Bergapten

Base Information

• Chemical Name: Bergapten
• CAS No.: 484-20-8
• Molecular Formula: C12H8O4
• Molecular Weight: 216.193
• Hs Code.: 29322090
• European Community (EC) Number: 207-604-5
• NSC Number: 755877,95437
• UN Number: 1759
• UNII: 4FVK84C92X
• DSSTox Substance ID: DTXSID1025560
• Nikkaji Number: J12.563F
• Wikipedia: Bergapten
• Wikidata: Q414779
• Pharos Ligand ID: 63T39ZPCUZCK
• Metabolomics Workbench ID: 44484
• ChEMBL ID: CHEMBL24171
• Mol file: 484-20-8.mol

Synonyms:5 Methoxy Psoralen;5 Methoxypsoralen;5-Methoxy Psoralen;5-methoxypsoralen;bergapten;Pentaderm

Chemical Property of Bergapten

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 5.2E-07mmHg at 25°C
• Melting Point: 190-193 °C(lit.)
• Refractive Index: 1.635
• Boiling Point: 412.4 °C at 760 mmHg
• Flash Point: 203.2 °C
• PSA: 52.58000
• Density: 1.368 g/cm³
• LogP: 2.54780
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 216.04225873
• Heavy Atom Count: 16
• Complexity: 325
• Transport DOT Label: Corrosive

Purity/Quality:

Bergapten ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 43-45
• Safety Statements: 36/37-45-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
• Recent ClinicalTrials: Comparison of UVA1 Phototherapy Versus Photochemotherapy for Patients With Severe Generalized Atopic Dermatitis
• Recent EU Clinical Trials: UVA 1 therapy versus 5-MOP UVA photochemotherapy for patients with severe generalized atopic dermatitis
• 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.
• Uses: Naturally occurring analog of psoralen and isomer of methoxsalen. Found in a wide variety of plants. Antipsoriatic Has been used to promote tanning in suntan preparations. antipsoriatic, antiinflammatory Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic. A psoralen phytotoxic citrus essential oil found in bergamont
• 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.

Technology Process of Bergapten

There total 16 articles about Bergapten which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

9-iodo-5-methoxyfurano[3,2-g]chromen-2-one (122850-55-9) → bergapten (484-20-8)

Guidance literature:

With formic acid; triethylamine; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 11h;

DOI:10.3987/COM-05-10451

Reference yield: 40.0%

5-methoxy-7-(2-oxoethoxy)coumarin → bergapten (484-20-8)

Guidance literature:

With sodium hydroxide; for 4h; Heating;

DOI:10.1055/s-2006-958420

Reference yield: 1.0%

imperatorin (482-44-0) → heraclenol (31575-93-6,118407-74-2,139079-42-8,26091-76-9,2817-09-6) + bergapten (484-20-8) + C16H20O7 (1428263-43-7) + C17H22O7 (1428263-44-8) + C16H18O6 (1428263-45-9) + C16H18O6 (1428263-47-1) + C17H20O6 (1428417-34-8) + C16H20O6 (1428263-46-0) + C16H18O6 (1428417-33-7) + 6,7-furano-5-isopentylcoumarin 8-O-β-D-glucoside

Guidance literature:

With Penicillium janthinellum AS; liquid potato medium; In acetone; at 27 ℃; for 120h; Microbiological reaction;

DOI:10.1016/j.foodchem.2012.11.138

upstream raw materials:

diazomethane

bergaptol

dimethyl sulfate

9-iodo-5-methoxyfurano[3,2-g]chromen-2-one

Downstream raw materials:

bergaptol

C₁₉H₁₂O₆

C₂₁H₁₄O₆

C₂₅H₂₂O₆

Refernces

• 1、 Roux, Delphine,Makki, Safwat,Bévalot, Fran?oise,Humbert, Philippe. "Efficient total synthesis of 5-methoxypsoralen". . p. 129 - 130. Retrieved 2008/03/13.
• 2、 -. "Treatment methods for lymes disease and associated debilitating conditions". . . Retrieved 2008/06/13.