66-97-7 Usage
Description
Psoralen is a kind of naturally occurring furocoumarin. It is naturally occurred in the seeds of Psoralea corylifolia as well as in the common fig, celery, parsley, West Indian Satinwood and all citrus fruits. It is capable of binding to DNA via single- and double-strand cross-linking upon photoactivation with UV radiation. It can intercalate with DNA, blocking its synthesis and cell division. For this reason, it is an important mutagen and can be used in related molecular biology studies. It also exhibits anti- proliferative, anti-allergenic and anti-histamine functions. It can also be used in PUVA treatment for skin diseases such as psoriasis, eczema and vitiligo. It is also effective tanning activator in sunscreens. Some of its derivatives, e.g. amino-psoralen, amotosalen HCl, can even inactivate pathogens in blood products.
References
https://en.wikipedia.org/wiki/Psoralen
https://pubchem.ncbi.nlm.nih.gov/compound/Psoralen#section=Top
Chemical Properties
Crystalline Solid
Uses
Different sources of media describe the Uses of 66-97-7 differently. You can refer to the following data:
1. Use as photochemical probe in biological systems
2. Psoralens are phytoalexins; they are used by plants in a defensive response to attacks by fungi and insects. They have also shown photosensitizing and phototoxic effects in animals and humans and have
been used in photochemotherapy for management of vitiligo, psoriasis, and mycosis fungoides. Used as photochemical probe in biological systems.
3. As photochemical probe in biological systems: P.-S. Song, C.-N. Ou, Ann. N.Y. Acad. Sci. 346, 355 (1980).
Definition
ChEBI: The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.
Synthesis Reference(s)
Journal of the American Chemical Society, 106, p. 6735, 1984 DOI: 10.1021/ja00334a044Synthetic Communications, 37, p. 63, 2007 DOI: 10.1080/00397910600978093
Biochem/physiol Actions
Psoralen belongs to the linear type furanocoumarins. It intercalates and induces interstrand cross-links in DNA. On UV exposure psoralen is excited leading to irreversible intercalation with DNA by covalent bond formation. This property of psoralen ultraviolet A light (PUVA) is exploited in treating skin diseases and cutaneous T-cell lymphoma. However, usage psoralen also leads to hepatotoxicity and cytotoxicity by the generation of psoralen photoproducts (POPs). It may be useful in treating osteoporosis
Check Digit Verification of cas no
The CAS Registry Mumber 66-97-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 6 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 66-97:
(4*6)+(3*6)+(2*9)+(1*7)=67
67 % 10 = 7
So 66-97-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H
66-97-7Relevant articles and documents
Ph-dependent photoinduced interconversion of furocoumaric and furocoumarinic acids
Boldyrev, Ivan A.,Malakhov, Mikhail V.,Maslov, Mikhail A.,Matrosov, Anton A.,Negrebetsky, Vadim V.,Nichugovskiy, Artemiy I.,Skarga, Vladislav V.
, (2021)
Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being (Z/E)-isomers relative to each other were obtained in two stages starting from psoralen: the alkaline solvolysis of psoralen led to furocoumaric acid, which was further Z → E photoisomerized (365 nm) to furocoumarinic acid. The kinetics of Z → E photoisomerization was monitored by HPLC and UV-vis spectrophotometry. Photophysical characteristics in the aqueous phase for both acids, as well as the reversibility of (Z/E) photoisomerization process, were also assessed. Furocoumarinic acid was found to be visibly fluorescent at pH 2.0–12.0, with the maxima of fluorescence emission spectra being pH-dependent. The reverse E → Z photoisomerization predicted by quantum chemistry calculations as energetically favorable for the monoanionic form of furocoumarinic acid was proved in the experiment while being complicated by pyrone ring closure back to psoralen in acidic and neutral conditions. The preparative synthesis of furocoumarinic acid outlined in this work is particularly valuable in view of a wide range of pharmacological effects previously predicted for this compound.
A new efficient method for the total synthesis of linear furocoumarins
Zhang, Bang-Le,Wang, Fang-Dao,Yue, Jian-Min
, p. 567 - 570 (2007/10/03)
A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann reaction. This strategy has also been applied to the preparation of four additional benzofuran derivatives. Georg Thieme Verlag Stuttgart.
A convenient synthesis of psoralens
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Viola, Giampietro,Vedaldi, Daniela,Dall'Acqua, Francesco
, p. 4859 - 4863 (2007/10/03)
An efficient synthesis (yields >70%) of linear 7H-furo[3,2-g]chromen-7-one derivatives (psoralens or furocoumarins) has been carried out starting from ring-substituted 2-(coumarin-7-yl)oxyaldehydes; moreover, the phototoxicity of these compounds has been tested on a cultured cell line of murine fibroblast.
