An official website of the United States government

3-Methoxy-4-hydroxymandelate

PubChem CID
1245
Structure
3-Methoxy-4-hydroxymandelate_small.png
3-Methoxy-4-hydroxymandelate_3D_Structure.png
Molecular Formula
Synonyms
  • Vanillylmandelic acid
  • 55-10-7
  • dl-4-Hydroxy-3-methoxymandelic acid
  • 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
  • 2394-20-9
Molecular Weight
198.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Vanillylmandelic acid is an aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid. It has a role as a human metabolite. It is an aromatic ether, a 2-hydroxy monocarboxylic acid and a member of phenols. It is functionally related to a mandelic acid. It is a conjugate acid of a vanillylmandelate.
Vanillylmandelic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Vanillylmandelic acid has been reported in Homo sapiens, Pogostemon cablin, and Phaseolus vulgaris with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-Methoxy-4-hydroxymandelate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

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

2.2 Molecular Formula

C9H10O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2394-20-9

2.3.2 Deprecated CAS

2394-20-9

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 FEMA Number

2.3.9 JECFA Number

2020

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4 Hydroxy 3 Methoxymandelic Acid
  • 4-Hydroxy-3-Methoxymandelic Acid
  • Acid, 4-Hydroxy-3-Methoxymandelic
  • Acid, Methoxyhydroxymandelic
  • Acid, Vanillylmandelic
  • Acid, Vanilmandelic
  • Methoxyhydroxymandelic Acid
  • Vanillylmandelic Acid
  • Vanilmandelic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
198.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.2
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
5
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
198.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
198.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
87 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
205
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
1
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

Pale yellow powder; Sweet vanilla aroma

3.2.2 Solubility

Sparingly soluble in water
Sparingly soluble (in ethanol)

3.2.3 Collision Cross Section

143.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

140.9 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

133.3 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

130.6 Ų [M-H]-
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 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
148806
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 9
View All
Authors
Tsujimoto Y, Tsugawa H, Bamba T, Fukusaki E, engineering department, Osaka Univ.
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
CP-SIL 8 CB LOW BLEED/MS
Retention Time
718.418 sec
Top 5 Peaks

297 999

298 306

147 256

299 124

194 106

Thumbnail
Thumbnail
License
CC BY-SA
2 of 9
View All
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

297 100

147 38.64

298 26.73

194 14.71

193 12.31

Thumbnail
Thumbnail

4.2.2 MS-MS

NIST Number
1051398
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
197.0455
Total Peaks
6
m/z Top Peak
138
m/z 2nd Highest
153
m/z 3rd Highest
137.1
Thumbnail
Thumbnail

4.2.3 LC-MS

1 of 12
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 V
Precursor m/z
197
Precursor Adduct
[M-H]-
Top 5 Peaks

197.2 999

138 35

152.7 8

137 4

120.9 1

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 12
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
20 V
Precursor m/z
197
Precursor Adduct
[M-H]-
Top 5 Peaks

138 999

137.3 580

197.2 266

152.9 23

196.7 16

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.4 Other MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
197.17
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
10
Top 5 Peaks

197 100

196 5.84

Thumbnail
Thumbnail
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
197.17
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
30
Top 5 Peaks

137 100

138 15.82

Thumbnail
Thumbnail

4.3 UV Spectra

4.3.1 UV-VIS Spectra

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

4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
4542
Lot Number
902371
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
H0268
Lot Number
GB01 -LTFT
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
4542
Lot Number
902371
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
H0268
Lot Number
GB01 -LTFT
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents

7.2 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
FEMA Number
4660
GRAS Number
24
JECFA Flavor Number
2020

7.3 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
Evaluation Year
2010
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Pharmacology and Biochemistry

8.1 Biochemical Reactions

8.2 Transformations

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Food additives -> Flavoring Agents
Flavoring Agents -> JECFA Flavorings Index

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzeneacetic acid, .alpha.,4-dihydroxy-3-methoxy-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

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

H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (97.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (95%): 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 40 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.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (97.5%)

Eye Irrit. 2 (97.5%)

STOT SE 3 (95%)

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Benzeneacetic acid, .alpha.,4-dihydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

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

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 UN GHS Classification

17.5 NORMAN Suspect List Exchange Classification

17.6 CCSBase Classification

17.7 EPA DSSTox Classification

17.8 EPA TSCA and CDR Classification

17.9 LOTUS Tree

17.10 EPA Substance Registry Services Tree

17.11 MolGenie Organic Chemistry Ontology

18 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 Chemicals under the TSCA
    Benzeneacetic acid, .alpha.,4-dihydroxy-3-methoxy-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  7. 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/
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. 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/
    Vanillylmandelic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  10. ChEBI
  11. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  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/
  13. 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
  14. 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
  15. 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
  16. EU Food Improvement Agents
  17. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  18. FDA Substances Added to Food
    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
  19. Flavor and Extract Manufacturers Association (FEMA)
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. 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
  22. KNApSAcK Species-Metabolite Database
  23. Natural Product Activity and Species Source (NPASS)
    2-Hydroxy-2-(4-Hydroxy-3-Methoxyphenyl)Acetic Acid
    https://bidd.group/NPASS/compound.php?compoundID=NPC307006
  24. MassBank Europe
  25. 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
  26. 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
    Mandelic acid, 4-hydroxy-3-methoxy-
    http://www.nist.gov/srd/nist1a.cfm
  27. SpectraBase
    4-HYDROXY-3-METHOXYMANDELIC ACID
    https://spectrabase.com/spectrum/E4TR0NGv6DP
    D,L-3-Methoxy-4-hydroxymandelic acid
    https://spectrabase.com/spectrum/EZrweqdNtGB
    D,L-4-Hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/KcfaA97G3dd
    DL-4-HYDROXY-3-METHOXYMANDELIC ACID
    https://spectrabase.com/spectrum/2LHeslpqitG
    4-HYDROXY-3-METHOXYMANDELIC ACID
    https://spectrabase.com/spectrum/GDFxTIdDuGr
    4-hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/EY6lGdoJZfu
    D,L-3-Methoxy-4-hydroxymandelic acid
    https://spectrabase.com/spectrum/2eoAZtclj5a
    D,L-4-Hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/4JK4FUdET8v
    DL-4-HYDROXY-3-METHOXYMANDELIC ACID
    https://spectrabase.com/spectrum/HIghIjVUIT8
    4-Hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/A9ADOFLnvoW
    DL-4-hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/JkMRD4qgFcq
    DL-4-hydroxy-3-methoxymandelic acid
    https://spectrabase.com/spectrum/4SkiJirl9Nl
  28. Metabolomics Workbench
    2-Hydroxy-2-(4-Hydroxy-3-Methoxyphenyl)Acetic Acid
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=123038
  29. Springer Nature
  30. 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/
  31. Wikidata
    DL-4-Hydroxy-3-methoxymandelic acid
    https://www.wikidata.org/wiki/Q72484825
  32. Wikipedia
  33. Wiley
  34. 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
  35. PubChem
  36. GHS Classification (UNECE)
  37. EPA Substance Registry Services
  38. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  39. PATENTSCOPE (WIPO)
CONTENTS