18642-23-4

Basic information

• Product Name: psoralidin
• Synonyms: 3,9-Dihydroxy-2-prenylcoumestan;Psoralidin, >=99%;psoralidin;3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one;Psorslidin
• CAS NO: 18642-23-4
• Molecular Formula: C₂₀H₁₆O₅
• Molecular Weight: 336.338
• Mol File: 18642-23-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 290-292°
• Boiling Point: 458.8°Cat760mmHg
• Flash Point: 231.3°C
• Appearance: white to beige/
• Density: 1.383g/cm³
• Vapor Pressure: 4.89E-09mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble5mg/mL, clear (warmed)
• PKA: 8.70±0.20(Predicted)
• CAS DataBase Reference: psoralidin(CAS DataBase Reference)
• NIST Chemistry Reference: psoralidin(18642-23-4)
• EPA Substance Registry System: psoralidin(18642-23-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 18642-23-4(Hazardous Substances Data)

Usage

Description

Psoralidin is a furanocoumarin isolated from the seeds of P. corylifolia, a medicinal plant found in southeastern Asia, that has been shown to induce cytotoxicity against various cancer cells. Through TNF-related apoptosis-inducing ligand-mediated events, psoralidin at 50 μM can induce the death of HeLa cancer cells. It also can induce apoptosis of androgen-dependent (LNCaP, C4-2B) and androgen-independent (DU-145, PC-3) prostate cancer cells and inhibit the growth of PC-3 xenograft tumors in nude mice.

Uses

Psoralidin is an antibacterial and antioxidant reagent.

Definition

ChEBI: A member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively.

references

[1] yang h j, youn h s, seong k m, et al. psoralidin, a dual inhibitor of cox-2 and 5-lox, regulates ionizing radiation (ir)-induced pulmonary inflammation[j]. biochemical pharmacology, 2011, 82(5): 524-534.[2] chiou w f, don m j, liao j f, et al. psoralidin inhibits lps-induced inos expression via repressing syk-mediated activation of pi3k-ikk-iκb signaling pathways[j]. european journal of pharmacology, 2011, 650(1): 102-109.[3] bronikowska j, szliszka e, jaworska d, et al. the coumarin psoralidin enhances anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (trail)[j]. molecules, 2012, 17(6): 6449-6464.

InChI:InChI=1/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3

Upstream product

• 513-35-9 2-methyl-but-2-ene 
• 1134605-70-1 2-allyl-3,9-dihydroxy-benzo[4,5]furo[3,2-c]chromen-6-one 

Related news

Pharmaceutical NanotechnologyNanoencapsulation of psoralidin (cas 18642-23-4) via chitosan and Eudragit S100 for enhancement of oral bioavailability10/01/2019

Psoralidin (PL) has recently been attracting more attention as a new anticancer agent candidate. Nevertheless, peroral administration of PL is largely challenged by its insoluble nature and intestinal efflux. This article aimed to develop a nanoencapsulation formulation of PL using water-soluble...detailed

Synthesis of psoralidin (cas 18642-23-4) derivatives and their anticancer activity: first synthesis of Lespeflorin I109/27/2019

Synthetic scheme for the preparation of a number of different derivatives of anticancer natural product Psoralidin is described. A convergent synthetic approach is followed using simple starting materials like substituted phenyl acetic esters and benzoic acids. The developed synthetic route lead...detailed

Comparison of the in vitro metabolism of psoralidin (cas 18642-23-4) among different species and characterization of its inhibitory effect against UDP- glucuronosyltransferase (UGT) or cytochrome p450 (CYP450) enzymes09/26/2019

Psoralidin has shown a variety of biological and pharmacological activities such as anti-tumor anti-oxidant, anti-bacterial, anti-depressant and anti-inflammatory activities. Herein, we reported the metabolism of psoralidin among different species and its inhibitory effect against UGTs and CYP45...detailed

psoralidin (cas 18642-23-4) suppresses osteoclastogenesis in BMMs and attenuates LPS-mediated osteolysis by inhibiting inflammatory cytokines09/10/2019

Psoralidin is a metabolic product from the seed of psoraleacorylifolia, possessed anti-inflammatory and immunomodulatory effects. We speculated that psoralidin might impact osteoclastogenesis and bone loss. By using both in vitro and in vivo studies, we observed psoralidin strongly inhibited RAN...detailed

The higher osteoprotective activity of psoralidin (cas 18642-23-4) in vivo than coumestrol is attributed by its presence of an isopentenyl group and through activated PI3K/Akt axis09/09/2019

Prenylation of bioactive natural compounds has been postulated to be able to enhance the utilization rate and affinity of the compounds with cell membranes, thus promote their bioactivities. Coumestrol, isolated from Medicago sativa, has been known as a phytoestrogen which has bone health benefi...detailed

Original ArticleEffect and mechanism of psoralidin (cas 18642-23-4) on promoting osteogenesis and inhibiting adipogenesis09/08/2019

BackgroundPsoralidin (PL), a prenylated coumestrol, is isolated from Psoralea corylifolia L. (Fabaceae), which is frequently used for treatment of osteoporosis.detailed

ReviewMechanisms explaining the efficacy of psoralidin (cas 18642-23-4) in cancer and osteoporosis, a review09/07/2019

Psoralidin (PSO) is a natural phenolic coumarin that is extracted from the seeds of Psoralea corylifolia L. PSO possesses a variety of pharmacological activities, including anti-oxidative, antibacterial, anti-inflammatory, anti-depressive and estrogenic-like effects. Other studies have indicated...detailed

Relevant articles and documents

Total synthesis of psoralidin, an anticancer natural product

A base-catalyzed condensation of phenyl acetate with acid chloride, followed by intramolecular cyclization and microwave-assisted cross-metathesis reaction, leads to the first total synthesis of psoralidin, a natural product with a broad range of biological activities, in a highly convergent and regioselective manner.