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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14O4
Molecular Weight 258.2693
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XANTHOXYLETIN

SMILES

COC1=C2C=CC(C)(C)OC2=CC3=C1C=CC(=O)O3

InChI

InChIKey=JSJIIHRNDMLJGK-UHFFFAOYSA-N
InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3

HIDE SMILES / InChI
Xanthoxyletin is a coumarin isolated from Erythrina variegata. It has been reported that Xanthoxyletin possesses antibacterial, fungicidal, and algicidal properties. Xanthoxyletin induces S phase arrest and apoptosis in human gastric adenocarcinoma SGC-7901 cells. Xanthoxyletin may be promising anticancer agent and has worth for further mechanistic and therapeutic studies against gastric cancer.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic coumarins and lignans from extracts of the northern prickly ash (Zanthoxylum americanum).
2001 Aug
[Studies on the coumarins in the root of Zanthoxylum dimorphophyllum].
2003 Apr
Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion.
2003 Apr 16
Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities.
2003 Feb
Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica.
2003 Feb
Separation and determination of coumarins in the root bark of three citrus plants by micellar electrokinetic capillary chromatography.
2003 May
Chemical characterization of Citrus sinensis grafted on C. limonia and the effect of some isolated compounds on the growth of Xylella fastidiosa.
2008 Sep 10
Anti-HBV and cytotoxic activities of pyranocoumarin derivatives.
2009 Aug 15
Inhibitory effect of oxycoumarins isolated from the Thai medicinal plant Clausena guillauminii on the inflammation mediators, iNOS, TNF-alpha, and COX-2 expression in mouse macrophage RAW 264.7.
2009 Jan
Isolation of xanthyletin, an inhibitor of ants' symbiotic fungus, by high-speed counter-current chromatography.
2009 May 8
Antimicrobial coumarins from the stem bark of Afraegle paniculata.
2010 Apr
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
After treating the SGC-7901 cells with 200 and 400 uM of Xanthoxyletin for 48 h, ROS production was detected and the ratios of DCF-positive cells were 18.66% and 32.86% respectively as compared to 8.27% in the control group. Xanthoxyletin induced apoptosis in SGC-7901 cells and percentage of apoptotic cells was 41.47% after the exposure of 400 uM of Xanthoxyletin for 48 h as compared to 2.6% in the control group.
Name Type Language
XANTHOXYLETIN
MI  
Common Name English
7-HYDROXY-5-METHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE
Common Name English
NSC-35542
Code English
XANTHOXYLIN N
Common Name English
XANTHOXYLETIN [MI]
Common Name English
XANTHOXYLOIN
Common Name English
Code System Code Type Description
CAS
84-99-1
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID70232891
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY
PUBCHEM
66548
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY
MERCK INDEX
m11534
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY Merck Index
MESH
C477468
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY
FDA UNII
69MPX4M5VD
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY
NSC
35542
Created by admin on Fri Dec 15 19:44:30 GMT 2023 , Edited by admin on Fri Dec 15 19:44:30 GMT 2023
PRIMARY