72378-87-1

Basic information

• Product Name: 3-Acetoxydibenz[a,h]anthracene
• Synonyms: Benzo[k]benz[a]anthracen-3-ol 3-Acetate;Dibenz[a,h]anthracen-3-ol Acetate
• CAS NO: 72378-87-1
• Molecular Formula: C₂₄H₁₆O₂
• Molecular Weight: 336.38
• Product Categories: Detergents;Mutagenesis Research Chemicals;Aromatics;Intermediates
• Mol File: 72378-87-1.mol

Chemical Properties

• Melting Point: 247-248°C
• Boiling Point: 581.5 °C at 760 mmHg
• Flash Point: 170.5 °C
• Appearance: /
• Density: 1.276 g/cm³
• Vapor Pressure: 1.63E-13mmHg at 25°C
• Refractive Index: 1.764
• CAS DataBase Reference: 3-Acetoxydibenz[a,h]anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetoxydibenz[a,h]anthracene(72378-87-1)
• EPA Substance Registry System: 3-Acetoxydibenz[a,h]anthracene(72378-87-1)

Safety Data

• Hazardous Substances Data: 72378-87-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Acetoxydibenz[a,h]anthracene is used as a synthetic intermediate for the production of 3-Hydroxydibenz[a,h]anthracene, which is a known metabolite of DBA (Dibenz[a,h]anthracene) (D417010). This metabolite plays a significant role in the study of the metabolic pathways of polycyclic aromatic hydrocarbons and their potential impact on human health and the environment.
Used in Pharmaceutical Research:
3-Acetoxydibenz[a,h]anthracene can be utilized in pharmaceutical research as a starting material for the development of new drugs and therapeutic agents. Its unique chemical structure allows for the exploration of its potential biological activities and interactions with various biological targets, which may lead to the discovery of novel treatments for various diseases and conditions.
Used in Environmental Studies:
As a metabolite of DBA, 3-Acetoxydibenz[a,h]anthracene can be employed in environmental studies to understand the fate and transport of polycyclic aromatic hydrocarbons in the environment. This knowledge is crucial for assessing the potential risks associated with exposure to these compounds and for developing strategies to mitigate their impact on ecosystems and human health.

InChI:InChI=1/C24H16O2/c1-15(25)26-20-10-11-22-17(12-20)8-9-19-13-23-18(14-24(19)22)7-6-16-4-2-3-5-21(16)23/h2-14H,1H3

Upstream product

• 66267-14-9 trans-3,4-diacetoxy-1,2,3,4-tetrahydrodibenzanthracene 
• 1421-80-3 3-hydroxydibenzanthracene 
• 72378-86-0 3-acetoxy-1,2-dihydrodibenzanthracene 

Downstream Products

• 1421-80-3 3-hydroxydibenzanthracene 

Relevant articles and documents

Synthesis and Properties of the Seven Isomeric Phenols of Dibenzanthracene

The seven possible monohydroxy derivatives of dibenzanthracene (4a-g) were synthesized by using the reductive cyclization of o-naphthoylnaphthoic acids with hydroiodic acid-red phosphorus.The mass, 1H NMR, and UV spectral properties are discussed in detail as a means of identifying metabolically formed phenols of dibenzanthracene.

Synthesis of Biologically Active Metabolites of Dibenzanthracene

Syntheses are described of the trans 1,2- and 3,4-dihydro diol metabolites (3a and 1a) of dibenzanthracene (DBA) and the corresponding diol epoxide derivatives 4 and 2, implicated as the ultimate carcinogenic metabolites of DBA.The synheses of 1a and 3a are accomplished from DBA via lithium-ammonia reduction to 1,4,7,8,11,14-hexahydrodibenzanthracene, base-catalyzed isomerization, Prevost reaction, dehydrogenation, and basic methanolysis.This approach involves considerably fewer steps and affords superior overall yields than obtainable by more conventional methods entailing multistep ring construction.Epoxidation of 1a affords stereospecifically the anti diol epoxide isomer 2, whereas similar reaction of 3a furnishes a mixture of the corresponding syn and anti diol epoxide isomers in 3:1 ratio.Biological evidence implicates 1a and 2 as proximate and ultimate carcinogenic forms, respectively, of DBA.Synthesis of 3-hydroxydibenzanthracene, also known to be a metabolite of DBA, is also described.