| Identification | More | [Name]
Bergapten | [CAS]
484-20-8 | [Synonyms]
4-METHOXYFURO[3.2-G]BENZOPYRAN-7-ONE
4-METHOXYFURO[3,2-G]BENZOPYRANE-7-ONE
4-MOP
5-METHOXYPSORALEN
5-MOP
7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE,4-METHOXY
AKOS 201-13
BERGAPTEN
HERACLIN
MAJUDIN
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
Bergaptan
Bergaptene | [EINECS(EC#)]
207-604-5 | [Molecular Formula]
C12H8O4 | [MDL Number]
MFCD00010272 | [Molecular Weight]
216.19 | [MOL File]
484-20-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [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
| [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
White to Pale Yellow | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive. | [Usage]
Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic | [Merck ]
1157 | [BRN ]
19560 | [Contact allergens]
This 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. | [LogP]
2.035 (est) | [CAS DataBase Reference]
484-20-8(CAS DataBase Reference) | [IARC]
2A (Vol. 40, Sup 7) 1987 | [NIST Chemistry Reference]
7H-furo[3,2-g][1]benzopyran-7-one, 4-methoxy-(484-20-8) | [EPA Substance Registry System]
484-20-8(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
A psoralen phytotoxic citrus essential oil found in bergamont | [Uses]
antipsoriatic, antiinflammatory | [Uses]
Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic. | [Uses]
Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic | [Definition]
ChEBI: A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5. | [Uses]
Has been used to promote tanning in suntan preparations. | [General Description]
Grayish-white microcrystalline powder or yellow fluffy solid. | [Reactivity Profile]
5-METHOXYPSORALEN(484-20-8) may be sensitive to exposure to light. A related chemical is incompatible with strong oxidizers. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available; however, 5-METHOXYPSORALEN is probably combustible. | [Description]
Bergapten exists in roots, stems, and leaves of a variety of Rutaceae, Umbelliferae, and leguminous plants such as ephedra, fennel, and vetch. | [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. | [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.] |
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