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Bergapten

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Bergapten Basic information

Product Name:
Bergapten
Synonyms:
  • 4-Methoxyfuro[3,2-g]benzopyrane-7-one, Bergapten
  • 5-Methoxyfurocoumarin
  • 5-Methoxypsoralen,4-Methoxyfuro[3,2-g]benzopyrane-7-one, Bergapten
  • 2-g)(1)benzopyran-7-one,4-methoxy-7h-furo(
  • 4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one
  • 4-methoxy-7H-furo[3,2-g][1]benzopyran-7-one
  • 4-Methoxy-7H-furo[3,2-g]chromen-7-one
  • BERGAPTEN WITH HPLC
CAS:
484-20-8
MF:
C12H8O4
MW:
216.19
EINECS:
207-604-5
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Inhibitors
  • PSORADERM-5
  • Aromatics
  • Heterocycles
  • Metabolites & Impurities
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Coumarins
Mol File:
484-20-8.mol
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Bergapten Chemical Properties

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 Information

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)

MSDS

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Bergapten Usage And Synthesis

Chemical Properties

Crystalline Solid

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

Uses

Has been used to promote tanning in suntan preparations.

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.

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.]

BergaptenSupplier

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