Bergapten
- Product Name
- Bergapten
- CAS No.
- 484-20-8
- Chemical Name
- Bergapten
- Synonyms
- 5-MOP;4-MOP;Geralen;MAJUDIN;HERACLIN;NSC 95437;BERGAPTEN;Bergaptan;Psoraderm;Bergaptene
- 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)
- NIST Chemistry Reference
- 7H-furo[3,2-g][1]benzopyran-7-one, 4-methoxy-(484-20-8)
- IARC
- 2A (Vol. 40, Sup 7) 1987
- 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.
N-Bromosuccinimide Price
- Product number
- PHL89865
- Product name
- 5-Methoxypsoralen
- Purity
- phyproof? Reference Substance
- Packaging
- 50MG
- Price
- $358
- Updated
- 2024/03/01
- Product number
- 275727
- Product name
- 5-Methoxypsoralen
- Purity
- 99%
- Packaging
- 250mg
- Price
- $126
- Updated
- 2024/03/01
- Product number
- 275727
- Product name
- 5-Methoxypsoralen
- Purity
- 99%
- Packaging
- 1g
- Price
- $402
- Updated
- 2024/03/01
- Product number
- B2840
- Product name
- Bergapten
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $203
- Updated
- 2024/03/01
- Product number
- B2840
- Product name
- Bergapten
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $731
- Updated
- 2024/03/01
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.]
Bergapten Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Bergapten manufacturers
- Product
- Bergapten 484-20-8
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-11-01
- Product
- Bergapten 484-20-8
- Price
- US $25.00-10.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 10 tons
- Release date
- 2023-11-23
- Product
- Bergapten 484-20-8
- Price
- US $0.00/G
- Min. Order
- 1G
- Purity
- 99%
- Supply Ability
- 100kg/Quater
- Release date
- 2023-09-11