SODIUM LAUROYL SARCOSINATE
General Information
| Mainterm | SODIUM LAUROYL SARCOSINATE |
| CAS Reg.No.(or other ID) | 137-16-6 |
| Regnum |
175.105 177.1200 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 23668817 |
| IUPAC Name | sodium;2-[dodecanoyl(methyl)amino]acetate |
| InChI | InChI=1S/C15H29NO3.Na/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);/q;+1/p-1 |
| InChI Key | KSAVQLQVUXSOCR-UHFFFAOYSA-M |
| Canonical SMILES | CCCCCCCCCCCC(=O)N(C)CC(=O)[O-].[Na+] |
| Molecular Formula | C15H28NNaO3 |
| Wikipedia | sodium lauroyl sarcosinate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 293.383 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 12 |
| Complexity | 260.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B y M C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A A A A A A C A D B g A Q C C A M A A A A I A A G Q G A A A A A A A A A A A A A G I A A A C A B I A g C A E A A A A B g C Q A A E Y i I C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 60.4 |
| Monoisotopic Mass | 293.197 |
| Exact Mass | 293.197 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 2 |
From Pubchem
Toxicity Profile
| Route of Exposure | Oral ; inhalation ; dermal |
|---|---|
| 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. |
| 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. |
| Toxicity Values | LD50: 175 mg/kg (Intravenous, Rat) LD50: 2.1 g/kg (Oral, Mouse) |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). |
| Minimum Risk Level | |
| 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) |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - N-acyl-alpha amino acids and derivatives |
| Direct Parent | N-acyl-alpha amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | N-acyl-alpha-amino acid - N-acyl-amine - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid salt - Carboxylic acid - Monocarboxylic acid or derivatives - Organic alkali metal salt - Organic zwitterion - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic salt - Organic sodium salt - Organic nitrogen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
From ClassyFire
Targets
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
From T3DB