66-97-7

Basic information

• Product Name: Psoralen
• Synonyms: PSORALEN;7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE;7h-furo[3,2-g]benzopyran-7-one;FURO[3,2-G]BENZOPYRAN-7-ONE;FURO[3,2-G]COUMARIN;FICUSIN;2-Propenoic acid, 3-(6-hydroxy-5-benzofuranyl)-, delta-lactone;2-Propenoicacid,3-(6-hydroxy-5-benzofuranyl)-,δ-lactone
• CAS NO: 66-97-7
• Molecular Formula: C₁₁H₆O₃
• Molecular Weight: 186.16
• EINECS: 200-639-7
• Product Categories: Coumarins;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 66-97-7.mol

Chemical Properties

• Melting Point: 160-162 °C
• Boiling Point: 280.64°C (rough estimate)
• Flash Point: 173.1 °C
• Appearance: Crystalline solid
• Density: 1.2477 (rough estimate)
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Refractive Index: 1.6310 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: 65.16mg/L(25 oC)
• Merck: 14,7928
• BRN: 152784
• CAS DataBase Reference: Psoralen(CAS DataBase Reference)
• NIST Chemistry Reference: Psoralen(66-97-7)
• EPA Substance Registry System: Psoralen(66-97-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: LV0944000
• F: 8-10
• Hazardous Substances Data: 66-97-7(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology Research:
Psoralen is used as a photochemical probe in biological systems for studying DNA interactions and mutations, as well as for understanding the mechanisms of DNA repair and cell division.
Used in Photochemotherapy:
Psoralens, as phytoalexins, are used in photochemotherapy for the management of skin conditions such as vitiligo, psoriasis, and mycosis fungoides. They exhibit photosensitizing and phototoxic effects, which contribute to the treatment's effectiveness.
Used in Skin Treatments:
Psoralen is used in PUVA treatment for various skin diseases, including psoriasis, eczema, and vitiligo, due to its anti-proliferative, anti-allergenic, and anti-histamine functions.
Used in Sunscreen Formulations:
As an effective tanning activator, Psoralen is used in sunscreens to provide protection against harmful UV radiation.
Used in Blood Product Pathogen Inactivation:
Some derivatives of Psoralen, such as amino-psoralen and amotosalen HCl, are used to inactivate pathogens in blood products, ensuring the safety of transfusions and other blood-related medical procedures.
Used as a Photochemical Probe in Biological Systems (Reference):
Psoralen's use as a photochemical probe in biological systems has been documented in various studies, such as the work by P.-S. Song and C.-N. Ou in the Annals of the New York Academy of Sciences, volume 346, page 355, published in 1980.

References

https://en.wikipedia.org/wiki/Psoralen https://pubchem.ncbi.nlm.nih.gov/compound/Psoralen#section=Top

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

InChI:InChI=1/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H

Upstream product

• 21422-04-8 7-demethylsuberosin 
• 849144-95-2 (2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one 
• 15085-71-9 Micromelumin 
• 37570-37-9 6-allyl-7-hydroxy-2H-1-benzopyran-2-one 
• 6544-89-4 3,4-dihydropsoralen 
• 7535-48-0 4',5'-dihydropsolaren 
• 495-68-1 (E)-3-(6-hydroxybenzofuran-5-yl)acrylic acid 
• 52085-14-0 4-benzoxy-salicylaldehyde 
• 412300-65-3 4-benzyloxy-2-[ethyloxycarbonylmethoxy]benzaldehyde 
• 875815-32-0 (5-benzyloxy-2-formyl-phenoxy)-acetic acid 
• 320350-81-0 6-benzyloxy-benzofuran 
• 24416-63-5 6-hydroxy-2,3-dihydro-1-benzofuran-5-carboxaldehyde 
• 23681-89-2 2,3-dihydro-6-hydroxybenzofuran 
• 13196-11-7 6-hydroxybenzofuran 

Downstream Products

• 31231-45-5 6-(1,2-diphenyl-ethyl)-7-hydroxy-chromen-2-one 
• 20073-22-7 6-hydroxy-5-benzofurancarboxaldehyde 

Relevant articles and documents

Ph-dependent photoinduced interconversion of furocoumaric and furocoumarinic acids

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.

Concise and efficient synthesis of linear furocoumarins: Psoralen and 4-methylpsoralen

A method for the rapid synthesis of psoralen and 4-methylpsoralen has been developed. The key intermediates, coumarinyloxyaldehydes, were obtained in only two steps from the easily available starting materials, 7-hydroxycoumarin derivatives, by an oxidative procedure. By using Swern oxidation, psoralen and 4-methylpsoralen were finally produced in the overall yields of 71% and 67%, respectively. Copyright Taylor & Francis Group, LLC.

A new efficient method for the total synthesis of linear furocoumarins

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.

Synthesis of 2,3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, xanthoarnol, and avicenol A. Biomimetic syntheses of angelicin and psoralen

(Chemical Equation Presented) We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure α,β-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.

Process for the sterilization of biological compositions and the product thereby

The present invention concerns the product produced by inactivating extracellular or intracellular pathogenic virus in a biological composition without incurring substantial disruption or inactivation of cells and without significant loss of labile proteins or other valuable biological components also contained therein, the inactivation process comprising subjecting said composition to a virucidally effective amount of irradiation in the presence of (a) a mixture of a compound that quenches type I photodynamic reactions and a compound that quenches type II photodynamic reactions or (b) a bifunctional compound that is capable of quenching both type I and type II reactions, to thereby inactivate said virus while retaining functionality of said composition. The composition is advantageously subjected to the irradiation and the mixture of compounds or bifunctional compound in the presence of an irradiation sensitizer. Moreover, the process can be advantageously combined with a different virucidal method to enhance virus inactivation.

A convenient synthesis of psoralens

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.

Coumarins from Ferulago capillaris and F. brachyloba

Four new coumarins, (+)-senecioylprangol, (-)-3'-senecioyloxymarmesin, (+)-3'-hydroxyprantschimgin and (+)-2''-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd.

Process for the sterilization of biological compositions using UVA1 irradiation

An improvement in a process for inactivating extracellular and intracellular viruses in a platelet containing composition is presented. The improvement in the process comprises adding a sensitizer to the platelet containing composition and irradiating the composition containing the sensitizer with UVA1 in the absence of UVA2 for a period of time sufficient to inactivate the viruses while retaining the functionality of the platelet containing composition. A quencher or mixture of quenchers of type I and type II photodynamic reactions may be advantageously added to the composition prior to irradiation.

Reduced and quaternized psoralens as photo-activated therapeutics

The invention features phototherapeutic compositions comprising Type 1, Type 2, or Type 3 psoralens and methods of using such compounds for treatment of proliferative diseases of skin, blood and bone marrow.

Treatment methods for lymes disease and associated debilitating conditions

A method is provided for treating human patients who have Lymes disease by using a psoralen compound, preferably administered in a dosage of 0.3 to 0.7 mg/kg, and activating same either in vitro or in vivo using electromagnetic radiation of a prescribed activating wavelength. The activation of the psoralen compound in the presence of a blood fraction from a patient suffering from Lymes disease produces a composition which will stimulate an effective immune response to the Lymes disease on the part of the patient.