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Merck
CN

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:
298-81-7
Molecular Weight:
216.19
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329758209
EC Number:
206-066-9
Beilstein/REAXYS Number:
196453
MDL number:
MFCD00005009

Key Documents

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Product Name

Xanthotoxin, analytical standard

SMILES string

COc1c2OC(=O)C=Cc2cc3ccoc13

InChI key

QXKHYNVANLEOEG-UHFFFAOYSA-N

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

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

Quality Level

100

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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+].

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.

Other Notes

This compound is commonly found in plants of the genus: angelica carum pimpinella

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

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

Regulatory Information

高风险级别生物产品--毒素类产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5791
BCCH2520
BCCF2413
BCBZ7331
BCBS5595V

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Induction of cytochrome P450-mediated detoxification of xanthotoxin in the black swallowtail
Cohen.BM, et al.
Journal of Chemical Ecology, 15, 2347-2355 (1989)
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)
Yan Peng et al.
Toxicology, 301(1-3), 58-65 (2012-07-17)
8-Methoxypsoralen (8-MOP), a naturally occurring compound, is a potent modulator of epidermal cell growth and differentiation in combination with ultraviolet light. However, there is little information on 8-MOP contribution to cell apoptosis alone. In the study, we evaluated 8-MOP, independently
Tej Pratap Singh et al.
Experimental dermatology, 21(3), 228-230 (2012-03-03)
8-Methoxypsoralen plus UVA (PUVA) photochemotherapy is an effective treatment for many skin diseases including psoriasis. However, its exact mechanism of therapeutic action is incompletely understood. Previously, in K5.hTGFβ1 transgenic psoriatic mice, we found that PUVA induces Foxp3+ CD25+ CD4+ regulatory T cells
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
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