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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)
Y Tokura
Journal of dermatological science, 19(2), 114-122 (1999-03-31)
Modulatory effects on cytokine expression of 8-MOP in conjunction with UVA have been investigated in different systems using different cell types, including keratinocytes, lymphocytes, monocytes and endothelial cells. The vast majority of data have exhibited reduced production of cytokines in
Shujiro Hayashi et al.
Journal of dermatological science, 67(1), 20-25 (2012-04-11)
Recent studies have demonstrated that systemic or topical PUVA therapy, i.e., ultraviolet A (UVA) irradiation following treatment with 8-methoxypsoralen (8-MOP), is effective against the sclerotic skin lesions in systemic sclerosis. However, the mechanisms still remain unknown. To clarify the mechanisms
S Whittaker et al.
The British journal of dermatology, 167(3), 678-687 (2012-08-29)
Psoralen plus ultraviolet A (PUVA) is the standard treatment for early stages of mycosis fungoides. There have been no adequate randomized controlled trials with sufficient power comparing this modality with other therapies. To assess disease response and to compare the
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