13345-21-6

Basic information

• Product Name: 3-HYDROXYBENZO[A]PYRENE
• Synonyms: 3-HYDROXYBENZO[A]PYRENE;3-hydroxy-benzo(a)pyren;8-hydroxy-3,4-benzpyrene;benzo(a)pyren-3-ol;bp-3-hydroxy;23689, 3-Hydroxybenzo[a]pyrene (purity);3-HYDROXYBENZ(A)PYRENE;3-HOBP
• CAS NO: 13345-21-6
• Molecular Formula: C20H12O
• Molecular Weight: 268.31
• Product Categories: Alphabetic;H;HU - HZ;Aromatics;Metabolites & Impurities;Mutagenesis Research Chemicals;Aromatics, Metabolites & Impurities, Mutagenesis Research Chemicals
• Mol File: 13345-21-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 186-188°C
• 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)
• Storage Temp.: 2-8°C
• PKA: 9.40±0.30(Predicted)
• CAS DataBase Reference: 3-HYDROXYBENZO[A]PYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYBENZO[A]PYRENE(13345-21-6)
• EPA Substance Registry System: 3-HYDROXYBENZO[A]PYRENE(13345-21-6)

Safety Data

• Hazardous Substances Data: 13345-21-6(Hazardous Substances Data)

Usage

Chemical Properties

Dark Yellow to Green Solid

Uses

A metabolite of Benzopyrene (BaP), a carcinogenic component of tobacco smoke implicated in lung cancer.

Safety Profile

Questionable carcinogen withexperimental tumorigenic and neoplastigenic data by skincontact. Human mutation data reported. When heated todecomposition it emits acrid smoke and irritating fumes.

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

Upstream product

• 61441-28-9 1,6,10b,11,12,12a-hexahydro-2H-benzo[def]chrysen-3-one 
• 50-32-8 benzopyrene 
• 63059-68-7 3-methoxybenzopyrene 
• 1094897-81-0 2-(7-methoxynaphthalen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1393793-65-1 3-methoxychrysen-5-ol 
• 1393793-74-2 3-methoxy-5-(trimethylsilylethynyl)chrysene 
• 1393793-75-3 3-methoxy-5-ethynylchrysene 
• 1393793-50-4 2-(2-bromophenyl)-7-methoxynaphthalene 
• 1393793-51-5 ethyl 2-(7-methoxynaphthalen-2-yl)phenylacetate 
• 1393793-67-3 3-methoxychrysen-5-ol trifluoromethanesulfonate 
• 1393793-53-7 2-(7-methoxynaphthalen-2-yl)phenylacetic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 858485-59-3 3-(7H-benz[de]anthracen-3-yl)-propionic acid 
• 339568-41-1 3-(2,3,7,11b-tetrahydro-1H-benz[de]anthracen-3-yl)-propionic acid 

Downstream Products

• 74363-14-7 potassium benzopyren-3-yl sulfate 
• 63059-68-7 3-methoxybenzopyrene 

Related news

3-Hydroxybenzo[a]pyrene in the urine of smokers and non-smokers07/26/2019

The people studied were male volunteers without occupational and dietary exposure to PAH: 27 smokers (10 cigarettes or more) and 27 non-smokers matched for age and socio-professional category. For each person, all the 24 h voided urine samples were reassembled in a single sample. 1-Hydroxypyrene...detailed

Derivatization method for sensitive determination of 3-hydroxybenzo[a]pyrene in human urine by liquid chromatography–electrospray tandem mass spectrometry07/22/2019

While urinary 3-hydroxybenzo[a]pyrene (3-OHBaP) can indicate exposure to carcinogenic benzo[a]pyrene (BaP) in humans, most previous analytical methods could not detect it in the general population due to a lack of sufficient sensitivity. In this study, a new liquid chromatography–electrospray m...detailed

Relevant articles and documents

Inhibition studies on the involvement of flavoprotein reductases in menadione- and nitrofurantoin-stimulated oxyradical production by hepatic microsomes of flounder (Platichthys flesus)

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Genome-to-function characterization of novel fungal P450 monooxygenases oxidizing polycyclic aromatic hydrocarbons (PAHs)

Fungi, particularly the white rot basidiomycetes, have an extraordinary capability to degrade and/or mineralize (to CO2) the recalcitrant fused-ring high molecular weight (≥4 aromatic-rings) polycyclic aromatic hydrocarbons (HMW PAHs). Despite over 30years of research demonstrating involvement of P450 monooxygenation reactions in fungal metabolism of HMW PAHs, specific P450 monooxygenases responsible for oxidation of these compounds are not yet known. Here we report the first comprehensive identification and functional characterization of P450 monooxygenases capable of oxidizing different ring-size PAHs in the model white rot fungus Phanerochaete chrysosporium using a successful genome-to-function strategy. In a genome-wide P450 microarray screen, we identified six PAH-responsive P450 genes (Pc-pah1-Pc-pah6) inducible by PAHs of varying ring size, namely naphthalene, phenanthrene, pyrene, and benzo(a)pyrene (BaP). Using a co-expression strategy, cDNAs of the six Pc-Pah P450s were cloned and expressed in Pichia pastoris in conjunction with the homologous P450 oxidoreductase (Pc-POR). Each of the six recombinant P450 monooxygenases showed PAH-oxidizing activity albeit with varying substrate specificity towards PAHs (3-5 rings). All six P450s oxidized pyrene (4-ring) into two monohydroxylated products. Pc-Pah1 and Pc-Pah3 oxidized BaP (5-ring) to 3-hydroxyBaP whereas Pc-Pah4 and Pc-Pah6 oxidized phenanthrene (3-ring) to 3-, 4-, and 9-phenanthrol. These PAH-oxidizing P450s (493-547 aa) are structurally diverse and novel considering their low overall homology (12-23%) to mammalian counterparts. To our knowledge, this is the first report on specific fungal P450 monooxygenases with catalytic activity toward environmentally persistent and highly toxic HMW PAHs.

Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer

Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants produced in the combustion of organic matter. PAHs are present in automobile exhaust and tobacco smoke, and they have recently been designated as human carcinogens. Current ev