applications

Gentisin is a natural compound isolated from Gentianae radix (Gentianaceae) with mutagenic activities[1].

Density

1.48g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

205.2ºC

Boiling Point

519.9ºC at 760mmHg

Melting Point

InChl

InChI=1S/C14H10O5/c1-18-8-5-10(16)13-12(6-8)19-11-3-2-7(15)4-9(11)14(13)17/h2-6,15-16H,1H3

InChl Key

XOXYHGOIRWABTC-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#:437-50-3) 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

18064621

Abstract

A novel, fast, and simple capillary electrophoresis method has been developed for the analysis of gentisin, isogentisin, and amarogentin in roots of Gentiana lutea (yellow gentian), an herb traditionally used as gastric stimulant. Gentisin and isogentisin are xanthones showing potent inhibition of monoamine oxidase type A and B, amarogentin represents one of the bitter principles of Gentiana, responsible for its gastric-roborant effects. Optimal CE-separation conditions comprise a 100 mM sodium tetraborate buffer of pH 9.3, containing 10 mM beta-cyclodextrin as additive; optimum temperature and applied voltage were found to be 30 degrees C and 25 kV, respectively. Direct diode array detection at 260 nm (gentisin, isogentisin) and 242 nm (amarogentin) was performed, and the required analysis time was only 11 min. The developed method was validated for linearity, sensitivity, precision, and accuracy, and utilized to assay several commercially available G. lutea samples. Quantitative data obtained with the developed CE method are compared with HPLC results, and the advantages of each approach are discussed.

Title

Determination of Gentisin, Isogentisin, and Amarogentin in Gentiana Lutea L. By Capillary Electrophoresis

Author

Ivana Citova 1 , Markus Ganzera, Hermann Stuppner, Petr Solich

Publish date

2008 Jan

PMID

6338357

Abstract

The mutagenic activities of 2 hydroxyxanthones, gentisin and isogentisin, obtained from the methanol extract of Gentianae radix (Gentianaceae) were investigated. The methanol extract of Gentianae radix, which showed mutagenicity in the Ames test in Salmonella typhimurium strain TA100 with S9 mix, was fractionated by column chromatography on Sephadex LH-20, and the fractions were purified by preparative TLC and column chromatography on polyamide. 2 mutagenic materials thus obtained, S1 and S2, each gave a single band on TLC. Identification of S1 and S2 was accomplished by comparing the analytical (mps, elementary analyses) and spectral (UV, IR, mass, NMR) results for S1 and S2 with literature data for gentisin and isogentisin. At doses below 10 micrograms, S1 (gentisin) and S2 (isogentisin) had similar specific mutagenic activities. At doses of over 10 to 50 micrograms, the mutagenic activities of S2 and S1 were 19.1 and 6.94 revertants per microgram respectively. This much lower activity of S1 than S2 may be a result of its poor solubility owing to the presence of the OMe group at C-3. The combined yield of S1 and S2 was about 76 mg (40 mg as S1 and 36 mg as S2), which accounted for 76% of the content of mutagenic compounds (100 mg) estimated roughly from the total mutagenic activity in the extract of the starting materials (100 g).

Title

Mutagenic Activities of Gentisin and Isogentisin From Gentianae Radix (Gentianaceae)

Author

I Morimoto, T Nozaka, F Watanabe, M Ishino, Y Hirose, T Okitsu

Publish date

1983 Feb

PMID

26580586

Abstract

Aberrant proliferation of vascular smooth muscle cells (VSMC) plays a major role in restenosis, the pathological renarrowing of the blood vessel lumen after surgical treatment of stenosis. Since available anti-proliferative pharmaceuticals produce unfavorable side effects, there is high demand for the identification of novel VSMC proliferation inhibitors. A natural product screening approach using a resazurin conversion assay enabled the identification of gentisin (1) from Gentiana lutea as a novel inhibitor of VSMC proliferation with an IC50 value of 7.84 µM. Aiming to identify further anti-proliferative compounds, 13 additional nonprenylated xanthones, isolated from different plant species, were also tested. While some compounds showed no or moderate activity at 30 µM, 1-hydroxy-2,3,4,5-tetramethoxyxanthone (4), swerchirin (6), and methylswertianin (7) showed IC50 values between 10.2 and 12.5 µM. The anti-proliferative effect of 1, 4, 6, and 7 was confirmed by the quantification of DNA synthesis (BrdU incorporation) in VSMC. Cell death quantification (determined by LDH release in the culture medium) revealed that the compounds are not cytotoxic in the investigated concentration range. In conclusion, nonprenylated xanthones are identified as novel, non-toxic VSMC proliferation inhibitors, which might contribute to the development of new therapeutic applications to combat restenosis.

KEYWORDS

Centaurium erythraea; Frasera caroliniensis; Gentiana lutea; Gentianaceae; atherosclerosis; bitter plants; gentisin; restenosis; vascular smooth muscle cell proliferation; xanthones..

Title

Nonprenylated Xanthones From Gentiana Lutea, Frasera Caroliniensis, and Centaurium Erythraea as Novel Inhibitors of Vascular Smooth Muscle Cell Proliferation

Author

Birgit Waltenberger 1 , Rongxia Liu 2 3 , Atanas G Atanasov 4 , Stefan Schwaiger 5 , Elke H Heiss 6 , Verena M Dirsch 7 , Hermann Stuppner 8

Publish date

2015 Nov 13