메톡살렌 C화학적 특성, 용도, 생산
개요
8-Methoxypsoralen (8-MOP) and other psoralens are naturally
found in plants, including common fruit and vegetable crops.
화학적 성질
White to cream-colored, crystalline
solid; odorless. Slightly soluble in alcohol; practically insoluble in water. Combustible.
용도
8-Methoxypsoralen, is used in Photochemotherapy (methoxsalen with long wave ultraviolet radiation) is indicated for the repigmentation of idiopathic vitiligo. It is also used in Photopheresis (methoxsalen with long wave ultraviolet radiation of white blood cells) is indicated for use with the UVAR* System in the palliative treatment of the skin manifestations of cutaneous T-cell lymphoma.
Indications
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.
정의
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.
일반 설명
Odorless white to cream-colored crystalline solid. Bitter taste followed by tingling sensation.
공기와 물의 반응
Sensitive to light and air. Insoluble in water.
반응 프로필
8-Methoxypsoralen is incompatible with strong oxidizing agents.
화재위험
Flash point data for 8-Methoxypsoralen are not available; however, 8-Methoxypsoralen is probably combustible.
색상 색인 번호
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.
Safety Profile
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.
환경귀착
The industrial use of 8-MOP results in its release into the
environment through multiple pathways, and its existence as
a natural substance in plants further expands exposure to the
environment. Airborne 8-MOP will exist in the vapor and
particulate phases, and will be degraded in air by reaction with
photochemically produced hydroxyl radicals, with an estimated
half-life of approximately 1.2 h, it may also be subject to
direct photolysis by sunlight. Particulate 8-MOP will be
removed from the atmosphere by wet or dry deposition. If
released into the soil, it is expected to have high mobility and is
not expected to volatilize. 8-MOP does not biodegrade. In
aqueous environments, 8-MOP is not expected to hydrolyze, it
will, however, adsorb to suspended solids and sediment. Due
to 8-MOP’Ks resistance to degradation by many routes, it is
expected to remain in the environment for a prolonged period,
and as such will also be subject to long-range transport. 8-MOP
has an estimated bioconcentration factor (BCF) of 9, meaning
that bioconcentration and bioaccumulation are low in aquatic
organisms.
Purification Methods
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.]
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