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Vanillic Acid

PubChem CID
8468
Structure
Vanillic Acid_small.png
Vanillic Acid_3D_Structure.png
Vanillic Acid__Crystal_Structure.png
Molecular Formula
Synonyms
  • Vanillic acid
  • 121-34-6
  • 4-HYDROXY-3-METHOXYBENZOIC ACID
  • Acide vanillique
  • p-Vanillic acid
Molecular Weight
168.15 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate.
A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).
Vanillic acid has been reported in Camellia sinensis, Paeonia obovata, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Vanillic Acid.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

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

2.2 Molecular Formula

C8H8O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

121-34-6

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 FEMA Number

2.3.9 HMDB ID

2.3.10 JECFA Number

959

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4 Hydroxy 3 methoxybenzoic Acid
  • 4-Hydroxy-3-methoxybenzoic Acid
  • Acid, 4-Hydroxy-3-methoxybenzoic
  • Acid, p-Hydroxy-m-methoxy-benzoic
  • Acid, Vanillic
  • p Hydroxy m methoxy benzoic Acid
  • p-Hydroxy-m-methoxy-benzoic Acid
  • Vanillic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
168.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.4
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
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
168.04225873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
168.04225873 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
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
168
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 odorless solid; [Merck Index] White to beige powder; [Acros Organics MSDS]
Solid
White to beige powder or needle; vanilla like odour

3.2.2 Melting Point

211.5 °C
PhysProp
211.5 °C

3.2.3 Solubility

1500 mg/L (at 14 °C)
YALKOWSKY,SH & DANNENFELSER,RM (1992)
1.5 mg/mL at 14 °C
YALKOWSKY,SH & DANNENFELSER,RM (1992)
slightly soluble in water; soluble in organic solvents
soluble (in ethanol)

3.2.4 Vapor Pressure

0.0000171 [mmHg]

3.2.5 LogP

1.43
HANSCH,C ET AL. (1995)
1.43
HANSCH,C ET AL. (1995)

3.2.6 LogS

-2.05
ADME Research, USCD

3.2.7 Dissociation Constants

pKa
4.51 (at 25 °C)
SERJEANT,EP & DEMPSEY,B (1979)

3.2.8 Collision Cross Section

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

3.2.9 Kovats Retention Index

Standard non-polar
1620
Semi-standard non-polar
1592 , 1566 , 1566 , 1608 , 1613.8 , 1627.8 , 1570

3.3 Chemical Classes

Biological Agents -> Plant Oils and Extracts

3.3.1 Drugs

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

3.3.2 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

3.3.3 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
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Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
6.90
Shifts [ppm]:Intensity
7.44:12.86, 7.52:22.87, 7.52:24.74, 6.93:21.61, 3.90:100.00, 7.45:11.34, 6.94:23.35, 7.44:12.06, 7.46:12.23
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Spectra ID
Instrument Type
Bruker
Solvent
DMSO
Shifts [ppm]:Intensity
7.52:1.89, 3.90:15.00, 7.45:1.01, 7.46:1.15, 6.94:2.10, 7.51:2.03, 7.44:1.11, 7.44:1.22, 6.92:2.00
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4.1.2 13C NMR Spectra

1 of 4
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Spectra ID
Frequency
500 MHz
Solvent
DMSO
Shifts [ppm]
149.46, 150.65, 125.82, 177.86, 58.56, 131.29, 117.52, 115.81
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Spectra ID
Instrument Type
Bruker
Solvent
DMSO
Shifts [ppm]:Intensity
177.86:3.07, 117.52:14.03, 150.65:4.03, 125.82:14.71, 149.46:4.10, 58.56:12.75, 115.81:15.00, 131.30:5.10
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
7.45:125.80:0.24, 6.96:117.52:0.25, 7.52:115.79:0.49, 3.90:58.45:1.00
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 11
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

168.0 99.99

153.0 46.24

97.0 17.39

169.0 14.34

151.0 13.78

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Notes
instrument=HITACHI M-80
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

297.0 1

267.0 0.94

223.0 0.89

253.0 0.61

126.0 0.59

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4.3.2 MS-MS

1 of 7
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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

91.019 100

108.02199 92.40

152.01335 24.10

65.00257 23.50

123.04464 12.60

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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

108.0216 100

152.0119 37.04

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4.3.3 LC-MS

1 of 13
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Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
154.8 sec
Top 5 Peaks

167.035 999

357.0583 333

289.0703 186

541.0648 157

152.0109 120

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License
CC BY-NC-SA
2 of 13
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
154.8 sec
Precursor m/z
167.1
Precursor Adduct
[M-H]-
Top 5 Peaks

108.0216 999

152.0119 370

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License
CC BY-NC-SA

4.3.4 Other MS

1 of 4
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Authors
NARA WOMEN'S UNIVERSITY
Instrument
HITACHI M-80
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

168 999

153 462

97 174

169 143

151 138

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License
CC BY-NC-SA
2 of 4
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MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
169.05
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

125.059685 100

93.033371 14.45

151.039078 7.35

65.038361 3.12

110.036224 2.15

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4.4 UV Spectra

4.4.1 UV-VIS Spectra

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

4.5.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A12074
Lot Number
10191486
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5.2 ATR-IR Spectra

1 of 2
Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A12074
Lot Number
10191486
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

7.2 Biomarker Information

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Astringent, Vanilla

8.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
FEMA Number
3988
GRAS Number
20
JECFA Flavor Number
959

8.4 Associated Foods

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

1 of 3
Evaluation Year
2001
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
2 of 3
Chemical Name
4-HYDROXY-m-ANISIC ACID
Evaluation Year
2001
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
3 of 3
Chemical Name
VANILLIC ACID
Evaluation Year
2001
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Cellular Locations

Cytoplasm

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as flavoring agent or adjuvant; [FDA]

10.1.1 Use Classification

Food additives -> Flavoring Agents
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzoic acid, 4-hydroxy-3-methoxy-: ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 72.4% (97 of 134) of all reports. Pictograms displayed are for 27.6% (37 of 134) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (27.6%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (27.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (26.9%): 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 134 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 97 of 134 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 7 notifications provided by 37 of 134 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.

11.1.2 Hazard Classes and Categories

Skin Irrit. 2 (27.6%)

Eye Irrit. 2A (27.6%)

STOT SE 3 (26.9%)

11.1.3 Hazards Summary

Causes other liver changes, effects on other transferases, and inflammatory effects in acute intraperitoneal studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] An irritant; [Acros Organics MSDS] See Vanillin.

11.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzoic acid, 4-hydroxy-3-methoxy-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Benzoic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard

11.3 Other Safety Information

Chemical Assessment
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

12 Toxicity

12.1 Toxicological Information

12.1.1 Acute Effects

13 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

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.2 Chemical-Target Interactions

16.3 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

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

19 Classification

19.1 MeSH Tree

19.2 ChEBI Ontology

19.3 ChemIDplus

19.4 ChEMBL Target Tree

19.5 UN GHS Classification

19.6 EPA CPDat Classification

19.7 NORMAN Suspect List Exchange Classification

19.8 CCSBase Classification

19.9 EPA DSSTox Classification

19.10 The Natural Products Atlas Classification

19.11 EPA TSCA and CDR Classification

19.12 LOTUS Tree

19.13 EPA Substance Registry Services Tree

19.14 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
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    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
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    https://www.drugbank.ca/legal/terms_of_use
  5. DTP/NCI
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    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
    Benzoic acid, 4-hydroxy-3-methoxy-
    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
  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. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  11. 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/
  12. BindingDB
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    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  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. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. ChEBI
  16. 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/
  17. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  18. ChEMBL
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    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
  19. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  20. Crystallography Open Database (COD)
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    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/
  21. 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
  22. IUPAC Digitized pKa Dataset
    benzoic acid, 4-hydroxy-3-methoxy-
    https://github.com/IUPAC/Dissociation-Constants
  23. EPA Chemical and Products Database (CPDat)
  24. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
  25. EU Food Improvement Agents
  26. 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
  27. 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/
    Vanillic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. Flavor and Extract Manufacturers Association (FEMA)
  29. 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
  30. 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
  31. 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
  32. SpectraBase
    4-Hydroxy-3-methoxy-benzoic acid
    https://spectrabase.com/spectrum/GZ8saVhVJFw
    4-Hydroxy-3-methoxybenzoic acid
    https://spectrabase.com/spectrum/4edudAOc6NN
    4-Hydroxy-3-methoxybenzoic acid
    https://spectrabase.com/spectrum/IlJndTIjLQU
  33. Japan Chemical Substance Dictionary (Nikkaji)
  34. 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
  35. KNApSAcK Species-Metabolite Database
  36. Natural Product Activity and Species Source (NPASS)
  37. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  38. MassBank Europe
  39. Metabolomics Workbench
  40. NMRShiftDB
  41. Springer Nature
  42. The Cambridge Structural Database
  43. 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/
  44. Wikidata
  45. Wikipedia
  46. Wiley
  47. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  48. PubChem
  49. GHS Classification (UNECE)
  50. The Natural Products Atlas
    LICENSE
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    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  51. EPA Substance Registry Services
  52. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  53. PATENTSCOPE (WIPO)
  54. NCBI
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