13345-23-8

Basic information

• Product Name: 1-hydroxybenzo(a)pyrene
• Synonyms: 1-hydroxybenzo(a)pyrene;Benzo[a]pyren-1-ol
• CAS NO: 13345-23-8
• Molecular Formula: C20H12 O
• Molecular Weight: 268.32
• Mol File: 13345-23-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 371.47°C (rough estimate)
• Flash Point: 252.9°C
• Appearance: /
• Density: 1.0921 (rough estimate)
• Vapor Pressure: 9.85E-12mmHg at 25°C
• Refractive Index: 1.6220 (estimate)
• CAS DataBase Reference: 1-hydroxybenzo(a)pyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-hydroxybenzo(a)pyrene(13345-23-8)
• EPA Substance Registry System: 1-hydroxybenzo(a)pyrene(13345-23-8)

Safety Data

• Hazardous Substances Data: 13345-23-8(Hazardous Substances Data)

Usage

Description

1-Hydroxybenzo(a)pyrene is a monohydroxy benzo(a)pyrene derivative that exhibits estrogenic activity and has the ability to bind to estrogen receptors (ERs).

Uses

Used in Pharmaceutical Industry:
1-Hydroxybenzo(a)pyrene is used as a pharmaceutical agent for its estrogenic activity, as it can bind to estrogen receptors (ERs). This property makes it a potential candidate for the development of drugs targeting estrogen-related conditions and diseases.
Used in Research and Development:
1-Hydroxybenzo(a)pyrene is used as a research tool for studying the effects of estrogenic compounds on biological systems. Its ability to bind to estrogen receptors makes it valuable in understanding the mechanisms of estrogen action and the development of new therapeutic strategies for estrogen-related disorders.
Used in Environmental Monitoring:
1-Hydroxybenzo(a)pyrene, due to its estrogenic activity, can be used in environmental monitoring to detect and assess the presence of endocrine-disrupting chemicals in the environment. This can help in evaluating the potential impact of these chemicals on wildlife and human health.

Safety Profile

Human mutation data reported.When heated to decomposition it emits acrid smoke andirritating fumes.

InChI:InChI=1/C20H12O/c21-18-10-7-12-5-6-14-11-13-3-1-2-4-15(13)16-8-9-17(18)19(12)20(14)16/h1-11,21H

Upstream product

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• 107616-84-2 1-bromo-7,8,9,10-tetrahydrobenzopyren-7-one 
• 123125-87-1 3-(8-Methoxy-pyren-1-yl)-propan-1-ol 
• 123125-79-1 7,8,9,10-Tetrahydro-benzo[def]chrysene-1,7-diol 
• 123125-89-3 4-(8-Methoxy-pyren-1-yl)-butyronitrile 
• 123125-82-6 3-(8-Methoxy-pyren-1-yl)-propionic acid 
• 123125-92-8 1-methoxy-9,10-dihydrobenzo[a]pyren-7(8H)-one 

Relevant articles and documents

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Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene

Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed Suzuki, Sonogashira, and Hartwig cross-coupling reactions combined with PtCl2-catalyzed cyclization of acetylenic compounds. This synthetic method requires fewer steps, employs milder conditions, and product isolation is simpler than conventional methods of PAH synthesis. The syntheses of 13C4-BaP and 13C4-BaP-8-ol each require only four steps, and the 13C-atoms are all introduced in a single step. 13C4-BaP-8-ol serves as the synthetic precursor of all the oxidized metabolites of 13C-BaP implicated in initiation of cancer. The isotopic purities of the synthetic 13C 4-BaP metabolites were estimated to be ≥99.9%.

Synthesis of the Phenolic Derivatives of Highly Tumorigenic trans-7,8-Dihydroxy-7,8-dihydrobenzopyrene

Two isomeric phenolic derivatives of trans-7,8-dihydro-7,8-dihydroxybenzopyrene (42), 3,7,8-trihydroxy-trans-7,8-dihydrobenzopyrene (40), and 1,7,8-trihydroxy-trans-7,8-dihydrobenzopyrene (41), have been prepared in order to probe their relevance