Lauroyl lysine

• CAT Number: I030553
• CAS Number: 52315-75-0
• Molecular Formula: C18H36N2O3
• Molecular Weight: 328.49
• Purity: 98%
• Synonyms: Lauroyl lysine; N6-Lauroyl-L-lysine
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
• IUPAC Name: N6-dodecanoyl-L-lysine
• InChI: InChI=1S/C18H36N2O3/c1-2-3-4-5-6-7-8-9-10-14-17(21)20-15-12-11-13-16(19)18(22)23/h16H,2-15,19H2,1H3,(H,20,21)(H,22,23)/t16-/m0/s1
• InChIKey: GYDYJUYZBRGMCC-INIZCTEOSA-N
• SMILES: N[C@@H](CCCCNC(CCCCCCCCCCC)=O)C(O)=O

Lauroyl lysine (Cat.No:I030553) is an Amino Acid derivative that is made from natural coconut fatty acid (coconut oil). It is most often used as a hair and skin conditioning agent.

Reference

1: Koreishi M, Kawasaki R, Imanaka H, Imamura K, Takakura Y, Nakanishi K. Efficient Nepsilon-lauroyl-L-lysine production by recombinant epsilon-lysine acylase from Streptomyces mobaraensis. J Biotechnol. 2009 May 20;141(3-4):160-5. doi: 10.1016/j.jbiotec.2009.03.008. Epub 2009 Mar 27. PubMed PMID: 19433221.
2: Suzuki M, Abe T, Hanabusa K. Low-molecular-weight gelators based on N(alpha)-acetyl-N(epsilon)-dodecyl-L-lysine and their amphiphilic gelation properties. J Colloid Interface Sci. 2010 Jan 1;341(1):69-74. doi: 10.1016/j.jcis.2009.09.010. Epub 2009 Sep 13. PubMed PMID: 19846106.
3: Pérez L, Pinazo A, Teresa García M, Lozano M, Manresa A, Angelet M, Pilar Vinardell M, Mitjans M, Pons R, Rosa Infante M. Cationic surfactants from lysine: synthesis, micellization and biological evaluation. Eur J Med Chem. 2009 May;44(5):1884-92. doi: 10.1016/j.ejmech.2008.11.003. Epub 2008 Nov 14. PubMed PMID: 19070403.
4: Suzuki M, Yumoto M, Shirai H, Hanabusa K. Supramolecular gels formed by amphiphilic low-molecular-weight gelators of N alpha,N epsilon-diacyl-L-lysine derivatives. Chemistry. 2008;14(7):2133-44. PubMed PMID: 18161708.
5: Paquet A, Sarwar G. Determination of bioavailability of some long-chain N-substituted derivatives of L-methionine and L-lysine. Can J Biochem. 1980 Jul;58(7):577-80. PubMed PMID: 6778594.
6: Yang Y, Xu L, Gao Y, Wang Q, Che X, Li S. Improved initial burst of estradiol organogel as long-term in situ drug delivery implant: formulation, in vitro and in vivo characterization. Drug Dev Ind Pharm. 2012 May;38(5):550-6. doi: 10.3109/03639045.2012.665928. Epub 2012 Mar 15. PubMed PMID: 22420863.
7: Suzuki M, Nigawara T, Yumoto M, Kimura M, Shirai H, Hanabusa K. L-lysine based gemini organogelators: their organogelation properties and thermally stable organogels. Org Biomol Chem. 2003 Nov 21;1(22):4124-31. PubMed PMID: 14664402.
8: Suzuki M, Yumoto M, Kimura M, Shirai H, Hanabusa K. A family of low-molecular-weight hydrogelators based on L-lysine derivatives with a positively charged terminal group. Chemistry. 2003 Jan 3;9(1):348-54. PubMed PMID: 12506392.
9: Koreishi M, Zhang D, Imanaka H, Imamura K, Adachi S, Matsuno R, Nakanishi K. A novel acylase from Streptomyces mobaraensis that efficiently catalyzes hydrolysis/synthesis of capsaicins as well as N-acyl-L-amino acids and N-acyl-peptides. J Agric Food Chem. 2006 Jan 11;54(1):72-8. PubMed PMID: 16390180.
10: Chua MM, Fan ST, Karush F. Attachment of immunoglobulin to liposomal membrane via protein carbohydrate. Biochim Biophys Acta. 1984 Aug 21;800(3):291-300. PubMed PMID: 6432057.
11: Malatesta F, Darley-Usmar V, de Jong C, Prochaska LJ, Bisson R, Capaldi RA, Steffens GC, Buse G. Arrangement of subunit IV in beef heart cytochrome c oxidase probed by chemical labeling and protease digestion experiments. Biochemistry. 1983 Sep 13;22(19):4405-11. PubMed PMID: 6313039.
12: Chicharro C, Granata C, Lozano R, Andreu D, Rivas L. N-terminal fatty acid substitution increases the leishmanicidal activity of CA(1-7)M(2-9), a cecropin-melittin hybrid peptide. Antimicrob Agents Chemother. 2001 Sep;45(9):2441-9. PubMed PMID: 11502512; PubMed Central PMCID: PMC90675.
13: Sugimoto Y, Toyoshima S. Influence of chemical modification of N alpha-cocoyl-L-arginine ethyl ester on its hepatitis B surface antigen-inactivating effect. Antimicrob Agents Chemother. 1980 Oct;18(4):525-8. PubMed PMID: 7447415; PubMed Central PMCID: PMC284042.
14: Burnett CL, Heldreth B, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler DC, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Andersen FA. Safety Assessment of Amino Acid Alkyl Amides as Used in Cosmetics. Int J Toxicol. 2017 May/Jun;36(1_suppl):17S-56S. doi: 10.1177/1091581816686048. PubMed PMID: 28553738.
15: Crofcheck C, Maiti I, Pattanaik S, Jay M. Effect of ion and surfactant choice on the recovery of a histidine-tagged protein from tobacco extract using foam fractionation. Appl Biochem Biotechnol. 2004 Oct;119(1):79-92. PubMed PMID: 15496730.