25474-45-7

Basic information

• Product Name: 4-(1-hydroxypropyl)benzene-1,2-diol
• CAS NO: 25474-45-7
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.1898
• Mol File: 25474-45-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 350.9°C at 760 mmHg
• Flash Point: 176.6°C
• Density: 1.256g/cm³
• Vapor Pressure: 1.58E-05mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 4-(1-hydroxypropyl)benzene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-hydroxypropyl)benzene-1,2-diol(25474-45-7)
• EPA Substance Registry System: 4-(1-hydroxypropyl)benzene-1,2-diol(25474-45-7)

Safety Data

• Hazardous Substances Data: 25474-45-7(Hazardous Substances Data)

Upstream product

• 7451-98-1 3',4'-dihydroxypropiophenone 
• 123-75-1 pyrrolidine 
• 340257-74-1 [5-(1-hydroxy-propyl)-benzo[1,3]dioxol-2-yl]-acetic acid tert-butyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 340257-71-8 (5-formyl-benzo[1,3]dioxol-2-yl)-acetic acid methyl ester 
• 340257-70-7 (5-formyl-benzo[1,3]dioxol-2-yl)-acetic acid tert-butyl ester 
• 4049-39-2 4-benzyloxy-3-hydroxy-benzaldehyde 
• 1579273-98-5 2-(benzyloxy)-5-(1-hydroxyallyl)phenol 

Downstream Products

• 1579273-99-6 4-(1-acetoxypropyl)-1,2-phenylene diacetate 

Relevant articles and documents

Synthesis and evaluation of antiproliferative activity of a novel series of hydroxychavicol analogs

We have recently demonstrated that hydroxychavicol is a major constituent and the most active biophenolic of Piper betel leaves with significant antiproliferative activity in the micro molar range. Herein we present the design, synthesis and evaluation of fifteen novel hydroxychavicol analogs with varying antiproliferative activities in cancer cell lines from two representative tissue types, namely, the prostate and cervix that show very encouraging results compared to the parent compounds. Our long range goal is to develop a structure-activity guided relationship to gain mechanistic insights into novel molecular targets of this class of bioactive molecules for rational drug development. Cytotoxicity-guided experimentation on these novel analogs yielded the following structural factors as the key activity regulators: 1) unlike the hydroxyl substituent at position-4, the position-3 hydroxyl is vital for enhanced activity 2) acetoxyl groups are dispensable for activity as corroborated earlier by others 3) allylic double bonds at 2′C-3′C serve to positively influence antiproliferative activity 4) long saturated side chains at 1′-position negatively regulate antiproliferative activity and 5) maneuvering position-4 with a benzyl group positively impacted the biological activity profile. Most amphiphilic compounds showed moderate to good therapeutic potential as expected on the basis of medicinal chemistry principles. Intriguingly, the most active compound with ten-fold higher activity than the parent molecule was realized by sheer serendipity to employ a silica gel based rearrangement that was further explored using nuclear magnetic resonance spectroscopy and density functional theory calculations. This is the first report to describe strategies for optimal synthesis of a novel series of 15 analogs based upon hydroxychavicol, a simple phytochemical of immense anticancer potential.

SYNTHESIS, ANTI-INFLAMMATORY ACTIVITY AND METABOLISM OF ALKYL ARYL KETONES AND THEIR DERIVATIVES

-

Preparation and pharmacological study of C-isomers of adrenergic amines

-