Benzo[ghi]perylene standard solution - 2000μg/ml in Toluene , CAS No.191-24-2

CAS: 191-24-2 Cat. No.: B141127 Molecular Weight: 276.33 Beilstein Registry Number: 1913029 EC Number: 205-883-8

GRADE & PURITY 2000μg/ml in Toluene

Synonyms

AMY7681 | H11449 | A813479 | CCRIS 784 | hexacyclo[12.8.0.02,11.03,8.04,21.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaene | HSDB 6177 | C22H12 | NCGC00163974-01 | B2983 | Benzo(g,h,i)perylene | Benzo[ghi]perylene, BCR(R) certified Refer

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

AMY7681 | H11449 | A813479 | CCRIS 784 | hexacyclo[12.8.0.02, 11.03, 8.04, 21.017, 22]docosa-1(14), 2(11), 3(8), 4, 6, 9, 12, 15, 17(22), 18, 20-undecaene | HSDB 6177 | C22H12 | NCGC00163974-01 | B2983 | Benzo(g, h, i)perylene | Benzo[ghi]perylene, BCR(R) certified Refer

Specifications & Purity

2000μg/ml in Toluene

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1=CC2=C3C(=C1)C4=CC=CC5=C4C6=C(C=C5)C=CC(=C36)C=C2
• IUPAC Name: hexacyclo[12.8.0.02,11.03,8.04,21.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaene
• InChIKey: GYFAGKUZYNFMBN-UHFFFAOYSA-N
• INCHI: 1S/C22H12/c1-3-13-7-9-15-11-12-16-10-8-14-4-2-6-18-17(5-1)19(13)21(15)22(16)20(14)18/h1-12H
• Isomeric SMILES: C1=CC2=C3C(=C1)C4=CC=CC5=C4C6=C(C=C5)C=CC(=C36)C=C2
• WGK Germany: 3
• RTECS: DI6200500
• UN Number: 3077
• Packing Group: III
• Molecular Weight: 276.33
• Beilstein: 1913029
• Reaxy-Rn: 1913029
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1913029&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Pyrenes
      • Subclass Benzopyrenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Pyrenes
• Subclass: Benzopyrenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzopyrenes
• Alternative Parents: Triphenylenes Anthracenes Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Benzo-e-pyrene - Triphenylene - Phenanthrene - Anthracene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
• External Descriptors: ortho- and peri-fused polycyclic arene

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RXRA Tclin Retinoid X receptor alpha (3637 Activities)

Discover Target: RXRA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

Discover Target: TP53

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

Discover Target: Ppard

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Boil Point(°C): 542°C
• Melt Point(°C): 276-279°C
• Molecular Weight: 276.300 g/mol
• XLogP3: 6.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 276.094 Da
• Monoisotopic Mass: 276.094 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 411.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Shaolin Xie, Bing Yang, Siying Li, Liangjun Ge, Min Li, Qingshi Chen, Xian Qing, Jixing Zou.  (2023)  Generation and application of a novel transgenic zebrafish line Tg(GAcyp1a:eGFP/Luc) as an in vivo assay to sensitive and specific monitoring of DLCs in the environment.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:37729807] [10.1016/j.ecoenv.2023.115471]

2. Yuanji Gao, Hongru Feng, Bing Xia, Lei He, Congling Yang, Lijuan Zhao, Yuanjiang Pan.  (2023)  Ultrasensitive and Green Bubbling Extraction Strategies: An Extensible Solvent-Free Re-Enrichment Approach for Ultratrace Pollutants in Aqueous Samples.  ANALYTICAL CHEMISTRY,      [PMID:37624983] [10.1021/acs.analchem.3c02807]

3. Guanqing Jiang, Xu Song, Jiaying Xie, Tongxing Shi, Qiaoyuan Yang.  (2023)  Polycyclic aromatic hydrocarbons (PAHs) in ambient air of Guangzhou city: Exposure levels, health effects and cytotoxicity.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:37544068] [10.1016/j.ecoenv.2023.115308]

4. Shaolin Xie, Yongyong Feng, Aiguo Zhou, Zhiyuan Lu, JixingZou.  (2023)  Comparative analysis of two new zebrafish models: The cyp1a low-expression line and cyp1a knockout line under PAHs exposure.  GENE,      [PMID:36966979] [10.1016/j.gene.2023.147391]

5. Ke Min, Yong Li, Yue Lin, Xuezhi Yang, Zigu Chen, Bo Chen, Ming Ma, Qian Liu, Guibin Jiang.  (2022)  Mass Spectrometry Imaging Strategy for In Situ Quantification of Soot in Size-Segregated Air Samples.  ANALYTICAL CHEMISTRY,      [PMID:36301736] [10.1021/acs.analchem.2c01443]

6. Zifang Peng, Wenfen Zhang, Dan Yin, Xu Zhang, Shuo Liu, Wuduo Zhao, Jian Mao, Yanhao Zhang, Jianping Xie.  (2022)  Novel magnetic single-layer nano-MXene as a highly effective adsorbent and new SALDI-TOF-MS matrix for enrichment and rapid determination of p-Phenylenediamine antioxidants in water.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2022.139978]

7. Li Zhansheng, Zhao Hongxia, Li Xintong, Bekele Tadiyose Girma.  (2021)  Characteristics and sources of environmentally persistent free radicals in PM2.5 in Dalian, Northeast China: correlation with polycyclic aromatic hydrocarbons.  ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,  29  (17): (24612-24622).  [PMID:34822091] [10.1007/s11356-021-17688-9]

8. Yue Lin, Xiu Huang, Yongchun Liu, Dong Cao, Dawei Lu, Zeming Feng, Qian Liu, Zhenyu Lin, Guibin Jiang.  (2021)  Identification, Quantification, and Imaging of the Biodistribution of Soot Particles by Mass Spectral Fingerprinting.  ANALYTICAL CHEMISTRY,      [PMID:33881821] [10.1021/acs.analchem.0c05180]

9. Xiao Sun, Jing Li, Li Xu.  (2018)  Synthesis of penetrable poly(methacrylic acid-co-ethylene glycol dimethacrylate) microsphere and its HPLC application in protein separation.  TALANTA,      [PMID:29759187] [10.1016/j.talanta.2018.03.080]

10. Bin Qiao, Yansong Li, Pan Hu, Yu Sun, Zhaozhao Si, Shiying Lu, Honglin Ren, Zengshan Liu, Ying Zhang, Lei Meng, Yu Zhou.  (2018)  EuNPs-MAb fluorescent probe based immunochromatographic strip for rapid and sensitive detection of fluorene.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.01.231]

11. Yong Li, Ling Long, Jing Ge, Li-xuan Yang, Jin-jin Cheng, Ling-xiang Sun, Changying Lu, Xiang-yang Yu.  (2017)  Presence, distribution and risk assessment of polycyclic aromatic hydrocarbons in rice-wheat continuous cropping soils close to five industrial parks of Suzhou, China.  CHEMOSPHERE,      [PMID:28641227] [10.1016/j.chemosphere.2017.06.055]

12. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu.  (2015)  Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase.  TALANTA,      [PMID:26695288] [10.1016/j.talanta.2015.09.009]

13. Zifang Peng, Yanhao Zhang, Yide Dong, Wuduo Zhao, Jian Mao, Qidong Zhang, Gangfeng Ouyang, Shusheng Zhang, Jianping Xie.  (2025)  A cheap 3D-printed boron, nitrogen, sulfur-MXene quantum dots-based target plate for multi-dimensional MALDI MS imaging of small-molecule environmental pollutants.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.160596]

14. Yuqian Li, Haomin Chen, Wei Li, Beidou Xi, Caihong Huang.  (2025)  A novel immobilized bacteria consortium enhanced remediation efficiency of PAHs in soil: Insights into key removal mechanism and main driving factor.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:39787861] [10.1016/j.jhazmat.2025.137144]

15. Qian Zhang, Xinyan Xu, Chenzhuo Song, Dengke Zhang, Yi Kong, Xinyi Cui.  (2024)  Effect of UV exposure and natural aging on the in vitro PAHs bioaccessibility associated with tire wear particles in soil.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:39197782] [10.1016/j.scitotenv.2024.175751]

16. Xintong Li, Baocheng Qu, Jingyao Wang, Hongxia Zhao.  (2024)  Photoformation of Environmentally Persistent Free Radicals During Phototransformation of Poly-Cyclic Aromatic Hydrocarbons (PAHs) on Particles in an Aqueous Solution: The Hydrogenation of PAHs and Effect of Co-Existing Water Matrix Factors.  Toxics,  12  (11): (796).  [PMID:39590976] [10.3390/toxics12110796]

17. Linfeng Chen, Xike Tian, Yong Li, Chao Yang, Yunjie Huang, Yulun Nie.  (2021)  Rapid and sensitive screening of multiple polycyclic aromatic hydrocarbons by a reusable fluorescent sensor array.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:34785436] [10.1016/j.jhazmat.2021.127694]

18. Sili Chen, Liqin Xiong, Xinlan Wu, Lu Chen, Junwei Zhang, Guanqing Jiang, Xin Li, Qiaoyuan Yang.  (2025)  Molecular mechanisms by which benzo[ghi]perylene promotes cell proliferation and DNA damage via downregulation of the chimeric RNA TVP23C-CDRT4/miR-24-3p Axis.  TOXICOLOGY LETTERS,      [PMID:] [10.1016/j.toxlet.2025.111755]

19. Sili Chen, Xiangyu Ding, Tao Zheng, Hao Deng, Qiaoyuan Yang.  (2025)  The CYP1A1/ chimeric RNA RPL17-C18orf32 axis mediates Benzo[ghi]perylene induced-respiratory toxicity and DNA damage in vitro and in vivo.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:41218492] [10.1016/j.ecoenv.2025.119377]