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Triphenylethylene

PubChem CID
6025
Structure
Triphenylethylene_small.png
Triphenylethylene_3D_Structure.png
Molecular Formula
Synonyms
  • TRIPHENYLETHYLENE
  • 58-72-0
  • Triphenylethene
  • Ethylene, triphenyl-
  • 1,1,2-Triphenylethylene
Molecular Weight
256.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-02-01
Description
Triphenylethylene is a stilbenoid.
Triphenylethylene is the core chemical structure of a number of related anti-estrogen compounds. The triphenylethylene antiestrogens, which include idoxifene, toremifene, chlorotrianisene, raloxifene and tamoxifen, act at the level of the estrogen receptor, triggering inhibition or stimulation of estrogen-dependent gene transcription and cellular physiology. Triphenylethylenes were initially developed for the treatment of estrogen-dependent breast cancers. Selective estrogen receptor modulators (SERMs) such as raloxifene and tamoxifen represent triphenylethylene derivatives that affect transcriptional regulation through modulation of specific alpha and beta estrogen receptors that are differentially expressed in various normal and neoplastic tissues. (NCI04)

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Triphenylethylene.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2-diphenylethenylbenzene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MKYQPGPNVYRMHI-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H16
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

58-72-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

triphenylethylene

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
256.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
6.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
256.125200510 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
256.125200510 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
276
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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 Experimental Properties

3.2.1 Physical Description

White crystalline solid; [Sigma-Aldrich MSDS]

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Aromatic Hydrocarbons

3.4.1 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 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Catalog Number
7586
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
T82805
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Varian HA-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Unknown
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

256 99.99

178 50.50

241 23.90

165 23.60

257 21.30

Thumbnail
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License
CC BY-NC-SA
2 of 6
View All
NIST Number
235652
Library
Main library
Total Peaks
176
m/z Top Peak
256
m/z 2nd Highest
178
m/z 3rd Highest
179
Thumbnail
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4.2.2 Other MS

Authors
SASAKI S, TOYOHASHI UNIV. OF TECH.
Instrument
Unknown
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Top 5 Peaks

256 999

178 505

241 239

165 236

257 213

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 UV Spectra

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: MELT
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Catalog Number
7586
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Film from methylene chloride on CsI
Source of Sample
H.-H. Hoerhold, Friedrich-Schiller-Universitaet, Jena
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.4.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
T82805
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
T82805
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Estrogen Antagonists
Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H400 (97.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (97.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

Acute Tox. 4 (100%)

Eye Irrit. 2 (100%)

Aquatic Acute 1 (97.6%)

Aquatic Chronic 1 (97.6%)

9.1.3 Hazards Summary

A skin and strong eye irritant; Harmful by ingestion; May cause allergic reactions in sensitive individuals, based on QSAR modeling; Reproductive effects observed in experimental animals; [Sigma-Aldrich MSDS] See Triphenylmethane. See 1,1-Diphenylethylene and 1,2-Diphenylethylene.

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-
New Zealand EPA Inventory of Chemical Status
Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-: Does not have an individual approval but may be used under an appropriate group standard

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Wiley References

10.6 Chemical Co-Occurrences in Literature

10.7 Chemical-Gene Co-Occurrences in Literature

10.8 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 ChEBI Ontology

14.4 ChemIDplus

14.5 UN GHS Classification

14.6 NORMAN Suspect List Exchange Classification

14.7 EPA DSSTox Classification

14.8 EPA TSCA and CDR Classification

14.9 EPA Substance Registry Services Tree

14.10 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemicals under the TSCA
    Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. 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
  9. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. ChEBI
  11. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  14. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  15. Human Metabolome Database (HMDB)
    LICENSE
    HMDB 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 (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  18. MassBank Europe
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. 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
    Benzene, 1,1',1''-(1-ethenyl-2-ylidene)tris-
    http://www.nist.gov/srd/nist1a.cfm
  21. SpectraBase
    BENZENE, 1,1',1''-(1-ETHENYL-2-YLIDENE)TRIS-
    https://spectrabase.com/spectrum/HilWY8ILARQ
    Benzene, 1,1'',1''''-(1-ethenyl-2-ylidene)tris-
    https://spectrabase.com/spectrum/KDrxj0giNy5
    Poly(1,4-phenylene-1,2-diphenylethenylene)
    https://spectrabase.com/spectrum/4osVIrg0xiu
  22. Metabolomics Workbench
  23. 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/
  24. Springer Nature
  25. SpringerMaterials
  26. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  27. Wikidata
  28. Wikipedia
  29. Wiley
  30. PubChem
  31. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  32. GHS Classification (UNECE)
  33. EPA Substance Registry Services
  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
CONTENTS