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Methoxsalen CAS 298-81-7 Xanthotoxin

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  • Appearance: White powder
  • Purity: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Methoxsalen Supplier & Manufacturer

Basic Info

What is Methoxsalen?

Xanthotoxin is a natural compound of furanocoumarins with strong photosensitivity, also known as 8-methoxypsoralen, whose appearance is fine needle-like crystals (hot water or benzene-petroleum ether) or square prism crystals ( Alcohol-ether), odorless, bitter and irritating, soluble in chloroform, soluble in boiling alcohol, acetone, acetic acid, benzene, vegetable oil, propylene glycol, slightly soluble in boiling water, ether and liquid paraffin, insoluble in cold water. Ring-opening in alkaline aqueous solution, and ring-closing after neutralization.

Xanthotoxin was first isolated from the fruit of Ammimajus L., and now it is mainly found in plants such as Umbelliferae and Rutaceae. Clinically abroad, it is mainly used for the treatment of chronic skin diseases such as vitiligo and psoriasis with psoralen compounds plus ultraviolet light therapy (PUVA). In recent years, it has been found that xanthotoxin has a good inactivation effect on a variety of DNA viruses and RNA viruses in the blood, and can also induce tumor cell apoptosis.

Zanthoxylum toxin is a natural compound of furanocoumarins with various pharmacological effects. It is also a plant toxin, which is more commonly found in seasonings such as pepper and star anise. Long-term and large-scale consumption can cause poisoning and darken the skin role. Like aflatoxin, it has double bonds on coumarin lactone and furan ring, and is a potential carcinogen.

Methoxsalen Uses

  • A natural analogue of Psoralen (P839800). Made use of for the therapy of psoriasis and also mycosis fungoides.
  • Methoxsalen can induce single adduct and interchain cross-linking in DNA with UVA irradiation to study the mechanism of DNA repair and recombination.
  • Zanthoxylum toxin has spasmolytic and antibacterial effects. Toxic to fish. Clinically used to treat angina, vitiligo, psoriasis, and psoriasis. In addition, it can also be used as a colorant and as a pigment forming agent.
  • Methoxsalen has the very same effect as Trioxalin. Methoxsalen transcends to Trioxalin in producing erythema as well as sun tanning, and is utilized in PUVA treatment. Methoxsalen additionally has 1% cream.
  • 8-Methodypsoralen, made use of for photochemical therapy (methodsalen with lengthy wave ultraviolet radiation), for re staining of idiopathic leukoplakia. It is additionally utilized for Photopheresis (lengthy wave ultraviolet radiation of methoxsalen as well as leukocytes), which appropriates for palliative treatment of skin indications of cutaneous T-cell lymphoma along with UVAR * system.

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Application of Methoxsalen

Zanthoxylum toxin has the effects of resisting experimental arrhythmia, analgesia, anti-inflammation, relaxing rat uterus, rabbit ileum and vascular smooth muscle, and inhibiting guinea pig heart. The research results show that XAT relaxes smooth muscle mainly by blocking the calcium channels of rat uterus, rabbit ileum and vascular smooth muscle cells. The automaticity of the atrial node suggests that XAT may play a role by affecting the Ca2+ transport of cardiomyocytes. As a photosensitizer, the toxin can be used in combination with long-wave ultraviolet rays for photochemotherapy in the treatment of psoriasis, which has become one of the internationally recognized treatment methods. There are two routes of administration: oral or local lesions. The common side effects of oral administration of this therapy are pigmentation, dizziness, erythema, itching, nausea and the risk of cataracts and skin tumors after long-term application. Its metabolism in animals has been reported. It is absorbed through the gastrointestinal tract, and its blood concentration can reach a peak after 1 hour. The biological half-life is 6 hours. It is mainly distributed in the skin and liver, especially in the skin.

Preparation of Methoxsalen

Compound 8-geranioxypsoralen has been found to exist in citrus oil, especially in lemon oil and lime oil. This compound can be separated from oil by a method that involves first adsorbing onto the adsorbent material and then eluting with a suitable solvent.

  • Cracking of 8-Geranoxypsoralen: 275 mg of 8-Geranoxypsoralen was dissolved in 4 ml of glacial acetic acid under mechanical stirring. After 10 minutes, add one drop of concentrated sulfuric acid to the solution. After 4 minutes, a light brown precipitate begins to form. Continue stirring for 35 minutes and refrigerate the reaction mixture for 1 hour and 20 minutes. Then remove the sediment through suction filtration and wash with glacial acetic acid on the filter, followed by washing with cold ether. The weight of product 8-hydroxypsoralen is 115 milligrams, which is 74% of the theoretical value.
  • Methylation of 8-hydroxypsoralen: Dissolve 115mg of 8-hydroxypsoralen in 10ml of anhydrous methanol, add excess diazomethane dissolved in ether, and let the mixture stand at room temperature for 3 hours, occasionally stirring. The next day, the volume of the reaction mixture was reduced to 3ml by evaporation on a steam bath, and the concentrate was placed overnight in the refrigerator. The next day, filter out a fine needle (80 mg) of 8-methoxypsoralen from the solution. The melting point of this compound is 145 to 146 ° C, and the yield is 65% of the theoretical value.

Reference

  1. Methoxsalen – WikiPedia
  2. Fahmy IR, Abu-Shady H (1947). “Ammi majus Linn.; pharmacognostical study and isolation of a crystalline constituent, ammoidin”. Quarterly Journal of Pharmacy and Pharmacology

Methoxsalen Supplier and Manufacturer

As a methoxsalen supplier and manufacturer with a strict standard product quality system certificate, Zhishang Chemical has long been providing the best methoxsalen raw materials to customers all over the world.

Over the years, relying on professional team experience and customer-centric team concept to meet customer needs in a timely manner, our company enjoys a high reputation in the world. At present, our company has served more than 6,000 customers and has established long-term cooperative relations with customers from many countries.

If you have a demand for methoxsalen and related products, please contact our service staff Zhishang Chemical – White directly, and we will provide you with high-quality products at the best price.

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