605-87-8

Usage

Chemical Properties

Tan Solid

Uses

3-Phenanthrol is a metabolite of Phenanthrene.

InChI:InChI=1/C14H10O/c15-12-8-7-11-6-5-10-3-1-2-4-13(10)14(11)9-12/h1-9,15H

Upstream product

• 6335-83-7 4-(2-phenylethyl)phenol 
• 54125-02-9 danishefsky's diene 
• 86-57-7 1-Nitronaphthalene 
• 55149-84-3 2-nitroveratraldehyde 
• 85-01-8 phenanthrene 
• 64-17-5 ethanol 

Downstream Products

• 5346-01-0 1-(6-acetoxy-[3]phenanthryl)-ethanone 
• 7402-91-7 3-hydroxy-9-nitrophenanthrene 
• 100780-04-9 (-)-(R)-3,3'-dihydroxy-4,4'-biphenanthrene 
• 145372-06-1 (aR)-2,2'-dihydroxy-6,6'-dimethoxy-1,1'-binaphthyl 
• 116131-75-0 benzoic acid-(4,9-dichloro-[3]phenanthryl ester) 
• 94688-54-7 Phenyl-phenanthryl-⁽³⁾-aether 
• 74877-24-0 2,2-dihydroxybenzindan-1,3-dione 
• 1892-54-2 3-aminophenanthrene 
• 4733-11-3 phenanthrene 3,4-quinone 
• 4120-78-9 N-(phenanthren-3-yl)acetamide 
• 98681-92-6 4-(3-hydroxy-[4]phenanthrylazo)-benzenesulfonic acid 
• 10386-43-3 4-Formyl-3-phenanthrol 

Relevant academic research and scientific papers

Photocatalysis in dimethyl carbonate green solvent: Degradation and partial oxidation of phenanthrene on supported TiO2

Dimethyl carbonate (DMC) is here proposed-for the first time-as a green organic solvent for photocatalytic synthesis. In this work, the photocatalytic partial oxidation of phenanthrene in dimethyl carbonate (DMC) by using anatase TiO2as the photocatalyst is described as paradigmatic example of a green synthetic process starting from polycyclic aromatic hydrocarbons (PAHs). For comparison, the same reaction carried out also in ethanol, 1-propanol or 2-propanol is reported. The use of DMC as the solvent allowed us to achieve 19% and 23% selectivity towards 9-fluorenone and 6H-benzo[c]chromen-6-one, respectively. The proposed approach may represent both a new green synthetic process and an environmentally friendly route to degradation of PAHs. This journal is

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.

Nitronaphthalenes as Diels-Alder dienophiles

1-Nitronaphthalene, 2-nitronaphthalene and 1,3-dinitronaphthalene react with Danishefsky diene as normal electron demand Diels-Alder dienophiles to give hydroxyphenanthrene derivatives as principal products in reasonable yields. The aromatization is an ex

Metal Arene Complexes in Organic Synthesis. Hydroxylation, Trimethylsilylation, and Carbethoxylation of Some Polycyclic Aromatic Hydrocarbons Utilizing η6-Arene-Chromium Tricarbonyl Complexes

The deprotonation of polycyclic aromatic hydrocarbon (PAH) chromium tricarbonyl complexes (PAH = naphthalene, anthracene, phenanthrene, pyrene, fluoranthene) using an in situ technique where the PAH complex, the base (LiTMP or LDA), and the electrophile (trialkyl borate, trimethylsilyl chloride, or ethyl chloroformate) were placed in solution simultaneously resulted in hydroxylation, trimethylsilylation, or carbethoxylation of the PAH after oxidative workup where the regiochemistry was controlled by steric factors.As a result, substitution at positions of the PAHs not readily available by electrophilic substitution were obtained in some cases.Conditions minimizing isomer mixtures and factors affecting the regiochemistry and the scope of the reaction sequence were examined.