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Dihydroferulic Acid

PubChem CID
14340
Structure
Dihydroferulic Acid_small.png
Dihydroferulic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • 1135-23-5
  • 3-(4-Hydroxy-3-methoxyphenyl)propionic acid
  • 3-(4-Hydroxy-3-methoxyphenyl)propanoic acid
  • dihydroferulic acid
  • Hydroferulic acid
Molecular Weight
196.20 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
Dihydroferulic acid is a monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group. It has a role as a human xenobiotic metabolite, a plant metabolite, a mouse metabolite and an antioxidant. It is a monocarboxylic acid, a phenylpropanoid and a member of guaiacols. It is functionally related to a propionic acid. It is a conjugate acid of a dihydroferulate.
3-(4-Hydroxy-3-methoxyphenyl)propionic acid has been reported in Stellaria dichotoma, Melicope semecarpifolia, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dihydroferulic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

COC1=C(C=CC(=C1)CCC(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H12O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

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 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

dihydroferulic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
196.20 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.7
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
196.07355886 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
196.07355886 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
193
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)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

NIST Number
136441
Library
Main library
Total Peaks
48
m/z Top Peak
137
m/z 2nd Highest
196
m/z 3rd Highest
77
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4.2.2 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
195.0662841796875
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
negative
Collision Energy
35HCD
Top 5 Peaks

136.051845 100

195.065608 50.36

135.044083 19.73

59.012504 10.78

119.049042 8.21

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2 of 3
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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
195.0662841796875
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
negative
Collision Energy
45HCD
Top 5 Peaks

136.051824 100

135.044051 15.74

121.028343 14.17

119.049042 10.81

195.065698 10.25

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4.2.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
M-H
Precursor m/z
195.066
Instrument
Orbitrap
Ionization Mode
negative
Retention Time
CCS:
Top 5 Peaks

136.053421 100

151.07695 81.78

135.045654 62.84

123.045731 19.61

177.056137 18.27

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2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
2M-2H+Na
Precursor m/z
413.122
Instrument
Orbitrap
Ionization Mode
negative
Retention Time
CCS:
Top 5 Peaks

217.048569 100

195.066605 50.35

202.025131 22.38

339.991486 9.64

283.841858 3.55

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4.3 UV Spectra

4.3.1 UV-VIS Spectra

1 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

4.4.1 FTIR Spectra

Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr0
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, A Johnson Matthey Company
Catalog Number
A12069
Lot Number
10122342
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, A Johnson Matthey Company
Catalog Number
A12069
Lot Number
10122342
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, A Johnson Matthey Company
Catalog Number
A12069
Lot Number
10122342
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Dihydroferulic acid has known human metabolites that include 3-[3-Methoxy-4-(sulfooxy)phenyl]propanoic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Biochemical Reactions

7.3 Transformations

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (88.4%): Harmful if swallowed [Warning Acute toxicity, oral]

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

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

H335 (97.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, 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 43 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.

8.1.2 Hazard Classes and Categories

Acute Tox. 4 (88.4%)

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

STOT SE 3 (97.7%)

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 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 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 Protein Bound 3D Structures

12.2 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

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

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 ChEMBL Target Tree

15.5 UN GHS Classification

15.6 NORMAN Suspect List Exchange Classification

15.7 EPA DSSTox Classification

15.8 LOTUS Tree

15.9 MolGenie Organic Chemistry Ontology

16 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
    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
  5. 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
  6. 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
  7. ChEBI
  8. 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/
    3-(4-Hydroxy-3-methoxyphenyl)propionic acid
    https://www.wikidata.org/wiki/Q10395564
  9. 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
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. KNApSAcK Species-Metabolite Database
  12. Natural Product Activity and Species Source (NPASS)
  13. 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
  14. Metabolomics Workbench
  15. 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
    .beta.-(4-Hydroxy-3-methoxyphenyl)propionic acid
    http://www.nist.gov/srd/nist1a.cfm
  16. 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/
    Dihydroferulic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. SpectraBase
    4-hydroxy-3-methoxyhydrocinnamic acid
    https://spectrabase.com/spectrum/62r6aViqzze
    4-hydroxy-3-methoxyhydrocinnamic acid
    https://spectrabase.com/spectrum/3WDt5JSb0Ha
    3-(3-METHOXY-4-HYDROXYPHENYL)-PROPIONIC-ACID
    https://spectrabase.com/spectrum/86BNNp4DTFP
    3-(4-Hydroxy-3-methoxyphenyl)propionic acid
    https://spectrabase.com/spectrum/1lqBBSvKvEW
    3-(4-Hydroxy-3-methoxyphenyl)propionic acid
    https://spectrabase.com/spectrum/HsMwf46vs1u
    3-(4-Hydroxy-3-methoxyphenyl)propionic acid
    https://spectrabase.com/spectrum/4jrwNKi6ziB
  18. Springer Nature
  19. Wikidata
  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
  22. GHS Classification (UNECE)
  23. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  24. PATENTSCOPE (WIPO)
CONTENTS