| Record Information |
|---|
| Version | 2.0 |
|---|
| Creation Date | 2009-11-20 00:56:56 UTC |
|---|
| Update Date | 2014-12-24 20:26:14 UTC |
|---|
| Accession Number | T3D3622 |
|---|
| Identification |
|---|
| Common Name | Lauroyl sarcosine |
|---|
| Class | Small Molecule |
|---|
| Description | 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 modified 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. (8, 4) |
|---|
| Compound Type | - Amide
- Amine
- Cosmetic Toxin
- Household Toxin
- Lachrymator
- Natural Compound
- Organic Compound
|
|---|
| Chemical Structure | |
|---|
| Synonyms | | Synonym | | (Dodecanoyl(methyl)amino)acetic acid | | Hamposyl l | | Lauroylsarcosine | | Maprosyl l | | N-dodecanoyl-n-methylglycine | | N-lauroyl sarcosinate | | N-lauroyl-n-methylaminoacetic acid | | n-lauroyl-Sarcosine | | N-lauroyl-Sarcosine (8CI) | | N-lauroylsarcosine | | N-lauroylsarcosine sodium salt solution | | N-laurylsarcosine | | N-Methyl-N-(1-oxododecyl) glycine | | N-methyl-N-(1-oxododecyl)-Glycine | | Sarcosyl l | | Sarkosyl | | Sarkosyl l |
|
|---|
| Chemical Formula | C15H29NO3 |
|---|
| Average Molecular Mass | 271.396 g/mol |
|---|
| Monoisotopic Mass | 271.215 g/mol |
|---|
| CAS Registry Number | 97-78-9 |
|---|
| IUPAC Name | 2-(N-methyldodecanamido)acetic acid |
|---|
| Traditional Name | gardol |
|---|
| SMILES | CCCCCCCCCCCC(=O)N(C)CC(O)=O |
|---|
| InChI Identifier | 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) |
|---|
| InChI Key | InChIKey=BACYUWVYYTXETD-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | N-acyl-alpha amino acids |
|---|
| Alternative Parents | |
|---|
| Substituents | - N-acyl-alpha-amino acid
- N-acyl-amine
- Tertiary carboxylic acid amide
- Carboxamide group
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Biological Properties |
|---|
| Status | Detected and Not Quantified |
|---|
| Origin | Exogenous |
|---|
| Cellular Locations | |
|---|
| Biofluid Locations | Not Available |
|---|
| Tissue Locations | Not Available |
|---|
| Pathways | Not Available |
|---|
| Applications | Not Available |
|---|
| Biological Roles | Not Available |
|---|
| Chemical Roles | Not Available |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Appearance | White powder. |
|---|
| Experimental Properties | | Property | Value |
|---|
| Melting Point | 28-36°C | | Boiling Point | Not Available | | Solubility | 0.0156 mg/mL | | LogP | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
|---|
| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-8910000000-9c0aca02bf332b3c35d7 | 2021-09-24 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0006-9000000000-0c21cfcd51fc37fa1d86 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-0006-9010000000-9efd146a59fcec39bf9b | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-0006-9000000000-d6a868a0fb6fbb42ab99 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-052f-9000000000-fd56e9d07dfa3f3f9d4e | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-000i-9010000000-db44bd91cc691e9dc14a | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 15V, Negative | splash10-000i-9050000000-01589d9126eb4d22e3f8 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-0a4i-9000000000-5254fbd1915f04b8f4ee | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0a4i-9000000000-a1e8067c7e5a5cdd15d1 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0a4i-9000000000-4df8acd1fe6dff4dc3ee | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Negative | splash10-000i-9000000000-8f0c95e2acd64d84482a | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 60V, Negative | splash10-000i-9000000000-b64915fbcae172d66178 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 75V, Negative | splash10-000i-9000000000-83875d710aab43e3f3f3 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-0006-9000000000-999a782c9b43d5f67d29 | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-3190000000-f5691b835c5d230bfb41 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006x-9320000000-f31dcd8e7a50da48d279 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-9200000000-d478a6c9401aaf7f8942 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-83fae2d4e0ac59334f5d | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fr-3290000000-6eb8787123d5468c024c | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-022l-9310000000-908cffbe1ba38e6745a5 | 2016-08-03 | View Spectrum |
|
|---|
| Toxicity Profile |
|---|
| Route of Exposure | Oral (4) ; inhalation (4) ; dermal (4) |
|---|
| Mechanism of Toxicity | 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. (6, 7, 1, 2, 3, 4) |
|---|
| Metabolism | 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. (1, 2, 8) |
|---|
| Toxicity Values | Not Available |
|---|
| Lethal Dose | Not Available |
|---|
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). (5) |
|---|
| Uses/Sources | 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. (4) |
|---|
| Minimum Risk Level | Not Available |
|---|
| 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. (4) |
|---|
| Symptoms | Acyl sarcosines may cause irritation to the skin and eyes. (4) |
|---|
| Treatment | Not Available |
|---|
| Normal Concentrations |
|---|
| Not Available |
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | Not Available |
|---|
| PubChem Compound ID | 7348 |
|---|
| ChEMBL ID | CHEMBL1907464 |
|---|
| ChemSpider ID | 7071 |
|---|
| KEGG ID | Not Available |
|---|
| UniProt ID | Not Available |
|---|
| OMIM ID | |
|---|
| ChEBI ID | Not Available |
|---|
| BioCyc ID | Not Available |
|---|
| CTD ID | Not Available |
|---|
| Stitch ID | Not Available |
|---|
| PDB ID | Not Available |
|---|
| ACToR ID | Not Available |
|---|
| Wikipedia Link | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| MSDS | T3D3622.pdf |
|---|
| General References | - 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. [17485391 ]
- 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. [18218609 ]
- 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. [15380096 ]
- 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. [11358107 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
- Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
- Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
- Wikipedia. Sarcosine. Last Updated 16 October 2009. [Link]
|
|---|
| Gene Regulation |
|---|
| Up-Regulated Genes | Not Available |
|---|
| Down-Regulated Genes | Not Available |
|---|
