484-20-8

Basic information

• Product Name: Bergapten
• Synonyms: 2-g)(1)benzopyran-7-one,4-methoxy-7h-furo(;4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one;4-methoxy-7H-furo[3,2-g][1]benzopyran-7-one;4-Methoxy-7H-furo[3,2-g]chromen-7-one;4-Methoxy-furo[3,2-g]chromen-7-one;5-Methoxy-6,7-furanocoumarin;6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactone;6-hydroxy-4-methoxy-5-benzofuranacrylicacid,gamma-lactone
• CAS NO: 484-20-8
• Molecular Formula: C12H8O4
• Molecular Weight: 216.19
• EINECS: 207-604-5
• Product Categories: Coumarins;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles;Metabolites & Impurities;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;PSORADERM-5;Inhibitors
• Mol File: 484-20-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 190-193 °C(lit.)
• Boiling Point: 276.6°C (rough estimate)
• Flash Point: 203.2 °C
• Appearance: Crystalline solid
• Density: 1.1344 (rough estimate)
• Vapor Pressure: 5.2E-07mmHg at 25°C
• Refractive Index: 1.4270 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.
• Merck: 14,1157
• BRN: 19560
• CAS DataBase Reference: Bergapten(CAS DataBase Reference)
• NIST Chemistry Reference: Bergapten(484-20-8)
• EPA Substance Registry System: Bergapten(484-20-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 43-45
• Safety Statements: 36/37-45-53
• WGK Germany: 2
• RTECS: LV1300000
• F: 8-10
• Hazardous Substances Data: 484-20-8(Hazardous Substances Data)

Usage

Description

Bergapten exists in roots, stems, and leaves of a variety of Rutaceae, Umbelliferae, and leguminous plants such as ephedra, fennel, and vetch.

Chemical Properties

Crystalline Solid

Physical properties

Appearance: 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.

History

It 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.

Uses

Different sources of media describe the Uses of 484-20-8 differently. You can refer to the following data:
1. Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic
2. Has been used to promote tanning in suntan preparations.
3. antipsoriatic, antiinflammatory
4. Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.
5. A psoralen phytotoxic citrus essential oil found in bergamont

Definition

ChEBI: A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.

General Description

Grayish-white microcrystalline powder or yellow fluffy solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Bergapten may be sensitive to exposure to light. A related chemical is incompatible with strong oxidizers.

Fire Hazard

Flash point data for Bergapten are not available; however, Bergapten is probably combustible.

Pharmacology

Bergapten 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 Use

It 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 Methods

Crystallise 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.]

InChI:InChI=1/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

Synthetic route

9-iodo-5-methoxyfurano[3,2-g]chromen-2-one (122850-55-9) → bergapten (484-20-8)

Conditions	Yield
With formic acid; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 11h;	90%

5-methoxy-7-(2-oxoethoxy)coumarin → bergapten (484-20-8)

Conditions	Yield
With sodium hydroxide for 4h; Heating;	40%

Upstream product

• 486-60-2 bergaptol 
• 77-78-1 dimethyl sulfate 
• 866081-73-4 7-(2,3-dihydroxypropoxy)-8-iodod-5-methoxychromen-2-one 
• 866081-74-5 2-(8-iodo-5-methoxy-2-oxochromen-7-yloxy)ethanal 
• 122850-55-9 9-iodo-5-methoxyfurano[3,2-g]chromen-2-one 
• 186581-53-3 diazomethane 
• 482-44-0 imperatorin 
• 131623-13-7 bergaptol-O-β-D-glucopyranoside 
• 78045-69-9 8-iodo-5-methoxy-7-prop-2-enyloxychromen-2-one 
• 74794-29-9 7-hydroxy-8-iodo-5-methoxychromene-2-one 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 2174-64-3 5-methoxyresorcinol 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 108-73-6 3,5-dihydroxyphenol 
• 3067-09-2 6-formyl-7-hydroxy-5-methoxycoumarin 
• 1426427-48-6 C₁₉H₁₂O₆ 
• 1426427-49-7 C₂₁H₁₄O₆ 
• 1426427-50-0 C₂₅H₂₂O₆ 
• 1426427-47-5 4-(5-methoxypsoralen-8-yl)benzaldehyde 
• 96990-02-2 4-Methoxy-7-oxo-7H-furo[3,2-g]chromene-9-sulfonic acid [4-(4,6-dimethyl-pyrimidin-2-ylsulfamoyl)-phenyl]-amide 
• 96961-04-5 4-Methoxy-7-oxo-7H-furo[3,2-g]chromene-9-sulfonic acid [4-(3-methyl-isoxazol-5-ylsulfamoyl)-phenyl]-amide 
• 96944-55-7 4-Methoxy-7-oxo-7H-furo[3,2-g]chromene-9-sulfonic acid [4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-amide 
• 96944-36-4 4-Methoxy-7-oxo-7H-furo[3,2-g]chromene-9-sulfonic acid 4-[5-oxo-2-phenyl-oxazol-(4Z)-ylidenemethyl]-phenyl ester 
• 96944-54-6 C₁₉H₁₆N₄O₈S₂ 

Relevant articles and documents

Biotransformation of imperatorin by Penicillium janthinellum. Anti-osteoporosis activities of its metabolites

Imperatorin (IMP) is a major constituent of many herbal medicines and possesses anti-osteoporosis activity. The present research work aimed to study the biotransformation processes of IMP and evaluated the anti-osteoporosis activity of the transformed metabolites. Among 18 strains of filamentous fungi screened, Penicillium janthinellum AS 3.510 exhibited good capability to metabolise IMP to the new derivatives. Ten transformed products were isolated and purified, and their structures were identified accurately based on spectroscopic data. Eight metabolites (2-8 and 10) were novel and previously unreported. The major biotransformation reactions involved hydroxylation of the prenyloxy side-chain and the lactone ring-opening reaction of furocoumarin skeleton. In addition, anti-osteoporosis activities of all products (1-10) were evaluated using MC3T3-E1 cells. The results showed that products 5 and 8 had the best bioactivities in increasing MC3T3-E1 cell growth. These products could be used in future therapeutic regimens for treating osteoporosis.

An efficient synthesis of bergapten

An efficient synthesis of the linear furanocoumarin, bergapten, is reported. In order to avoid the formation of the angular furanocoumarin, we have adopted iodine as protecting group at the 8 position of the coumarin ring.

Isolation of two new coumarin glycosides from Notopterygium forbesii and evaluation of a Chinese crude drug, Qiang-Huo, the underground parts of N. incisum and N. forbesii, by high-performance liquid chromatography

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