Psoralen

Base Information

• Chemical Name: Psoralen
• CAS No.: 66-97-7
• Molecular Formula: C11H6O3
• Molecular Weight: 186.167
• Hs Code.: 29339900
• European Community (EC) Number: 200-639-7
• NSC Number: 404562
• UNII: KTZ7ZCN2EX
• DSSTox Substance ID: DTXSID00216205
• Nikkaji Number: J2.363I
• Wikipedia: Psoralen
• Wikidata: Q417788
• NCI Thesaurus Code: C2586
• Pharos Ligand ID: 6M1KJ6791M4T
• Metabolomics Workbench ID: 46464
• ChEMBL ID: CHEMBL164660
• Mol file: 66-97-7.mol

Synonyms:Ficusin;Psoralen;Psoralene

Chemical Property of Psoralen

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Melting Point: 160-162 °C
• Refractive Index: 1.667
• Boiling Point: 362.6 °C at 760 mmHg
• Flash Point: 173.1 °C
• Density: 1.389 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: 65.16mg/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 186.031694049
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

more than 96%,98% ^*data from raw suppliers

Psoralen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Dermatologic Agents, Psoriasis Agents
• Canonical SMILES: C1=CC(=O)OC2=CC3=C(C=CO3)C=C21
• Recent ClinicalTrials: Chemotherapy, Radiation Therapy, and Peripheral Stem Cell Transplantation in Treating Patients With Hematologic Cancer
• Recent NIPH Clinical Trials: Efficacy and safety of bexarotene or bexarotene plus phototherapy in CTCL
• 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.
• Uses: Use as photochemical probe in biological systems 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. As photochemical probe in biological systems: P.-S. Song, C.-N. Ou, Ann. N.Y. Acad. Sci. 346, 355 (1980).

Technology Process of Psoralen

There total 38 articles about Psoralen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(2S,3R)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one (87725-60-8) → psoralen (66-97-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 1.33333h;

DOI:10.1021/jo047974k

Reference yield: 100.0%

(2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one (849144-95-2) → psoralen (66-97-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 0.666667h;

DOI:10.1021/jo047974k

Reference yield: 76.0%

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde (16851-02-8) → psoralen (66-97-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 4h; Heating;

DOI:10.1080/00397910600978093

upstream raw materials:

(E)-3-(6-hydroxybenzofuran-5-yl)acrylic acid

4',5'-dihydropsolaren

7-demethylsuberosin

7-oxo-2,3-dihydro-7H-furo[3,2-g]chromene-6-carboxylic acid

Downstream raw materials:

6-hydroxy-5-benzofurancarboxaldehyde

6-(1,2-diphenyl-ethyl)-7-hydroxy-chromen-2-one

Refernces

• 1、 Zhang, Bang-Le,Wang, Fang-Dao,Yue, Jian-Min. "Concise and efficient synthesis of linear furocoumarins: Psoralen and 4-methylpsoralen". . p. 63 - 70. Retrieved 2007/10/03.
• 2、 Zou, Yefen,Lobera, Mercedes,Snider, Barry B.. "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". . p. 1761 - 1770. Retrieved 2007/10/03.