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N-Lauroylsarcosine

PubChem CID
7348
Structure
N-Lauroylsarcosine_small.png
N-Lauroylsarcosine_3D_Structure.png
Molecular Formula
Synonyms
  • N-LAUROYLSARCOSINE
  • 97-78-9
  • Lauroyl sarcosine
  • Glycine, N-methyl-N-(1-oxododecyl)-
  • Lauroylsarcosine
Molecular Weight
271.40 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
N-Lauroylsarcosine is a N-acyl-amino acid.
Lauroyl sarcosine is a condensation product of natural fatty acids with sarcosine, which is a natural amino acid found in muscles and other body tissues. Acyl sarcosines are considered modifiŽed fatty acids in which the hydrocarbon chains are interrupted by an amidomethyl group in the alpha position. They are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines and their sodium salts are also used in the metal finishing and processing industries for their crystal modifying, anti-rust, and anti-corrosion properties. (L1892, A2881)
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107
L1892: Wikipedia. Sarcosine. Last Updated 16 October 2009. http://en.wikipedia.org/wiki/Sarcosine
See also: Sodium Lauroyl Sarcosinate (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-Lauroylsarcosine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
lauroyl-Sar-OH
Sequence
G
HELM
PEPTIDE1{[CCCCCCCCCCCC(=O)N(C)CC(=O)O]}$$$$
IUPAC
N-lauroyl-sarcosine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

2-[dodecanoyl(methyl)amino]acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C15H29NO3/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19/h3-13H2,1-2H3,(H,18,19)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

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

3.1.4 SMILES

CCCCCCCCCCCC(=O)N(C)CC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C15H29NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

97-78-9

3.3.3 Deprecated CAS

15535-18-9, 58392-41-9
15535-18-9

3.3.4 European Community (EC) Number

3.3.5 UNII

3.3.6 ChEBI ID

3.3.7 ChEMBL ID

3.3.8 DSSTox Substance ID

3.3.9 HMDB ID

3.3.10 NCI Thesaurus Code

3.3.11 Nikkaji Number

3.3.12 NSC Number

3.3.13 RXCUI

3.3.14 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Gardol
  • lauroyl sarcosine
  • N-dodecanoyl-N-methylglycine
  • N-lauroyl sarcosinate
  • N-lauroyl sarcosine
  • N-lauroyl-N-methylaminoacetic acid
  • N-lauroylsarcosinate
  • N-lauroylsarcosine
  • N-lauroylsarcosine sodium salt
  • N-methyl-N-(1-oxododecyl)glycine sodium salt (1:1)
  • sarcosyl NL
  • sarkosyl
  • sarkosyl L
  • sarkosyl NL
  • sarkosyl NL 30
  • sarkosyl, ammonium salt
  • sarkosyl, potassium salt
  • sodium lauroyl sarcosinate
  • sodium N-lauroyl sarcosinate
  • sodium N-lauroylsarcosinate
  • sodium N-laurylsarcosinate

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
271.40 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.5
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
271.21474379 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
271.21474379 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
254
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)

4.2 Experimental Properties

4.2.1 Physical Description

White hygroscopic powder; [Sigma-Aldrich MSDS]

4.3 Chemical Classes

Biological Agents -> Amino Acids and Derivatives

4.3.1 Cosmetics

Cosmetic ingredients (Lauroyl Sarcosine) -> CIR (Cosmetic Ingredient Review)
Surfactant; Antistatic; Cleansing; Hair conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4.3.2 Surfactants

Surfactant
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

Instrument Name
Varian A-60
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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5.1.2 13C NMR Spectra

1 of 2
Instrument Name
Bruker AM-270
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker AM-270
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 3
View All
NIST Number
236042
Library
Main library
Total Peaks
158
m/z Top Peak
131
m/z 2nd Highest
44
m/z 3rd Highest
41
Thumbnail
Thumbnail
2 of 3
View All
Source of Spectrum
Chemical Concepts, A Wiley Division, Weinheim, Germany
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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5.2.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

90.055 100

57.0699 6.56

95.0855 5.08

71.0855 4.96

85.1012 3.97

Thumbnail
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2 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

90.0549 100

272.2219 11.31

183.1743 3.07

228.0993 1.48

95.0855 1.18

Thumbnail
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5.2.3 LC-MS

1 of 18
View All
Authors
Erik Emke, Andrea Brunner, KWR
Instrument
Orbitrap Classic, Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35 eV FT-MS
Fragmentation Mode
CID
Column Name
XBridge C18 3.5um, 2.1x150mm, Waters
Retention Time
26.193 min
Precursor m/z
272.222
Precursor Adduct
[M+H]+
Top 5 Peaks

90.0548 999

254.2107 84

189.2326 18

130.0252 9

108.017 8

Thumbnail
Thumbnail
License
CC BY
2 of 18
View All
Authors
Erik Emke, Andrea Brunner, KWR
Instrument
Orbitrap Classic, Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35 eV FT-MS II
Fragmentation Mode
CID
Column Name
XBridge C18 3.5um, 2.1x150mm, Waters
Retention Time
26.193 min
Precursor m/z
272.222
Precursor Adduct
[M+H]+
Top 5 Peaks

90.0547 999

254.2107 89

189.232 10

189.2199 7

108.0939 6

Thumbnail
Thumbnail
License
CC BY

5.3 IR Spectra

5.3.1 FTIR Spectra

1 of 2
Technique
BETWEEN SALTS
Source of Sample
Hampshire Chemical Corporation, Nashua, New Hampshire
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
MELT-BETWEEN SALTS
Source of Sample
Novartis
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Detergents
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties. (See all compounds classified as Detergents.)

8.2 Metabolism / Metabolites

Acyl sarcosines can be absorbed following oral or dermal contact, while nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase. (A2878, A2879, L1892)
A2878: Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. PMID:17485391
A2879: Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. PMID:18218609
L1892: Wikipedia. Sarcosine. Last Updated 16 October 2009. http://en.wikipedia.org/wiki/Sarcosine

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Lauroyl Sarcosine
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
Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Acyl sarcosines are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines and their sodium salts are also used in the metal finishing and processing industries for their crystal modifying, anti-rust, and anti-corrosion properties. (A2881)
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107

9.1.1 Use Classification

Cosmetics -> Surfactant; Antistatic; Cleansing; Hair conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

9.1.2 Household Products

Household & Commercial/Institutional Products

Information on 25 consumer products that contain Lauroyl sarcosine in the following categories is provided:

• Auto Products

• Commercial / Institutional

• Inside the Home

• Personal Care

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Glycine, N-methyl-N-(1-oxododecyl)-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Corrosive
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H315 (89%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (71.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (28.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H330 (60%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H335 (24.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, 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 155 reports by companies from 6 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 (89%)

Eye Dam. 1 (71.6%)

Eye Irrit. 2 (28.4%)

Acute Tox. 2 (60%)

STOT SE 3 (24.5%)

10.1.3 Hazards Summary

A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Sarcosine hydrochloride.

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Glycine, N-methyl-N-(1-oxododecyl)-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Glycine, N-methyl-N-(1-oxododecyl)-: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Toxicity Summary

While acyl sarcosines themselves are not toxic, they are nitrosating agents. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (L1889, L1890, A2878, A2879, A2880, A2881)
A2878: Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. PMID:17485391
A2879: Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. PMID:18218609
A2880: Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. PMID:15380096
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107
L1889: Wikipedia. Nitrosamine. Last Updated 16 November 2009. http://en.wikipedia.org/wiki/Nitrosamine
L1890: Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. http://www.health-report.co.uk/ingredients-directory.htm

11.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity (not listed by IARC). (L135)

11.1.3 Health Effects

Acyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (A2881)
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107

11.1.4 Exposure Routes

Oral (A2881) ; inhalation (A2881) ; dermal (A2881)
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107

11.1.5 Symptoms

Acyl sarcosines may cause irritation to the skin and eyes. (A2881)
A2881: Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. PMID:11358107

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 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

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

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 ChemIDplus

17.5 ChEMBL Target Tree

17.6 UN GHS Classification

17.7 EPA CPDat Classification

17.8 NORMAN Suspect List Exchange Classification

17.9 EPA DSSTox Classification

17.10 Consumer Product Information Database Classification

17.11 EPA TSCA and CDR Classification

17.12 EPA Substance Registry Services Tree

17.13 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
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    https://www.nist.gov/srd/public-law
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. MassBank Europe
  22. 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
  23. 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
  24. SpectraBase
    N-Methyl-N-(1-oxododecyl)glycine
    https://spectrabase.com/spectrum/5idvEJriS4Z
    [Dodecanoyl(methyl)amino]acetic acid
    https://spectrabase.com/spectrum/GEylEIdLwmP
    N-Methyl-N-(1-oxo-dodecyl)-glycine
    https://spectrabase.com/spectrum/Drob61aQ1uW
    N-Methyl-N-(1-oxo-dodecyl)-glycine
    https://spectrabase.com/spectrum/AomGl9h6FSQ
  25. 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
  26. Springer Nature
  27. West Coast Metabolomics Center-UC Davis
    N-Lauroylsarcosine
  28. Wikidata
  29. PubChem
  30. 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
  31. GHS Classification (UNECE)
  32. EPA Substance Registry Services
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  34. PATENTSCOPE (WIPO)
CONTENTS