8-Methoxypsoralen Chemical Properties
- Melting point:
- 148-150 °C(lit.)
- Boiling point:
- 276.6°C (rough estimate)
- 1.1344 (rough estimate)
- refractive index
- 1.4270 (estimate)
- storage temp.
- -20°C Freezer, Under Inert Atmosphere
- H2O: slightly soluble
- Needle-Like Crystals or Powder
- white to yellow
- Water Solubility
- PRACTICALLY INSOLUBLE
- CAS DataBase Reference
- 298-81-7(CAS DataBase Reference)
- NIST Chemistry Reference
- 1 (Vol. 24, Sup 7, 100A) 2012
- EPA Substance Registry System
- Methoxsalen (298-81-7)
8-Methoxypsoralen Usage And Synthesis
8-methoxypsoralen (also known as methoxsalen) is a naturally occurring furocoumarin compound existing in several species of plants such as Psoralea corylifolia. It is a photoactive substance that can form DNA adducts upon UVA irradiation. It is a drug used for the treatment of psoriasis, eczema, vitiligo, and some kinds of cutaneous lymphomas associated with the exposure of skin to the UVA or light from lamps or sunlight. Its mechanism of action is through inhibiting the synthesis of the deoxyribonucleic acid (DNA). After the activation, it can preferentially bind to the guanine and cytosine molecules of DNA, further leading to the cross-linking of DNA, thus inhibiting the DNA synthesis. It can further inhibit the RNA and protein synthesis at high concentration. It is extracted from Ammi majus.
White to cream-colored, crystalline solid; odorless. Slightly soluble in alcohol; practically insoluble in water. Combustible.
antipsoriatic, pigmentation agent
Naturally occurring analog of Psoralen (P839800). Use in treatment of psoriasis and mycosis fungoides.
For the treatment of psoriasis and vitiligo
A potent suicide inhibitor of cytochrome P-450.
Naturally occurring analog of psoralen. Use in treatment of psoriasis and mycosis fungoides
Methoxsalen has effects similar to those of trioxsalen. Methoxsalen is superior to trioxsalen in producing erythema and tanning and is the drug used in PUVA therapy. Methoxsalen is also available as a 1% lotion.
ChEBI: A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.
It has been found that the compound 8-geranoxy psoralen is present in citrus
oils, particularly lemon and lime oils. This compound can be isolated from the
oil by a process which involves primarily absorption on an adsorbent material
followed by elution with a suitable solvent.
(A) Cleavage of 8-Geranoxypsoralen: 275 mg of 8-geranoxypsoralen was dissolved with mechanical stirring in 4 ml glacial acetic acid. After 10 minutes,one drop of concentrated sulfuric acid was added to the solution. In 4 minutes thereafter a light tan precipitate began to form. Stirring was continued for 35 minutes and the reaction mixture was refrigerated for one hour and 20 minutes. The precipitate was then removed by suction filtration and washed on the filter with glacial acetic acid followed by ice-cold ethyl ether. The product, 8-hydroxypsoralen, weighed 115 mg, that is, 74% of theory.
(B) Methylation of 8-Hydroxypsoralen: 115 mg of 8-hydroxypsoralen was dissolved in 10 ml absolute methanol, an excess of diazomethane dissolved in ether was added and the mixture allowed to stand at room temperature with occasional stirring for 3 hours. The next day the reaction mixture was reduced in volume to 3 ml by evaporation on the steam bath and the concentrate was held in a refrigerator overnight. The next day, fine needles (80 mg) of 8- methoxypsoralen were filtered from the solution. The compound had a MP of 145 to 146°C and was obtained in a yield of 65% of theory.
There is also a wholly synthetic route to Methoxsalen as outlined by Kleeman and Engel.
8-Mop (Valeant); Oxsoralen (Valeant); Uvadex (Therakos).
Dermal pigmentation enhancer
Odorless white to cream-colored crystalline solid. Bitter taste followed by tingling sensation.
Air & Water Reactions
Sensitive to light and air. Insoluble in water.
8-Methoxypsoralen is incompatible with strong oxidizing agents.
Flash point data for 8-Methoxypsoralen are not available; however, 8-Methoxypsoralen is probably combustible.
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.
Confirmed carcinogen. Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. A drug used to treat slun diseases.
Purify xanthotoxin by recrystallisation from *C6H6/pet ether (b 60-80o) to give silky needles, or from EtOH/Et2O to give rhombic prisms or from hot H2O to give needles. It is soluble in aqueous alkali due to ring opening of the cyclic lactone but recyclises upon acidification. It has UV max in EtOH at 219, 249 and 300nm (log 4.32, 4.35 and 4.06) and 1H NMR in CDCl3 with at 7.76 (d, 1H, J 10 Hz), 7.71 (d, 1H, J 2.5 Hz), 7.38 (s, 1H), 6.84 (d, 1H, J 2.5 Hz), 6.39 (d, 1H, J 10 Hz) and 4.28 (s, 3H)ppm. [Nore & Honkanen J Heterocycl Chem 17 985 1980.] It is a DNA intercalator, is used in the treatment of dermal diseases, and is a human carcinogen [Tessman et al. Biochemistry 24 1669 1985.] [Beilstein 19 I 711, 19/6 V 15.]
- Prickly ash extract
- AKOS 233-41
- AKOS 214-67
- POLY(ETHYLENE GLYCOL) METHYL ETHER ACRYLATE
- Methoxyacetic acid
- m-Anisyl alcohol
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