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Bergapten

CAS No.484-20-8
Chemical Name:Bergapten
CBNumber:CB7125968
Molecular Formula:C12H8O4
Formula Weight:216.19
MOL File:484-20-8.mol

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)
FDA UNII 4FVK84C92X
NIST Chemistry Reference 7H-furo[3,2-g][1]benzopyran-7-one, 4-methoxy-(484-20-8)
IARC 2A (Vol. 40, Sup 7) 1987
ATC code D05BA03
EPA Substance Registry System 5-Methoxypsoralen (484-20-8)
UNSPSC Code 85151701
NACRES NA.24

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 wordWarning
Hazard statements H317-H341-H351
Precautionary statements P202-P261-P272-P280-P302+P352-P308+P313

Bergapten Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: 275727
Product name : 5-Methoxypsoralen
Purity: 99%
Packaging: 250MG
Price: ₹7480.08
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 69664
Product name : Bergapten
Purity: analytical standard
Packaging: 25MG
Price: ₹12816.8
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 275727
Product name : 5-Methoxypsoralen
Purity: 99%
Packaging: 1G
Price: ₹23750.05
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: B2840
Product name : Bergapten
Purity: min. 98.0 %
Packaging: 1G
Price: ₹6600
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: B2840
Product name : Bergapten
Purity: min. 98.0 %
Packaging: 5G
Price: ₹9900
Updated: 2022/05/26
Buy: Buy

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 Has been used to promote tanning in suntan preparations.
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.
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.]