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1,2-Benzanthraquinone

$72

  • Brand : BIOFRON

  • Catalogue Number : BN-O1079

  • Specification : 98%(HPLC)

  • CAS number : 2498-66-0

  • Formula : C18H10O2

  • Molecular Weight : 258.3

  • PUBCHEM ID : 17253

  • Volume : 5mg

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Catalogue Number

BN-O1079

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

258.3

Appearance

Botanical Source

Structure Type

Category

SMILES

C1=CC=C2C(=C1)C=CC3=C2C(=O)C4=CC=CC=C4C3=O

Synonyms

Tetraphene-7,12-dione/Sirius Yellow G/benzanthraquinone/Tetraphen-7,12-dion/NAPHTHANTHRAQUINONE/7,12-Tetraphenedione/Benz[a]anthracene-7,12-dione/1,2-BENZOANTHRAQUINONE/Benzanthracene-7,12-dione/1,2-Benzanthraquinone

IUPAC Name

benzo[a]anthracene-7,12-dione

Density

1.3±0.1 g/cm3

Solubility

Flash Point

175.5±17.4 °C

Boiling Point

472.5±15.0 °C at 760 mmHg

Melting Point

169-171 °C(lit.)

InChl

InChl Key

LHMRXAIRPKSGDE-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:2498-66-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

26141390

Abstract

Polycyclic aromatic hydrocarbons (PAHs) are priority environmental contaminants that exhibit mutagenic, carcinogenic, proinflammatory, and teratogenic properties. Oxygen-substituted PAHs (OPAHs) are formed during combustion processes and via phototoxidation and biological degradation of parent (unsubstituted) PAHs. Despite their prevalence both in contaminated industrial sites and in urban air, OPAH mechanisms of action in biological systems are relatively understudied. Like parent PAHs, OPAHs exert structure-dependent mutagenic activities and activation of the aryl hydrocarbon receptor (AHR) and cytochrome p450 metabolic pathway. Four-ring OPAHs 1,9-benz-10-anthrone (BEZO) and benz(a)anthracene-7,12-dione (7,12-B[a]AQ) cause morphological aberrations and induce markers of oxidative stress in developing zebrafish with similar potency, but only 7,12-B[a]AQ induces robust Cyp1a protein expression. We investigated the role of the AHR in mediating the toxicity of BEZO and 7,12-B[a]AQ, and found that knockdown of AHR2 rescued developmental effects caused by both compounds. Using RNA-seq and molecular docking, we identified transcriptional responses that precede developmental toxicity induced via differential interaction with AHR2. Redox-homeostasis genes were affected similarly by these OPAHs, while 7,12-B[a]AQ preferentially activated phase 1 metabolism and BEZO uniquely decreased visual system genes. Analysis of biological functions and upstream regulators suggests that BEZO is a weak AHR agonist, but interacts with other transcriptional regulators to cause developmental toxicity in an AHR-dependent manner. Identifying ligand-dependent AHR interactions and signaling pathways is essential for understanding toxicity of this class of environmentally relevant compounds.

KEYWORDS

OPAH; RNA-seq; aryl hydrocarbon receptor; benz(a)anthracene-7,12-dione; benzanthrone; zebrafish.

Title

Ligand-Specific Transcriptional Mechanisms Underlie Aryl Hydrocarbon Receptor-Mediated Developmental Toxicity of Oxygenated PAHs

Author

B C Goodale 1, J La Du 2, S C Tilton 3, C M Sullivan 4, W H Bisson 2, K M Waters 5, R L Tanguay 6

Publish date

2015 Oct

PMID

25395203

Abstract

The objective of this study was to develop a novel analytical chemistry method, comprised of a coupled high-performance liquid chromatography-gas chromatography/mass spectrometry system (LC-GC/MS) with low detection limits and high selectivity, for the identification and determination of oxygenated polycyclic aromatic hydrocarbons (OPAHs) and polycyclic aromatic hydrocarbons (PAHs) in urban air and diesel particulate matter. The linear range of the four OPAHs, which include 9,10-anthraquinone, 4H-cyclopenta[def]phenanthrene-4-one, benzanthrone, and 7,12-benz[a]anthraquinone, was 0.7 pg-43.3 ng with limits of detection (LODs) and limits of quantification (LOQs) on the order of 0.2-0.8 and 0.7-1.3 pg, respectively. The LODs in this study are generally lower than values reported in the literature, which can be explained by using large-volume injection. The recoveries of the OPAHs spiked onto glass fiber filters using two different pressurized liquid extraction (PLE) methods were in the ranges of 84-107 and 67-110 %, respectively. The analytical protocols were validated using the following National Institute of Standards and Technology standard reference materials: SRM 1649a (Urban Dust), SRM 1650b (Diesel Particulate Matter), and SRM 2975 (Diesel Particulate Matter, Industrial Forklift). The measured mass fractions of the OPAHs in the standard reference materials (SRMs) in this present study are higher than the values from the literature, except for benzanthrone in SRM 1649a (Urban Dust). In addition to the OPAHs, 44 PAHs could be detected and quantified from the same particulate extract used in this protocol. Using data from the literature and applying a two-sided t test at the 5 % level using Bonferroni correction, significant differences were found between the tested PLE methods for individual PAHs. However, the measured mass fractions of the PAHs were comparable, similar to, or higher than those previously reported in the literature.

Title

Determination of Oxygenated and Native Polycyclic Aromatic Hydrocarbons in Urban Dust and Diesel Particulate Matter Standard Reference Materials Using Pressurized Liquid Extraction and LC-GC/MS

Author

Trifa M Ahmed 1, Christoffer Bergvall, Magnus aberg, Roger Westerholm

Publish date

2015 Jan;

PMID

1279414

Abstract

We evaluated the influence of near-ultraviolet light (UVA) on the cytotoxicity and genotoxicity of 7 polycyclic aromatic hydrocarbons (PAH) in larvae of the amphibian Pleurodeles waltl. Benz[a]anthracene (BA), 7,12-benz[a]anthraquinone (BAQ) and anthracene (Ac) proved to be lethal at low doses (some ppb), and the following order of genotoxicity was observed: BA approximately BAQ > DMBA > DMA (9,10-dimethylanthracene). Ac, AQ (9,10-anthraquinone) and DBA (dibenz[a,h]anthracene) were not found to be clastogenic. In the larvae reared in normal conditions (subdued natural daylight/darkness alternation) or in continuous darkness, the BA derivatives were shown to be more genotoxic than BA itself: DMBA > BAQ > BA; BA (> or = 187.5 ppb) slightly increased the level of micronuclei in circulating erythrocytes, while DMBA was strongly clastogenic, in line with their reported carcinogenicity. In other experiments, rearing media alone (i.e., water containing BA, BAQ or DMBA) were UVA-irradiated for 24 h, and then tested on larvae in the dark (‘IR-UV/dark’ conditions). Photodegradation of BA (50 and 100 ppb) gave rise to clastogenic products. By contrast, DMBA (12.5, 25 or 50 ppb) was destroyed by UVA, and we suggested that any potentially mutagenic photoproducts formed were not in sufficient amounts to yield a positive response in the newt micronucleus test.

Title

Influence of Lighting Conditions on Toxicity and Genotoxicity of Various PAH in the Newt in Vivo

Author

M Fernandez 1, J L'Haridon

Publish date

1992 Nov;


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