Bergapten Property

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 

Solid

color 

White to Pale Yellow

Merck 

14,1157

BRN 

19560

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.

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

5-Methoxypsoralen (484-20-8)

Safety

Hazard Codes 

Xi,T

Risk Statements 

43-45

Safety Statements 

36/37-45-53

WGK Germany 

2

RTECS 

LV1300000

F 

8-10

HS Code 

29322090

Hazardous Substances Data

484-20-8(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H341Suspected of causing genetic defects

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

Bergapten Chemical Properties,Usage,Production

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

Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic

Uses

Has been used to promote tanning in suntan preparations.

Uses

antipsoriatic, antiinflammatory

Uses

Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.

Uses

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.

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.

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.]