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2,2',3,4,4',5,6-Heptachlorobiphenyl

PubChem CID
53038
Structure
2,2',3,4,4',5,6-Heptachlorobiphenyl_small.png
2,2',3,4,4',5,6-Heptachlorobiphenyl_3D_Structure.png
Molecular Formula
Synonyms
  • 2,2',3,4,4',5,6-Heptachlorobiphenyl
  • 74472-47-2
  • E1XED1DKLM
  • UNII-E1XED1DKLM
  • PCB 181
Molecular Weight
395.3 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-28
  • Modify:
    2024-12-14
Description
2,2',3,4,4',5,6-Heptachlorobiphenyl is one of 209 polychlorinated biphenyls (PCBs). PCBs are a group of synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. They were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate and cause harmful health effects. However, PCBs do not break down readily and are still found in the environment. (L4)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2,2',3,4,4',5,6-Heptachlorobiphenyl.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2,3,4,5-pentachloro-6-(2,4-dichlorophenyl)benzene
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C12H3Cl7/c13-4-1-2-5(6(14)3-4)7-8(15)10(17)12(19)11(18)9(7)16/h1-3H
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

DJEUXBQAKBLKPO-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=CC(=C(C=C1Cl)Cl)C2=C(C(=C(C(=C2Cl)Cl)Cl)Cl)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

C12H3Cl7
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

74472-47-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 DSSTox Substance ID

2.3.5 Nikkaji Number

2.3.6 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
395.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
7.6
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
393.802494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
391.805444 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
0Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
296
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 3
View All
NIST Number
334772
Library
Main library
Total Peaks
181
m/z Top Peak
394
m/z 2nd Highest
396
m/z 3rd Highest
324
Thumbnail
Thumbnail
2 of 3
View All
NIST Number
80790
Library
Replicate library
Total Peaks
205
m/z Top Peak
394
m/z 2nd Highest
396
m/z 3rd Highest
324
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are trasported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html
T6: World Health Organization (1993). Environ Health Criteria 140: Polychlorniated Biphenyls and Terphenyls.

8 Use and Manufacturing

8.1 Uses

PCBs were used as coolants and lubricants in transformers, capacitors, and other electrical devices (such as fluorescent lights and refridgerators) produced before 1977. PCBs may contaminate the air and water near hazardous waste sites. In addition, PCBs bioaccumulate in the environment and may be found in fish, meat, and dairy products. (L4)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports. Pictograms displayed are for < 0.1% (0 of 3) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 3 of 3 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 3 of 3 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 3 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Not Classified

10 Toxicity

10.1 Toxicological Information

10.1.1 Toxicity Summary

The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)
A30: Troisi GM, Haraguchi K, Kaydoo DS, Nyman M, Aguilar A, Borrell A, Siebert U, Mason CF: Bioaccumulation of polychlorinated biphenyls (PCBs) and dichlorodiphenylethane (DDE) methyl sulfones in tissues of seal and dolphin morbillivirus epizootic victims. J Toxicol Environ Health A. 2001 Jan 12;62(1):1-8. PMID:11205532
A3: Aoki Y: Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters--what we have learned from Yusho disease. Environ Res. 2001 May;86(1):2-11. PMID:11386736
A4: Safe S, Bandiera S, Sawyer T, Robertson L, Safe L, Parkinson A, Thomas PE, Ryan DE, Reik LM, Levin W, et al.: PCBs: structure-function relationships and mechanism of action. Environ Health Perspect. 1985 May;60:47-56. PMID:2992927
A66: Kester MH, Bulduk S, Tibboel D, Meinl W, Glatt H, Falany CN, Coughtrie MW, Bergman A, Safe SH, Kuiper GG, Schuur AG, Brouwer A, Visser TJ: Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology. 2000 May;141(5):1897-900. PMID:10803601

10.1.2 Carcinogen Classification

Carcinogen Classification
1, carcinogenic to humans. (L135)

10.1.3 Health Effects

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html

10.1.4 Exposure Routes

Oral (L4) ; inhalation (L4) ; dermal (L4)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html

10.1.5 Symptoms

Chronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)
A3: Aoki Y: Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters--what we have learned from Yusho disease. Environ Res. 2001 May;86(1):2-11. PMID:11386736

10.1.6 Toxicity Data

LD50: 1010 mg/kg (Oral, Rat) (T14) LD50: 880 mg/kg (Intraperitoneal, Mouse) (T14)
T14: Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.

10.1.7 Minimum Risk Level

Intermediate Oral: 0.03 ug/kg/day (L134)
L134: ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/mrls/

10.1.8 Treatment

There are no specific treatments for PCB poisoning, since it is not usually recognized until after substantial chronic exposure. Only preventing further exposure and treating the observed symptoms can be done. Acute inhalation can be treated by administering oxygen. (L4)
L4: ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp17.html

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Classification

14.1 ChemIDplus

14.2 UN GHS Classification

14.3 NORMAN Suspect List Exchange Classification

14.4 EPA DSSTox Classification

14.5 EPA Substance Registry Services Tree

14.6 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    2,2',3,4,4',5,6-Heptachlorobiphenyl
    https://comptox.epa.gov/dashboard/DTXSID8074235
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    1,1'-Biphenyl, 2,2',3,4,4',5,6-Heptachloro-
    http://www.nist.gov/srd/nist1a.cfm
  7. SpectraBase
    2,2',3,4,4',5,6-Heptachloro-1,1'-biphenyl
    https://spectrabase.com/spectrum/JinZZrPbIrm
  8. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  9. Springer Nature
  10. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
    2,2',3,4,4',5,6-Heptachlorobiphenyl
    http://www.t3db.ca/toxins/T3D0570
  11. Wikidata
    2,2',3,4,4',5,6-heptachlorobiphenyl
    https://www.wikidata.org/wiki/Q27276760
  12. PubChem
  13. GHS Classification (UNECE)
  14. EPA Substance Registry Services
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  16. PATENTSCOPE (WIPO)
  17. NCBI
CONTENTS