ChemicalBook > Product Catalog > Pharmaceutical intermediates > Heterocyclic compound > Pyran compounds > Bergapten
Bergapten Chemical Properties
- Melting point:190-193 °C(lit.)
- Boiling point:276.6°C (rough estimate)
- Density 1.1344 (rough estimate)
- refractive index 1.4270 (estimate)
- storage temp. 2-8°C
- form neat
- Merck 14,1157
- BRN 19560
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.
- CAS DataBase Reference484-20-8(CAS DataBase Reference)
- NIST Chemistry Reference7H-furo[3,2-g]benzopyran-7-one, 4-methoxy-(484-20-8)
- IARC2A (Vol. 40, Sup 7) 1987
- EPA Substance Registry System5-Methoxypsoralen (484-20-8)
Bergapten Usage And Synthesis
- DescriptionBergapten exists in roots, stems, and leaves of a variety of Rutaceae, Umbelliferae, and leguminous plants such as ephedra, fennel, and vetch.
- Chemical PropertiesCrystalline Solid
- Physical propertiesAppearance: Crystalline state is mercerizing white needled crystal. Autofluorescence can be observed under the excitation of UV at 432?nm. By directly adding bergapten into sulfuric acid, the solution became golden. Because of the structure of coumarin lactone, hydroxamic acid iron reaction can be occurred. Solubility: It is soluble in chloroform; slightly soluble in benzene, ethyl acetate, and ethanol; and insoluble in water. It has a photosensitive activity. Crystalline state is mercerizing white needled crystal. Melting point: 181–183?°C.
- HistoryIt was first isolated from a plant called Ammi majus L in 1947. It was first synthesized by JEAN and JACQUES in 1982. The efficacy of psoralen in the treatment of psoriasis and other skin diseases has been studied in modern medicine, and more and more studies have proven that the extracts and derivatives of psoralen have significant effect on the treatment of various skin diseases. Bergapten used in the treatment of PUVA (psoralen plus ultraviolet) and treatment of vitiligo has more than 20?years of history. 8-Methoxypsoralen in the treatment of psoriasis frequently has a problem of phototoxicity and drug intolerance. Therefore, researchers have studied 5-MOP (5-methoxypsoralen) on this basis. The results showed that the 5-methoxypsoralen has a close effect and fewer side effects of the treatment companies with the 8-methoxypsoralen with a double dose.
- UsesNaturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic
- UsesHas been used to promote tanning in suntan preparations.
- Usesantipsoriatic, antiinflammatory
- UsesNaturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.
- UsesA psoralen phytotoxic citrus essential oil found in bergamont
- DefinitionChEBI: A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.
- General DescriptionGrayish-white microcrystalline powder or yellow fluffy solid.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileBergapten may be sensitive to exposure to light. A related chemical is incompatible with strong oxidizers.
- Fire HazardFlash point data for Bergapten are not available; however, Bergapten is probably combustible.
- Contact allergensThis fur(an)ocoumarin is an phototoxic compound that causes phototoxic dermatitis. Many plants of the Apiaceae–Umbelliferae and most of the Rutaceae family contain 5-methoxypsoralen and 8-methoxypsoralen. Their spectra is in the UVA range (300–360 nm). It is used in combination with UVA to treat various skin disorders such as psoriasis.
- PharmacologyBergapten could be used to treat vitiligo mainly because it can be embedded between the thymine base pairs of DNA in darkness. Under UV light (365?nm) double furan ring or pyran ring on the irradiation can occur halo reaction showed the structure and biological activity of thymine. The curative effect of high-dose 5-MOP (1.2–1.6?mg/kg) in the treatment of UVA is better and has a less cure time.
As the main component of the drug, it can be used to treat different types of psoriasis.
The study of Shikishima et al. showed that the bergapten has an anti-HIV activity, which was mainly affected by HIV reverse transcriptase, protease, and integrase, and the IC50 value was 24.8 mg/L.
Modern pharmacological studies have shown that it has a certain inhibitory activity on tumor and cell proliferation.
- Clinical UseIt has the optical activity to the skin, has the function of killing the soft animal, has the anticoagulant function and the hemostatic effect against the heparin, and has the antimicrobial activity. In a trial for chemical therapy in the treatment of psoriasis patients, the result has shown that the drug can stimulate the melanin and increase the skin pigmentation, which is essential for the treatment of vitiligo.
- Purification MethodsCrystallise it from EtOH or aqueous MeOH, and it sublimes in vacuo. Its properties are similar to those of its 9-methoxy isomer (xanthotoxin, see below). It is slightly soluble in *C6H6, CHCl3 and AcOH but insoluble in H2O. Its fluorescence has ex at 352nm with em at 480nm. It is a DNA intercalator and possible carcinogen. [Howell & Robertson J Chem Soc 293 1937, Boyer et al. Biochemistry 27 3011 1988, Beilstein 19/6 V 4.]
Bergapten Preparation Products And Raw materials
- Raw materialsSodium hydroxideHydrochloric acidEthyl acetateMethanolSulfuric acid DichloromethaneN,N-DimethylformamidePotassium carbonateChloroformSodium sulfateTriethylamineAmmoniaSodium bicarbonate1,4-DioxaneFormic acidtert-ButanolZinc chloridePotassium iodideIodineTetrabutylammonium bromideBoron trifluoride etheratePalladium diacetate2,6-LutidineAllyl bromideSodium periodateOsmium tetraoxideEthyl propiolatePhloroglucinol dihydrate
- BERGAPTEN(SH) 5-METHOXYPSORALEN (BERGAPTEN) AKOS 211-03 BERGAMOTTIN [ALL TRANS GERANYL-1-14C] BYAKANGELICIN AKOS 244-100 BYAKANGELICIN Isoimperatorin phellopterin ISOOXYPEUCEDANIN OXYPEUCEDANIN HYDRATE 4-Methoxybenzylchloride 3-Methoxybenzaldehyde 4-Methoxyphenylacetone Spironolactone Methoxy (Trifluoromethoxy)benzene Furazolidone
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