PHENANTHRENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10
Molecular Weight	178.2292
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CC2=CC=C3C=CC=CC3=C2C=C1

InChI

InChIKey=YNPNZTXNASCQKK-UHFFFAOYSA-N

InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H

HIDE SMILES / InChI

Description
Sources: https://www.cdc.gov/biomonitoring/Phenanthrene_BiomonitoringSummary.html | https://archive.epa.gov/epawaste/hazard/wastemin/web/pdf/phenanth.pdf | https://www.ncbi.nlm.nih.gov/pubmed/30514863

Phenanthrene is one of a group of chemicals called polycyclic aromatic hydrocarbons, PAHs. Phenanthrene is one of the most abundant PAHs found in continental shelf sediment of the South China Sea and is on the EPA’s Priority Pollutant list. Phenanthrene can affect different organisms through some potential mechanism such as the aryl hydrocarbon receptor (AHR) agonists, reproductive endocrine disruptor and photosynthesis stimulation. Phenanthrene is used in manufacturing dyestuffs and explosives and in biological research. Sources of phenanthrene include diesel fuel exhaust, coal tar pitch and tobacco smoke. Phenanthrene has been found in particle emissions from natural gas combustion and municipal incinerator waste, and in the particulates present in ambient air pollution near high vehicular traffic and industrial or urban areas.

Approval Year

PubMed

Title	Date	PubMed
Occurrence of organic pollutants in recovered soil fines from construction and demolition waste.	2001	11699628
Crotoflavol, a new phenanthrene from Croton flavens.	2001	11561448
Contamination of polycyclic aromatic hydrocarbons in surface sediments of mangrove swamps.	2001	11504348
Partition of polycyclic aromatic hydrocarbons on organobentonites from water.	2001 Apr	11590729
[Degradation of phenanthrene and pyrene in contaminated soil by immobilized Zoogloea sp. and Fusarium sp].	2001 Aug	11758402
Multiple mutations at the active site of naphthalene dioxygenase affect regioselectivity and enantioselectivity.	2001 Aug	11641767
Development and certification of a coal fly ash certified reference material for selected polycyclic aromatic hydrocarbons.	2001 Aug	11583083
Biotransformation of phenanthrene and 1-methoxynaphthalene with Streptomyces lividans cells expressing a marine bacterial phenanthrene dioxygenase gene cluster.	2001 Aug	11577717
Sorption of organic contaminants in a fractured chalk formation.	2001 Aug	11513399
Impact of sediment manipulation on the bioaccumulation of polycyclic aromatic hydrocarbons from field-contaminated and laboratory-dosed sediments by an oligochaete.	2001 Aug	11491559
Heritability of resistance to individual contaminants and to contaminant mixtures in the sheepshead minnow (Cyprindon variegatus).	2001 Aug	11491558
Photolytic behavior of polycyclic aromatic hydrocarbons in diesel particulate matter deposited on the ground.	2001 Aug 1	11505989
Interfacial nonradiative energy transfer in responsive core-shell hydrogel nanoparticles.	2001 Aug 29	11516270
A transcriptional luxAB reporter fusion responding to fluorene in Sphingomonas sp. LB126 and its initial characterisation for whole-cell bioreporter purposes.	2001 Dec	11766960
Single and combined effects of sediment-associated PAHs on three species of freshwater macroinvertebrates.	2001 Dec	11759569
Degradation of phenanthrene in river sediment under nitrate-reducing conditions.	2001 Dec	11692206
Soil biosensor for the detection of PAH toxicity using an immobilized recombinant bacterium and a biosurfactant.	2001 Dec	11679243
Impacts of heterogeneous organic matter on phenanthrene sorption: different soil and sediment samples.	2001 Dec 1	11770772
[Use of Pseudomonas and Achromobacter species bacteria--degraders of surface-active agents--for detection and destruction of polycyclic aromatic hydrocarbons].	2001 Jan-Feb	11599420
[Transportation and transformation of 14C-phenanthrene in closed chamber (nutrient solution-lava-plant-air) system].	2001 Jun	11758435
[Co-metabolic degradation of pyrene in soil].	2001 Jun	11758434
Convergent and divergent points in catabolic pathways involved in utilization of fluoranthene, naphthalene, anthracene, and phenanthrene by Sphingomonas paucimobilis var. EPA505.	2001 Jun	11571621
[Study of carcinogenic hazards of smoking kiln waste fumes].	2001 Mar-Apr	11494480
Biodegradation of polycyclic aromatic hydrocarbons by Sphingomonas strains isolated from the terrestrial subsurface.	2001 May	11494104
Aliphatic and aromatic hydrocarbons in sediments of Santos and Cananéia, SP, Brazil.	2001 Nov	11763217
Occurrence of polycyclic aromatic hydrocarbons in sewage sludge and their contribution to its toxicity in the toxalert 100 bioassay.	2001 Nov	11695588
Assessing the aerobic biodegradability of 14 hydrocarbons in two soils using a simple microcosm/respiration method.	2001 Nov	11695585
Photoinduced toxicity of retene to Daphnia magna under enhanced UV-B radiation.	2001 Nov	11680764
Objective threshold selection procedure (OTS) for segmentation of scanning laser confocal microscope images.	2001 Nov	11576681
Using structures formed by dirhodium tetra(trifluoroacetate) with polycyclic aromatic hydrocarbons to prospect for maximum pi-electron density: Hückel calculations get it right.	2001 Nov 28	11716722
Degradation of crude oil by marine cyanobacteria.	2001 Oct	11759698
The aegean sea oil spill in the Galicia Coast (NW Spain). I. Distribution and fate of the crude oil and combustion products in subtidal sediments.	2001 Oct	11693644
Cytotoxic quaternary alkaloids from the flowers of Narcissus tazetta.	2001 Oct	11683132
Phenanthrene derivatives from the orchid Coelogyne cristata.	2001 Oct	11576602
Effects of a non-ionic surfactant (Tween-80) on the mineralization, metabolism and uptake of phenanthrene in wheat-solution-lava microcosm.	2001 Oct	11572593
Enhanced degradation of polycyclic aromatic hydrocarbons by biodegradation combined with a modified Fenton reaction.	2001 Oct	11572585
Detection of mega plasmid from polycyclic aromatic hydrocarbon-degrading Sphingomonas sp. strain KS14.	2001 Oct	11545268
A novel cloud-point extraction process for preconcentrating selected polycyclic aromatic hydrocarbons in aqueous solution.	2001 Oct 1	11642455
On-line identification method in column liquid chromatography: UV resonance Raman spectroscopy.	2001 Oct 15	11681475
Metabolism of anthracene by a Rhodococcus species.	2001 Oct 16	11682202
New substances for intraocular tamponades: perfluorocarbon liquids, hydrofluorocarbon liquids and hydrofluorocarbon-oligomers in vitreoretinal surgery.	2001 Sep	11688661
Bioavailability of solid and non-aqueous phase liquid (NAPL)-dissolved phenanthrene to the biosurfactant-producing bacterium Pseudomonas aeruginosa 19SJ.	2001 Sep	11683866
Microbial degradation of phenanthrene and pyrene in a two-liquid phase-partitioning bioreactor.	2001 Sep	11601632
Effects of chitin on microbial emulsification, mineralization potential, and toxicity of bunker C fuel oil.	2001 Sep	11585070
Hydrocarbon accumulation by picocyanobacteria from the Arabian Gulf.	2001 Sep	11556921
Determination of hydrocarbons in old creosote contaminated soil using headspace solid phase microextraction and GC-MS.	2001 Sep	11545529
Influence of heavy organic pollutants of anthropic origin on PAH retention by kaolinite.	2001 Sep	11545528
Sorption of phenanthrene by reference smectites.	2001 Sep 1	11563646
PAH degradation by UV/H2O2 in perfluorinated surfactant solutions.	2002 Jan	11766808
Solubilization of polycyclic aromatic hydrocarbons by perfluorinated surfactant micelles.	2002 Jan	11766807

Name

Type

Language

PHENANTHRENE

Systematic Name

English

RAVATITE

Common Name

English

PHENANTHRENE [MI]

Common Name

English

(3)HELICENE

Systematic Name

English

PHENANTHRENE [HSDB]

Common Name

English

NSC-26256

Code

English

PHENANTHRENE [IARC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C761