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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
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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
form 
neat
Merck 
14,1157
BRN 
19560
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.
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)
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Safety

Hazard Codes 
Xi,T
Risk Statements 
43-45
Safety Statements 
36/37-45-53
WGK Germany 
2
RTECS 
LV1300000
8-10
HS Code 
29322090
Hazardous Substances Data
484-20-8(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H340May cause genetic defects

H350May cause cancer

Precautionary statements

P201Obtain special instructions before use.

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.

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

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
275727
Product name
5-Methoxypsoralen
Purity
99%
Packaging
250mg
Price
$103
Updated
2021/03/22
Sigma-Aldrich
Product number
275727
Product name
5-Methoxypsoralen
Purity
99%
Packaging
1g
Price
$328
Updated
2021/03/22
TCI Chemical
Product number
B2840
Product name
Bergapten
Purity
>98.0%(GC)
Packaging
1g
Price
$167
Updated
2021/03/22
TCI Chemical
Product number
B2840
Product name
Bergapten
Purity
>98.0%(GC)
Packaging
5g
Price
$603
Updated
2021/03/22
Cayman Chemical
Product number
26254
Product name
Bergapten
Packaging
10g
Price
$935
Updated
2021/03/22
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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.]

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Bergapten Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96500
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
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Energy Chemical
Tel
021-58432009-
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
43499
Advantage
61
Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
20007
Advantage
64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202- ; ;
Email
jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com
Country
China
ProdList
43255
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32358
Advantage
50
Chengdu XiYa Chemical Technology Co., Ltd.
Tel
;
Fax
0539-6365991
Email
sale@xiyashiji.com;3007716753@qq.com
Country
China
ProdList
10578
Advantage
57
BEST-REAGENT
Tel
400-1166-196;028-84555506- ;028-84555506-
Email
cdhxsj@163.com;1955352637@qq.com;cdhxsj@163.com
Country
China
ProdList
11718
Advantage
57
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View Lastest Price from Bergapten manufacturers

NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Bergapten 484-20-8 484-20-8
Price
US $42.00/mg
Min. Order
20mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-07-11
Dideu Industries Group Limited
Product
Bergapten 484-20-8
Price
US $1.10/g
Min. Order
1g
Purity
99.00%
Supply Ability
100 Tons Min
Release date
2021-10-29
Hebei Crovell Biotech Co Ltd
Product
Bergapten 484-20-8
Price
US $10.70/g/Bag
Min. Order
10g
Purity
99%
Supply Ability
10000kg
Release date
2021-07-20

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