62442-57-3

Basic information

• Product Name: 3-CHLOROMETHYL-2,5,9-TRIMETHYL-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE
• Synonyms: 4'-CHLOROMETHYL-4,5',8-TRIMETHYLPSORALEN;3-CHLOROMETHYL-2,5,9-TRIMETHYL-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE;3-(Chloromethyl)-2,5,9-trimethyl-7H-furo[3,2-G]chromen-7-one;Aids014488;Aids-014488;Nsc291833;Nsc671202
• CAS NO: 62442-57-3
• Molecular Formula: C₁₅H₁₃ClO₃
• Molecular Weight: 276.71
• Mol File: 62442-57-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 449.7°C at 760 mmHg
• Flash Point: 225.8°C
• Appearance: /
• Density: 1.303g/cm³
• Vapor Pressure: 2.79E-08mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 3-CHLOROMETHYL-2,5,9-TRIMETHYL-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROMETHYL-2,5,9-TRIMETHYL-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE(62442-57-3)
• EPA Substance Registry System: 3-CHLOROMETHYL-2,5,9-TRIMETHYL-7H-FURO[3,2-G][1]BENZOPYRAN-7-ONE(62442-57-3)

Safety Data

• Hazardous Substances Data: 62442-57-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H13ClO3/c1-7-4-13(17)19-14-8(2)15-11(5-10(7)14)12(6-16)9(3)18-15/h4-5H,6H2,1-3H3

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 3902-71-4 trioxsalen 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 64358-50-5 4’-aminomethyl-4,5’,8-trimethylpsoralen 
• 62442-60-8 4'-methoxymethyl-4,5',8-trimethyl psoralen 
• 62442-59-5 4'-hydroxymethyl-4,5',8-trimethylpsoralen 
• 62442-58-4 4'-N-Phthalimidomethyl-4,5',8-trimethylpsoralen 
• 78318-60-2 4-(<β-hydroxyethoxy>methyl)-4,5',8-trimethylpsoralen 
• 1018958-00-3 6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[(4,5',8-trimethyl)psoralen-4'-ylmethyl]adenosine 
• 1018957-99-7 6-N-benzoyl-2'-O-[(4,5',8-trimethyl)psoralen-4'-ylmethyl]adenosine 
• 1018957-98-6 6-N,N-dibenzoyl-2'-O-[(4,5',8-trimethyl)psoralen-4'-ylmethyl]-3',5'-O-bis(trimethylsilyl)adenosine 
• 152235-91-1 4'-methylen-(3,3'-diamino-N-methyldipropylamine)-4,5',8-trimethylpsoralen 

Relevant articles and documents

Binding of lectins to DNA micro-assemblies: Modification of nucleo-cages with lactose-conjugated psoralen

Spherical DNA micro-assemblies appended with lactose units (Lactose-nucleo-cages, Lac-NC) are newly developed. DNA spherical assemblies self-assembled from suitably designed three oligodeoxyribonucleotides (ODNs) 1-3 were cross-linked by lactose-conjugated psoralen derivative 4. Confocal laser scanning fluorescence microscopy (CLSM) observation of Lac-NC shows that rhodamine labeled peanut lectin (Rho-PNA: a galactose-specific lectin) binds to lactose-modified nucleo-cages with higher affinity compared to that of unmodified nucleo-cages. Binding isotherm experiments indicated that the apparent affinity constant of Rho-PNA to Lac-NC was in the order of 105 M-1.

Design and Application of Mini-libraries of miRNA Probes for an Efficient and Versatile miRNA-mRNA Cross-linking

MicroRNAs constitute a class of endogenous, non-coding RNAs that influence various processes within the cell. By base-pairing to partially-complementary sites located in the 3’ untranslated region of target messenger RNAs, microRNAs participate in post-transcriptional regulation of the majority of human protein-coding genes. Their dysregulation has been related to many pathological processes and diseases. Thus, an in-depth understanding of the microRNA mechanisms of action is crucial. Here, we present a new concept of probe design to achieve an efficient and sequence-independent miRNA-mRNA cross-linking. The new strategy is based on the utilization of a controlled mixture of probes for a chosen miRNA, in which a trioxsalen moiety is introduced at the N4-position of a selected cytidine through short oligoethylene glycol-based linkers. In vitro photo-cross-linking experiments with mini-libraries of probes for microRNAs of interest showed variable cross-linking efficiencies, demonstrating a general applicability of the presented approach.

Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: Synthesis and photoreactivity

A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8- Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.