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Arachidic Acid

PubChem CID
10467
Structure
Arachidic Acid_small.png
Arachidic Acid__Crystal_Structure.png
Molecular Formula
Synonyms
  • Arachidic acid
  • Icosanoic acid
  • EICOSANOIC ACID
  • 506-30-9
  • Arachic acid
Molecular Weight
312.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-02-01
Description
Icosanoic acid is a C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of an icosanoate.
Arachidic acid has been reported in Calodendrum capense, Amaranthus hybridus, and other organisms with data available.
Arachidic Acid is a saturated long-chain fatty acid with a 20-carbon backbone. Arachidic acid is found naturally as a minor component of peanut oil.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Arachidic Acid.png

1.2 3D Status

Conformer generation is disallowed since too flexible

1.3 Crystal Structures

CCDC Number
Associated Article
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

icosanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCCCCCCCCCCCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H40O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

506-30-9

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 HMDB ID

2.3.9 KEGG ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • arachidic acid
  • arachidic acid, ammonium salt
  • arachidic acid, barium salt
  • arachidic acid, calcium salt
  • arachidic acid, magnesium salt
  • arachidic acid, potassium salt
  • arachidic acid, sodium salt
  • zinc arachidate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
312.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
8.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
18
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
312.302830514 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
312.302830514 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
226
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

Other Solid; Liquid
Solid; [Merck Index] White crystalline flakes; [Alfa Aesar MSDS]
Solid

3.2.2 Boiling Point

328.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.3 Melting Point

75.4 °C

3.2.4 LogP

9.29
SANGSTER (1993)

3.2.5 Ionization Efficiency

Ionization mode
Positive
logIE
1.25
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)
Reference
DOI:

3.2.6 Collision Cross Section

184.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
183.41 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

186.36 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

199.97 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

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

185 Ų [M-H]-

185.9 Ų [M-H]-

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.2.7 Kovats Retention Index

Standard non-polar
2380 , 2366 , 2359
Semi-standard non-polar
2365.3 , 2380 , 2359 , 2359 , 377.8

3.3 Chemical Classes

Biological Agents -> Fatty Acids and Fats

3.3.1 Cosmetics

Cosmetic ingredients (Arachidic Acid) -> CIR (Cosmetic Ingredient Review)
Emulsifying
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.3.2 Lipids

Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
CDCl3
pH
7.00
Shifts [ppm]:Intensity
2.34:6.97, 0.88:9.49, 2.36:4.04, 1.60:0.90, 1.61:2.60, 1.63:3.52, 1.25:100.00, 1.64:2.56, 2.33:3.95, 0.89:4.88, 1.66:1.08, 0.86:4.42, 1.29:8.72
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Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
2.35:25.00, 1.26:1000.00, 0.88:43.00
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4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
29.10:154.00, 31.96:127.00, 24.72:103.00, 29.40:247.00, 34.03:99.00, 29.48:253.00, 29.72:1000.00, 14.11:86.00, 22.71:123.00, 29.28:192.00, 179.83:164.00
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Source of Sample
Lachat Chemicals, Inc., Chicago Heights, Illinois
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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
100%_DMSO
pH
7.00
Shifts [ppm] (F2:F1):Intensity
2.18:33.55:0.08, 1.24:28.88:1.00, 1.23:31.03:0.07, 1.26:22.26:0.03, 1.44:28.91:0.10, 0.83:13.78:0.04, 1.48:24.25:0.06
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 17
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

43.0 99.99

73.0 87

57.0 81

60.0 79.80

41.0 67.70

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Notes
instrument=HITACHI M-80B
2 of 17
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Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

117.0 100

132.0 52.65

129.0 48.25

145.0 29.83

131.0 14.91

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

4.3.2 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

57.0 100

56.0 44.44

70.0 39.74

71.0 36.65

55.0 23.45

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 6
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

56.0 100

57.0 69.52

68.0 34.63

55.0 31.99

144.0 27.41

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

4.3.3 LC-MS

1 of 6
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Retention Time
0.164 min
Precursor m/z
311.2956
Precursor Adduct
[M-H]-
Top 5 Peaks

311.2965 999

293.2847 16

294.2872 3

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License
CC BY
2 of 6
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40 eV
Fragmentation Mode
CID
Retention Time
0.148 min
Precursor m/z
311.2956
Precursor Adduct
[M-H]-
Top 5 Peaks

311.2899 999

119.0476 692

191.9993 506

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License
CC BY

4.3.4 Other MS

1 of 4
View All
Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

43 999

73 870

57 810

60 798

41 677

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License
CC BY-NC-SA
2 of 4
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
311.313
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

311.317657 100

312.325165 8.78

174.965546 7.82

96.737442 0.98

146.965622 0.70

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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Instrument Name
PERKIN-ELMER 1710
Technique
NUJOL MULL
Source of Sample
Deva Biotech
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
CAPILLARY CELL: MELT
Source of Sample
Lachat Chemicals, Inc., Chicago Heights, Illinois
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 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
E0006
Lot Number
XYPMK-SS
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
E231
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 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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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
E0006
Lot Number
XYPMK-SS
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

Placenta

8.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane

8.2 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Arachidic Acid
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
Fatty acid present in peanut oil, vegetable oil, fish oil, etc.; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

9.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green circle Green circle - The chemical has been verified to be of low concern
Cosmetics -> Emulsifying
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

9.1.2 Industry Uses

  • Lubricants and lubricant additives
  • Adhesives and sealant chemicals
  • Intermediates
  • Intermediate
  • Fuel
  • Finishing agents
  • Agricultural chemicals (non-pesticidal)
  • Softener and conditioner
  • Lubricating agent
  • Surface active agents

9.1.3 Consumer Uses

  • Adhesives and sealant chemicals
  • Not Known or Reasonably Ascertainable
  • Agricultural chemicals (non-pesticidal)
  • Softener and conditioner

9.1.4 Household Products

Household & Commercial/Institutional Products

Information on 20 consumer products that contain Arachidic acid in the following categories is provided:

• Personal Care

9.2 U.S. Production

Aggregated Product Volume

2019: 1,000,000 - <10,000,000 lb

2018: 1,000,000 - <10,000,000 lb

2017: 1,000,000 - <10,000,000 lb

2016: 1,000,000 - <10,000,000 lb

9.3 General Manufacturing Information

Industry Processing Sectors
  • Food, beverage, and tobacco product manufacturing
  • Mining (except Oil and Gas) and support activities
  • Miscellaneous Manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Other (requires additional information)
  • Paper Manufacturing
  • Plastics Product Manufacturing
  • Soap, Cleaning Compound, and Toilet Preparation Manufacturing
EPA TSCA Commercial Activity Status
Eicosanoic acid: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 89.1% (238 of 267) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 10.9% (29 of 267) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (89.1%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (89.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (56.6%): 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 267 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 29 of 267 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 5 notifications provided by 238 of 267 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.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (89.1%)

Eye Irrit. 2 (89.1%)

STOT SE 3 (56.6%)

10.1.3 EPA Safer Chemical

Chemical: Eicosanoic acid

Green circle Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.

10.1.4 Hazards Summary

n-Alkyl carboxylic acids: Category members demonstrate low acute oral, dermal, and inhalation toxicity; Low potential to cause skin sensitization; Low repeated-dose toxicity; Low or no reproductive or developmental toxicity; [EPA ChAMP: Hazard Characterization] A skin and strong eye irritant; [Alfa Aesar MSDS]

10.2 Regulatory Information

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

10.3 Other Safety Information

Chemical Assessment

IMAP assessments - Eicosanoic acid: Environment tier I assessment

IMAP assessments - Eicosanoic acid: Human health tier I assessment

11 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 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

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Wiley References

12.5 Nature Journal 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 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 LIPID MAPS Classification

17.5 KEGG: Metabolite

17.6 KEGG: Lipid

17.7 KEGG: Phytochemical Compounds

17.8 EPA Safer Choice

17.9 ChemIDplus

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 EPA CPDat Classification

17.13 NORMAN Suspect List Exchange Classification

17.14 CCSBase Classification

17.15 EPA DSSTox Classification

17.16 Consumer Product Information Database Classification

17.17 EPA TSCA and CDR Classification

17.18 LOTUS Tree

17.19 EPA Substance Registry Services Tree

17.20 CCS Classification - Baker Lab

17.21 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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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. DTP/NCI
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  6. EPA Chemicals under the 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
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    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Human Metabolome Database (HMDB)
    LICENSE
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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. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    FA 20:0a
    CCS Classification - Baker Lab
    https://tarheels.live/bakerlab/
  13. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  14. 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/
    Eicosanoic Acid (20:0)
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  16. ChEBI
  17. 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/
  18. 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
  19. 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
  20. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. 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://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  21. Cosmetic Ingredient Review (CIR)
  22. EPA Chemical and Products Database (CPDat)
  23. 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
  24. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    arachidic acid
  25. KNApSAcK Species-Metabolite Database
  26. Natural Product Activity and Species Source (NPASS)
  27. West Coast Metabolomics Center-UC Davis
    FA 20:0; (arachidic acid)
  28. EPA Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  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 Europe
  31. 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
  32. 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
  33. SpectraBase
  34. Japan Chemical Substance Dictionary (Nikkaji)
  35. 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
  36. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    arachidic acid
  37. Metabolomics Workbench
  38. Nature Chemical Biology
  39. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  40. NMRShiftDB
  41. Protein Data Bank in Europe (PDBe)
  42. 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
  43. Springer Nature
  44. The Cambridge Structural Database
  45. Wikidata
  46. Wikipedia
  47. Wiley
  48. PubChem
  49. 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
  50. GHS Classification (UNECE)
  51. EPA Substance Registry Services
  52. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  53. PATENTSCOPE (WIPO)
  54. NCBI
CONTENTS