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trans-4-Hydroxycyclohexanecarboxylic acid

PubChem CID
151138
Structure
trans-4-Hydroxycyclohexanecarboxylic acid_small.png
trans-4-Hydroxycyclohexanecarboxylic acid_3D_Structure.png
Molecular Formula
Synonyms
  • trans-4-hydroxycyclohexanecarboxylic acid
  • 4-Hydroxycyclohexanecarboxylic acid
  • cis-4-Hydroxycyclohexanecarboxylic Acid
  • 3685-26-5
  • 17419-81-7
Molecular Weight
144.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
4-hydroxycyclohexanecarboxylic acid is a 4-hydroxy monocarboxylic acid that is cyclohexane substituted by a carboxy group at position 1 and a hydroxy group at position 4. It has a role as a human urinary metabolite. It is functionally related to a cyclohexanecarboxylic acid.
trans-4-Hydroxycyclohexanecarboxylic acid has been reported in Tsuga dumosa with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
trans-4-Hydroxycyclohexanecarboxylic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-hydroxycyclohexane-1-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C7H12O3/c8-6-3-1-5(2-4-6)7(9)10/h5-6,8H,1-4H2,(H,9,10)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1CC(CCC1C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H12O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

3685-26-5
3685-22-1

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4-HCHC
  • 4-hydroxycyclohexanecarboxylic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
144.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
144.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
144.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
125
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

Solid

3.2.2 Dissociation Constants

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

183.0 100

147.0 98.30

273.0 71.37

170.0 71.17

217.0 39.34

Thumbnail
Thumbnail
Notes
instrument=Leco Pegasus IV
2 of 5
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MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

183 100

147 98.30

273 71.37

170 71.17

217 39.34

Thumbnail
Thumbnail

4.2.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

95.05076 100

41.00352 34.90

44.99802 29.40

69.0341 27

93.03587 23.80

Thumbnail
Thumbnail
2 of 6
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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

143.07212 100

97.06627 3.30

125.06142 3.20

Thumbnail
Thumbnail

4.2.3 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
143.0713682
Instrument
Agilent qTOF 6545
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
20 eV
Top 5 Peaks

143.07193 100

97.06643 60.70

95.05084 29.70

125.06148 10.20

59.01442 7.60

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
143.0713682
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
negative
Collision Energy
HCD (NCE 20-30-40%)
Top 5 Peaks

143.0713 100

97.0659 5.50

125.06068 5.40

141.05559 2.30

Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Precautionary Statement Codes

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

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

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

9 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 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 Taxonomy

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

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 UN GHS Classification

13.5 NORMAN Suspect List Exchange Classification

13.6 EPA DSSTox Classification

13.7 LOTUS Tree

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    trans-4-Hydroxycyclohexanecarboxylic acid
    https://comptox.epa.gov/dashboard/DTXSID30190327
    4-Hydroxycyclohexanecarboxylic acid
    https://comptox.epa.gov/dashboard/DTXSID901015736
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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-Hydroxycyclohexanecarboxylic Acid (cis- and trans- mixture)
    https://echa.europa.eu/substance-information/-/substanceinfo/100.204.988
    4-Hydroxycyclohexanecarboxylic Acid (cis- and trans- mixture) (EC: 680-048-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/209926
  5. 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
    4-Hydroxycyclohexylcarboxylic acid
    http://www.hmdb.ca/metabolites/HMDB0001988
  6. ChEBI
  7. 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/
    trans-4-Hydroxycyclohexanecarboxylic acid
    https://www.wikidata.org/wiki/Q27161527
  8. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
    4-Hydroxycyclohexylcarboxylic acid
    https://foodb.ca/compounds/FDB022785
  9. 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
  10. 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
    cis-4-Hydroxycyclohexanecarboxylic acid
    http://www.nist.gov/srd/nist1a.cfm
  11. IUPAC Digitized pKa Dataset
    cyclohexanecarboxylic acid, 4-hydroxy-
    https://github.com/IUPAC/Dissociation-Constants
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. 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
  14. Natural Product Activity and Species Source (NPASS)
  15. Metabolomics Workbench
  16. NMRShiftDB
  17. Springer Nature
  18. 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/
  19. Wikidata
    4-Hydroxycyclohexylcarboxylic acid
    https://www.wikidata.org/wiki/Q27161527
  20. PubChem
  21. 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
    4-hydroxycyclohexanecarboxylic acid
    https://www.ncbi.nlm.nih.gov/mesh/67070042
  22. GHS Classification (UNECE)
  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. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  25. PATENTSCOPE (WIPO)
  26. NCBI
CONTENTS