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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O4
Molecular Weight 196.1999
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XANTHOXYLINE

SMILES

COC1=CC(OC)=C(C(C)=O)C(O)=C1

InChI

InChIKey=FBUBVLUPUDBFME-UHFFFAOYSA-N
InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3

HIDE SMILES / InChI
Molecular Formula C10H12O4
Molecular Weight 196.1999
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Xanthoxyline is a naturally occurring plant metabolite which can be extracted from the several plants in the Euphorbiaceae family which are commonly used in folk medicines. Isolated Xanthoxyline has demonstrated fungicidal and fungistatic activity. Some synthetic derivatives of Xanthoxyline have demonstrated degrees of anti-nocioceptive properties.

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Phenols from Euphorbia humifusa].
2010-03
Antinociceptive and anti-inflammatory effects of ethanolic extracts of Glycine max (L.) Merr and Rhynchosia nulubilis seeds.
2009-11-04
Antimicrobial phenolic compounds from Anabasis aphylla L.
2009-03
Pharmacokinetics and tissue distribution of 8,9-epoxy brevifolin in rats, a hepatoprotective constituent isolated from Phyllanthus simplex Retz by liquid chromatography coupled with mass spectrometry method.
2008-07
[Chemical constituents of aerial part of Acalypha australis].
2008-06
[Protecting effect of brevifolin and 8,9-single-epoxy brevifolin of Phyllanthus simplex on rat liver injury].
2006-09
[Studies on chemical constituents in roots of Euphorbia soongarica].
2006-09
Antinociceptive effects of synthetic chalcones obtained from xanthoxyline.
2006-07
Molecular structure and QSAR study on antispasmodic activity of some xanthoxyline derivatives.
2006-05
Synthesis of chalcone analogues with increased antileishmanial activity.
2006-03-01
Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones.
2005-03
Antifungal constituents of Melicope borbonica.
2004-07
A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi.
2003-09
Frontal immunoaffinity chromatography with mass spectrometric detection: a method for finding active compounds from traditional Chinese herbs.
2003-08-15
Antibacterial alkaloids from Zanthoxylum rhoifolium.
2003-04
Phenolic acids and depsides from some species of the Erodium genera.
2002-02-12
Antifeedant constituents from Fagara macrophylla.
2001-06
Fungicide and fungiostatic effects of xanthoxyline.
1996-09
Patents

Patents

05234951
3
20060074108
2
US20100048729 A1
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Microorganisms including Candida albicans (FCF-243 and ICB-12), C. tropicalis, C. neoformans, Microsporum canis (LM-003 and 72-T), Trichophytom rubrum (54-T and 45 T), T. mentagrophytes, Epidermophyton floccosum, Aspergillus flavus (FCF-29), A. parasiticus and Penicillium sp were tested against xanthoxyline by method of successive dilution. Xanthoxyline was solubilized in DMSO and diluted with Sabouraud liquor. Test cultures were incubated at 28 - 30 deg-C for 10 - 14 days. Xanthoxyline proved particularly efficacious against M. canis 72-T and T. rubrum 45-T with minimal inhibitory concentrations MIC of 31.2 and 62.5 micro-g/mL respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:22:07 GMT 2025
Edited
by admin
on Mon Mar 31 21:22:07 GMT 2025
Record UNII
Z8RSY5TZPA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BREVIFOLIN
Preferred Name English
XANTHOXYLINE
Common Name English
PHLOROACETOPHENONE DIMETHYL ETHER
Common Name English
NSC-17392
Code English
Xanthoxyline [WHO-DD]
Common Name English
2',4'-DIMETHOXY-6'-HYDROXYACETOPHENONE
Systematic Name English
XANTHOXYLIN [MI]
Common Name English
PHLOROACETOPHENONE 2,4-DIMETHYL ETHER
Common Name English
2,4-DI-O-METHYLPHLOROACETOPHENONE
Common Name English
2-ACETYL-3,5-DIMETHOXYPHENOL
Systematic Name English
2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE
Systematic Name English
1-ACETYL-2-HYDROXY-4,6-DIMETHOXYBENZENE
Systematic Name English
4',6'-DIMETHOXY-2'-HYDROXYACETOPHENONE
Systematic Name English
1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)ETHANONE
Systematic Name English
Code System Code Type Description
CAS
90-24-4
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID10237981
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
PUBCHEM
66654
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
SMS_ID
300000005508
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-978-3
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
FDA UNII
Z8RSY5TZPA
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
WIKIPEDIA
Brevifolin
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
MERCK INDEX
m11535
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY Merck Index
NSC
17392
Created by admin on Mon Mar 31 21:22:07 GMT 2025 , Edited by admin on Mon Mar 31 21:22:07 GMT 2025
PRIMARY
NIH
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