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1,3,5-Benzenetricarboxylic acid

PubChem CID
11138
Structure
1,3,5-Benzenetricarboxylic acid_small.png
1,3,5-Benzenetricarboxylic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Trimesic acid
  • 554-95-0
  • benzene-1,3,5-tricarboxylic acid
  • 1,3,5-BENZENETRICARBOXYLIC ACID
  • Trimesinic acid
Molecular Weight
210.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
Benzene-1,3,5-tricarboxylic acid is a tricarboxylic acid that consists of benzene substituted by carboxy groups at positions 1, 3 and 5. It is a tricarboxylic acid and a member of benzoic acids. It is a conjugate acid of a benzene-1,3,5-tricarboxylate(1-).
1,3,5-Benzenetricarboxylic acid has been reported in Phaseolus vulgaris with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,3,5-Benzenetricarboxylic acid.png

1.2 3D Conformer

1.3 Crystal Structures

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzene-1,3,5-tricarboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=C(C=C(C=C1C(=O)O)C(=O)O)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H6O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

554-95-0

2.3.2 Deprecated CAS

1585941-71-4, 2634727-14-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 Metabolomics Workbench ID

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

  • 1,3,5-benzenetricarboxylate
  • 1,3,5-benzenetricarboxylic acid
  • benzene-1,3,5-carboxylic acid
  • trimesic acid
  • trimesic acid, monosodium salt
  • trimesic acid, trisodium salt

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
210.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
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
210.01643791 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
210.01643791 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
112 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
237
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 to cream crystalline powder; [Alfa Aesar MSDS]

3.2.2 Vapor Pressure

0.00000003 [mmHg]

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Organic Acids

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 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
B4406
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
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
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 7
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

193.0 99.99

210.0 78.95

65.0 42.08

81.0 33.85

75.0 33.50

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Notes
instrument=HITACHI M-80
2 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

193 99.99

210 78.95

65 42.08

81 33.85

75 33.50

Thumbnail
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License
CC BY-NC-SA

4.2.2 Other MS

Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI M-80
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

193 999

210 790

65 421

81 339

75 335

Thumbnail
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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Amoco Chemicals Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
KBr WAFER
Source of Sample
Polysciences, Inc., Warrington, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Source of Sample
Aldrich
Catalog Number
412279
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
482749
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Instrument Name
Bio-Rad FTS 175C with Raman accessory
Technique
FT-Raman
Source of Sample
Amoco Chemicals Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
1,3,5-Benzenetricarboxylic acid: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 65% (91 of 140) of all reports. Pictograms displayed are for 35% (49 of 140) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (35%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (35%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (34.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, 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 140 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 91 of 140 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 8 notifications provided by 49 of 140 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.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (35%)

Eye Irrit. 2A (35%)

STOT SE 3 (34.3%)

8.1.3 Hazards Summary

A skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS]

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,3,5-Benzenetricarboxylic acid
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,3,5-Benzenetricarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Thieme References

9.5 Wiley References

9.6 Chemical Co-Occurrences in Literature

9.7 Chemical-Gene Co-Occurrences in Literature

9.8 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Protein Bound 3D Structures

11.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

11.2 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 ChEMBL Target Tree

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 LOTUS Tree

14.10 EPA Substance Registry Services Tree

14.11 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  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. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. 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
  6. EPA Chemicals under the TSCA
    1,3,5-Benzenetricarboxylic acid
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. 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
    Benzene-1,3,5-tricarboxylic acid
    https://chem.echa.europa.eu/100.008.253
  9. 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
  10. 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/
  11. ChEBI
  12. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    1,3,5-Benzenetricarboxylic acid
    https://www.wikidata.org/wiki/Q981152
  13. 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
  14. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  15. Therapeutic Target Database (TTD)
  16. 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
    1,3,5-Benzenetricarboxylic acid
    https://haz-map.com/Agents/19225
  17. 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
  18. 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
  19. 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
    1,3,5-Benzenetricarboxylic acid
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
    BENZENE-1,3,5-TRICARBOXYLIC ACID
    https://spectrabase.com/spectrum/8cwk8V0og2N
    1,3,5-Benzenetricarboxylic acid
    https://spectrabase.com/spectrum/LcJeLuUAMh3
    1,3,5-BENZENETRICARBOXYLIC ACID
    https://spectrabase.com/spectrum/DGSdezXkdpo
    1,3,5-Benzenetricarboxylic acid
    https://spectrabase.com/spectrum/I5gAHnGDwvu
    1,3,5-BENZENETRICARBOXYLIC ACID
    https://spectrabase.com/spectrum/7llzfgY7lye
    1,3,5-BENZENETRICARBOXYLIC ACID
    https://spectrabase.com/spectrum/9stbsQf9xgB
  21. Japan Chemical Substance Dictionary (Nikkaji)
  22. KNApSAcK Species-Metabolite Database
  23. MassBank Europe
  24. Metabolomics Workbench
  25. NMRShiftDB
  26. 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/
    1,3,5-Benzenetricarboxylic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. Protein Data Bank in Europe (PDBe)
  28. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  29. Springer Nature
  30. SpringerMaterials
  31. 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/
  32. Wikidata
    1,3,5-benzenetricarboxylic acid
    https://www.wikidata.org/wiki/Q981152
  33. Wikipedia
  34. Wiley
  35. PubChem
  36. 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
  37. GHS Classification (UNECE)
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
CONTENTS