CAS Number18642-23-4
SynonymsPsoralidin; 3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one; 3,9-Dihydroxy-2-prenylcoumestan; 3,9-Dihydroxy-2-(3-methyl-2-buten-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one; 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one; 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-6-one; 6-(3-Methylbut-2-enyl)coumestrol; 3,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one
Molecular FormulaC20H16O5
Molecular Weight336.338
Purity98%%
Density1.4±0.1 g/cm3
Boiling Point458.8±34.0 °C at 760 mmHg
Melting Point290-292°
Appearancewhite to beige
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 18642-23-4 |
| Catalog No. | 2A-1169415 |
| Chinese Name | 补骨脂定 |
| Synonyms | Psoralidin; 3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one; 3,9-Dihydroxy-2-prenylcoumestan; 3,9-Dihydroxy-2-(3-methyl-2-buten-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one; 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one; 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-6-one; 6-(3-Methylbut-2-enyl)coumestrol; 3,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromen-6-one |
| Molecular Formula | C20H16O5 |
| Molecular Weight | 336.338 |
| Purity | 98% |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 458.8±34.0 °C at 760 mmHg |
| Melting Point | 290-292° |
| Appearance | white to beige |
| Water Solubility | DMSO: soluble5mg/mL, clear (warmed) |
| Storage Condition | ?20°C |
| Application | Psoralidin is a natural furanocoumarin isolated from psoralen and has anti-cancer activity. |
| HTC | 2932999099 |
| PubChem ID | 12706 |
| SMILES | CC(C)=CCc1cc2c(cc1O)oc(=O)c1c3ccc(O)cc3oc21 |
| InChI | InChI=1S/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 |
| InChI Key | YABIJLLNNFURIJ-UHFFFAOYSA-N |
| Use of | Psoralidin, a natural furanocoumarin, is isolated from Psoralea corylifolia L. possessing anti-cancer properties.IC50 value:Target: Anticancer natural compoundin vitro: PSO dramatically decreased the cell viabilities in dose- and time-dependent manner. Autophagy inhibitor 3-MA blocked the production of LC3-II and reduced the cytotoxicity in response to PSO. Furthermore, PSO increased intracellular ROS level which was correlated to the elevation of LC3-II [1]. Psoralidin at 10 μM was able to induce the maximum reporter gene expression corresponding to that of E2-treated cells and such activation of the ERE-reporter gene by psoralidin was completely abolished by the cotreatment of a pure ER antagonist, implying that the biological activities of psoralidin are mediated by ER [2]. Psoralidin enhanced TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2 death receptor and depolarization of mitochondrial membrane potential [3]. Psoralidin inhibited the IR-induced COX-2 expression and PGE(2) production through regulation of PI3K/Akt and NF-κB pathway. Also, psoralidin blocked IR-induced LTB(4) production, and it was due to direct interaction of psoralidin and 5-lipoxygenase activating protein (FLAP) in 5-LOX pathway. IR-induced fibroblast migration was notably attenuated in the presence of psoralidin [4].in vivo: Moreover, in vivo results from mouse lung indicate that psoralidin suppresses IR-induced expression of pro-inflammatory cytokines (TNF-α, TGF-β, IL-6 and IL-1 α/β) and ICAM-1[4]. Properties Articles14 Name psoralidin Synonym More Synonyms Psoralidin Biological Activity Description Psoralidin, a natural furanocoumarin, is isolated from Psoralea corylifolia L. possessing anti-cancer properties.IC50 value:Target: Anticancer natural compoundin vitro: PSO dramatically decreased the cell viabilities in dose- and time-dependent manner. Autophagy inhibitor 3-MA blocked the production of LC3-II and reduced the cytotoxicity in response to PSO. Furthermore, PSO increased intracellular ROS level which was correlated to the elevation of LC3-II [1]. Psoralidin at 10 μM was able to induce the maximum reporter gene expression corresponding to that of E2-treated cells and such activation of the ERE-reporter gene by psoralidin was completely abolished by the cotreatment of a pure ER antagonist, implying that the biological activities of psoralidin are mediated by ER [2]. Psoralidin enhanced TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2 death receptor and depolarization of mitochondrial membrane potential [3]. Psoralidin inhibited the IR-induced COX-2 expression and PGE(2) production through regulation of PI3K/Akt and NF-κB pathway. Also, psoralidin blocked IR-induced LTB(4) production, and it was due to direct interaction of psoralidin and 5-lipoxygenase activating protein (FLAP) in 5-LOX pathway. IR-induced fibroblast migration was notably attenuated in the presence of psoralidin [4].in vivo: Moreover, in vivo results from mouse lung indicate that psoralidin suppresses IR-induced expression of pro-inflammatory cytokines (TNF-α, TGF-β, IL-6 and IL-1 α/β) and ICAM-1[4]. Related Catalog Signaling Pathways >> Stem Cell/Wnt >> Notch Natural Products >> Phenylpropanoids Research Areas >> Cancer References [2]. Liu X, et al. Psoralidin, a coumestan analogue, as a novel potent estrogen receptor signaling molecule isolated from Psoralea corylifolia. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1403-6. [3]. Bronikowska J, et al. The coumarin psoralidin enhances anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Molecules. 2012 May 29;17(6):6449-64. [4]. Yang HJ, et al. Psoralidin, a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation. Biochem Pharmacol. 2011 Sep 1;82(5):524-34. Chemical & Physical Properties Molecular Formula C20H16O5 Exact Mass 336.099762 PSA 83.81000 Appearance of Characters white to beige Index of Refraction 1.689 InChIKey YABIJLLNNFURIJ-UHFFFAOYSA-N Safety Information RIDADR NONH for all modes of transport HS Code 2932999099 Synthetic Route Total: 1 Page 2-Methylbut-2-ene CAS#:513-35-9 2-allyl-3,9-dih... CAS#:1134605-70-1 (E)-2-(but-2-en... CAS#:1134605-73-4 Psoralidin CAS#:18642-23-4 Literature: Journal of Organic Chemistry, , vol. 74, # 7 p. 2750 - 2754 Precursor & DownStream Precursor 2 CAS#:513-35-9 2-Methylbut-2-ene CAS#:1134605-70-1 2-allyl-3,9-dih... DownStream 0 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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