We Offer Worldwide Shipping
Login Wishlist

Xanthotoxin

$53

  • Brand : BIOFRON

  • Catalogue Number : AV-P11380

  • Specification : 98%

  • CAS number : 298-81-7

  • Formula : C12H8O4

  • Molecular Weight : 216.19

  • PUBCHEM ID : 4114

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

AV-P11380

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

216.19

Appearance

White crystalline powder

Botanical Source

Fagava zanthoxyloides Lam./Cnidium dubium, Cryptodiscus didymus (preferred genus name Prangos), Evodia hupehensis, Selinum tenuifolium, Aegle marmelos, Xanthoxylum senegalense, Psoralea sp., Ruta graveolens, Heracleum sp., Ammi majus, Limonia acidissima, Glehnia littor

Structure Type

Coumarins

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2

Synonyms

8-MP/Puvalen/Xanthotoxin/Methoxsalen/Puvamet/Dermox/Meloxine/7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-/Vitpso/Meladinine/Deltasoralen/OXSORALEN/9-methoxypsoralen/8-methoxypsoralene/8-MOP,9-Methoxyfuro[3,2-g][1]benzopyran-7-one,Ammoidin/Uvadex/9-Methoxy-7H-furo[3,2-g]chromen-7-one/Ammodin/8-MOP/8-MOP,8-Methoxypsoralen,9-Methoxyfuro[3,2-g][1]benzopyran-7-one/Methoxsalen, 8-/6-Hydroxy-7-methoxy-5-benzofuranacrylic Acid d-Lactone/8-Methoxypsoralen/Metoxin/8-Methoxy[furano-3',2':6,7-coumarin]

IUPAC Name

9-methoxyfuro[3,2-g]chromen-7-one

Applications

Methoxsalen (8-Methoxypsoralen) is a potent tricyclic furocoumarin suicide inhibitor of CYP (cytochrome P-450), is an agent used to treat psoriasis, eczema, vitiligo and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight.Target: CYP (cytochrome P-450)Methoxsalen is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to UVA light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10 mg tablets, which are taken in the amount of 30 mg 75 minutes before a PUVA (psoralen + UVA) light treatment. Chemically, methoxsalen belongs to a class of organic natural molecules known asfuranocoumarins. They consist of coumarin annulated with furan.Administration of intra peritoneal (ip) methoxsalen significantly increased nicotine's Cmax, prolonged the plasma half-life (fourfold decrease) of nicotine, and increased its area under the curve (AUC) compared with ip vehicle treatment. Methoxsalen pretreatment prolonged the duration of nicotine-induced antinociception and hypothermia (15mg/kg, po) for periods up to 6- and 24-hr postnicotine administration, respectively.

Density

1.4±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

204.7±28.7 °C

Boiling Point

414.8±45.0 °C at 760 mmHg

Melting Point

143-148 ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:298-81-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

18523826

Abstract

Plant chemistry can have deleterious effects on insect parasitoids, which include the reduction in body size, increased development time, and increased mortality. We examined the effects of xanthotoxin, a linear furanocoumarin, on the polyembryonic encyrtid wasp Copidosoma sosares, a specialist parasitoid that attacks the parsnip webworm, Depressaria pastinacella, itself a specialist on furanocoumarin-producing plants. Furanocoumarins, allelochemicals abundant in the Apiaceae and Rutaceae, are toxic to a wide range of herbivores. In this study, we reared parasitized webworms on artificial diets containing no xanthotoxin (control) or low or high concentrations of xanthotoxin. Clutch sizes of both male and female C. sosares broods were more than 20% smaller when they developed in hosts fed the diet containing high concentrations of xanthotoxin. Xanthotoxin concentration in the artificial diet had no effect on the development time of C. sosares, nor did it have an effect on the body size (length of hind tibia) of individual adult male and female C. sosares in single-sex broods. Webworms fed artificial diets containing low or high concentrations of xanthotoxin were not significantly smaller, and their development time was similar to that of webworms fed a xanthotoxin-free diet. Mortality of webworms was not affected by xanthotoxin in their artificial diet. Therefore, dietary xanthotoxin did not appear to affect C. sosares via impairment of host health. However, unmetabolized xanthotoxin was found in D. pastinacella hemolymph where C. sosares embryos develop. Hemolymph concentrations were fourfold greater in webworms fed the high-xanthotoxin-containing diet than in webworms fed the low-xanthotoxin-containing diet. We failed to detect any xanthotoxin metabolism by either C. sosares embryos or precocious larvae. Therefore, the observed tritrophic effects of xanthotoxin are likely to be due to the effects of xanthotoxin after direct contact in the hemolymph rather than to the effects of compromised host quality.

Title

Tritrophic Effects of Xanthotoxin on the Polyembryonic Parasitoid Copidosoma Sosares (Hymenoptera: Encyrtidae)

Author

Evan C Lampert 1 , Arthur R Zangerl, May R Berenbaum, Paul J Ode

Publish date

2008 Jun

PMID

16572296

Abstract

Within the genus Papilio, the P. glaucus group contains the most polyphagous Papilio species within the Papilionidae. The majority of Papilio species are associated with hostplants in the families Rutaceae and Apiaceae, and characterizing most are secondary metabolites called furanocoumarins. Recent phylogenetic studies suggest that furanocoumarin metabolism is an ancestral trait, with the glaucus group derived from ancestors associated with furanocoumarin-containing Rutaceae. In this study, we examined this relationship by conducting a gravimetric analysis of growth that used various concentrations of the furanocoumarin xanthotoxin. Papilio multicaudatus, the putative ancestor of the glaucus group, includes at least one furanocoumarin-containing rutaceous species among its hostplants; this species can consume leaf tissue containing up to 0.3% xanthotoxin with no detectable effect on relative growth rate, relative consumption rate, or efficiency of conversion of ingested food. As is the case for other Papilio species, xanthotoxin metabolism is mediated by cytochrome P450 monooxygenases (P450s). Ingestion of xanthotoxin by ultimate instar P. multicaudatus increases activity up to 30-fold in a dose-dependent fashion. Midguts of induced larvae can also effectively metabolize six other furanocoumarins, including both linear (bergapten, isopimpinellin, imperatorin) and angular (angelicin, sphondin) forms. A metabolite of xanthotoxin in the frass from xanthotoxin-treated larvae, identified as 6-(7-hydroxy-8-methoxycoumaryl)-acetic acid by MS-MS and NMR analyses, is identical to one from the frass of P. polyxenes. The occurrence of this metabolite in two swallowtails and the presence of a second metabolite of xanthotoxin, 6-(7-hydroxy-8-methoxycoumaryl)-hydroxyethanol in the frass of both P. polyxenes and Depressaria pastinacella are consistent with the suggestion that lepidopterans share as the first step of xanthotoxin metabolism the P450-mediated epoxidation of the furan ring 2′-3′ double bond.

Title

Cytochrome P450-mediated Metabolism of Xanthotoxin by Papilio Multicaudatus

Author

Wenfu Mao 1 , Mark A Berhow, Arthur R Zangerl, Jennifer McGovern, May R Berenbaum

Publish date

2006 Mar

PMID

14658506

Abstract

Cytochrome P450 monooxygenases (P450) are membrane-bound hemoproteins that play important roles in conferring protection against both naturally occurring phytochemicals and synthetic organic insecticides. Despite the potential for common modes of detoxification, cross-resistance between phytochemicals and synthetic organic insecticides has rarely been documented. In this study, we examined the responses of a susceptible strain of corn earworm, Helicoverpa zea (Boddie), a polyphagous noctuid, to exposure by an allelochemical infrequently encountered in its host plants and by an insecticide widely used for control purposes. Within a single generation, survivors of xanthotoxin exposure displayed higher levels of tolerance to alpha-cypermethrin than did unexposed control larvae. The F1 offspring of xanthotoxin-exposed survivors also displayed higher alpha-cypermethrin tolerance than did offspring of unexposed control larvae, suggesting that increased alpha-cypermethrin tolerance after xanthotoxin exposure represents, at least in part, heritable resistance. Administration of piperonyl butoxide, a P450 synergist, demonstrated that resistance to both xanthotoxin and alpha-cypermethrin is P450-mediated. Alpha-cypermethrin-exposed survivors, however, failed to show superior growth on xanthotoxin diets. Assays with control larvae, larvae induced by both xanthotoxin and alpha-cypermethrin, and survivors of LD50 doses of both compounds indicated that H. zea midgut P450s are capable of metabolizing both xanthotoxin and alpha-cypermethrin. Metabolism of each compound is significantly inhibited by the presence of the other compound, suggesting that at least one form of P450 in H. zea midguts degrades both compounds and may constitute the biochemical basis for possible cross-resistance. Compared with control larvae, xanthotoxin- and alpha-cypermethrin-induced larvae displayed 2- to 4-fold higher P450-mediated metabolism of both compounds. However, xanthotoxin- and alpha-cypermethrin-exposed survivors exhibited much higher (2.5- to 11-fold) metabolism of both compounds than did the induced larvae. The metabolism results, like the bioassay results, are consistent with the interpretation that increased alpha-cypermethrin tolerance after xanthotoxin exposure is attributable mainly to heritable resistance.

Title

Cross-resistance to Alpha-Cypermethrin After Xanthotoxin Ingestion in Helicoverpa Zea (Lepidoptera: Noctuidae)

Author

X Li 1 , A R Zangerl, M A Schuler, M R Berenbaum

Publish date

2000 Feb