56448
Xanthotoxin
analytical standard
Synonym(s):
8-Methoxypsoralen, 8-MOP, 9-Methoxyfuro[3,2-g][1]benzopyran-7-one, Ammoidin, Methoxsalen, Xanthotoxin
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About This Item
Empirical Formula (Hill Notation):
C12H8O4
CAS Number:
Molecular Weight:
216.19
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
EC Number:
206-066-9
Beilstein/REAXYS Number:
196453
MDL number:
Quality Level
grade
analytical standard
assay
≥98% (GC)
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable, gas chromatography (GC): suitable
mp
148-150 °C (lit.)
application(s)
cleaning products
cosmetics
food and beverages
personal care
format
neat
storage temp.
2-8°C
SMILES string
COc1c2OC(=O)C=Cc2cc3ccoc13
InChI
1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChI key
QXKHYNVANLEOEG-UHFFFAOYSA-N
General description
Xanthotoxin is an allelochemical or a phototoxic allomone mainly found in host plants of black swallowtail. It can have the tendency to induce tolerance towards Α-cypermethrin, a pyrethroid insecticide used for insects like Helicoverpa zea.
Application
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Biochem/physiol Actions
8-methoxypsoralen (8-MOP) plus ultraviolet A (UVA) irradiation induces monoadducts and interstrand cross-links in DNA and therefore can be used to study DNA repair and recombination mechanisms. Cultured normal human melanocytes treated with 8-methoxypsoralen and irradiated with ultraviolet A (UVA) formed 8-methoxypsoralen-phospholipid photoadducts that could be substituted for diacylglycerol to activate protein kinase C in a cell-free system. 8-MOP is an inactivator of purified reconstituted cytochrome P450. It also inhibits substance P-induced histamine release from substance P-activated rat peritoneal mast cells by suppressing the rise in [Ca2+].
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
This compound is commonly found in plants of the genus: angelica carum pimpinella
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Muta. 2 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Molecular cloning and expression of CYP6B8: a xanthotoxin-inducible cytochrome P450 cDNA from Helicoverpa zea
Li X, et al.
Insect Biochemistry and Molecular Biology, 30, 75-84 (2000)
Induction of cytochrome P450-mediated detoxification of xanthotoxin in the black swallowtail
Cohen.BM, et al.
Journal of Chemical Ecology, 15, 2347-2355 (1989)
Franz Trautinger et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 12(1), 22-28 (2012-08-04)
Photopheresis is a form of phototherapy where specialized equipment is used to isolate a leukocyte fraction from the peripheral blood which is then exposed to photoactivated 8-methoxypsoralen and reinfused into the patient. At the time of its invention the treatment