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Xanthotoxin

analytical standard

Synonyme(s) :

8-Methoxypsoralen, 8-MOP, 9-Methoxyfuro[3,2-g][1]benzopyran-7-one, Ammoidin, Methoxsalen, Xanthotoxin

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About This Item

Formule empirique (notation de Hill):
C12H8O4
Numéro CAS:
298-81-7
Poids moléculaire :
216.19
Numéro Beilstein :
196453
Numéro CE :
206-066-9
Numéro MDL:
MFCD00005009
Code UNSPSC :
85151701
ID de substance PubChem :
329758209
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

100

Pureté

≥98% (GC)

Durée de conservation

limited shelf life, expiry date on the label

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Pf

148-150 °C (lit.)

Application(s)

cleaning products
cosmetics
food and beverages
personal care

Format

neat

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

QXKHYNVANLEOEG-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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+].

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

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

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H317,H341,H351

Classification des risques

Acute Tox. 4 Oral - Carc. 2 - Muta. 2 - Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
BCCF2413
BCBZ7331
BCBS5595V
BCBQ4358V
BCBL4929V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
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
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
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
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