Ethyl lauroyl arginate

Ethyl lauroyl arginate
Names
IUPAC name
Ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate
Other names
Ethyl Nα-lauroyl-L-arginate
Lauric arginate ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
E number E243 (preservatives)
UNII
  • InChI=1S/C20H40N4O3/c1-3-5-6-7-8-9-10-11-12-15-18(25)24-17(19(26)27-4-2)14-13-16-23-20(21)22/h17H,3-16H2,1-2H3,(H,24,25)(H4,21,22,23)/t17-/m0/s1
    Key: XJTMYVOVQZMMKX-KRWDZBQOSA-N
  • CCCCCCCCCCCC(=O)NC(CCCN=C(N)N)C(=O)OCC
Properties
C20H40N4O3
Molar mass 384.565 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Ethyl lauroyl arginate HCl
Names
IUPAC name
ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride
Identifiers
3D model (JSmol)
ChemSpider
E number E243 (preservatives)
UNII
  • InChI=1S/C20H40N4O3.ClH/c1-3-5-6-7-8-9-10-11-12-15-18(25)24-17(19(26)27-4-2)14-13-16-23-20(21)22;/h17H,3-16H2,1-2H3,(H,24,25)(H4,21,22,23);1H/t17-;/m0./s1
    Key: CUBZMGWLVMQKNE-LMOVPXPDSA-N
  • CCCCCCCCCCCC(=O)NC(CCCN=C(N)N)C(=O)OCC.Cl
Properties
C20H41ClN4O3
Molar mass 421.02 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethyl lauroyl arginate (LAE) is a food preservative, antimicrobial compound, and drug more commonly known as E243.[1][2][3][4] It is used to treat dermatological disorders[2] and is often provided in the form of its hydrochloride salt. LAE is an amino acid-based surfactant with broad-spectrum antimicrobial activity, high biodegradability and low toxicity. Due to these features, LAE is a preservative used in food and cosmetic formulations.

  1. ^ "EU Approved additives and E Numbers". Food Standards Agency. Retrieved 3 December 2018.
  2. ^ a b "Compound Summary for CID 188214 - Ethyl Lauroyl Arginate". PubChem. NIH.
  3. ^ Yoshida R, Baba K, Santo T, Yoshimura I (1976). "Surfactants Derived from Amino Acids. III., Some surface-active properties and antimicrobial activities of the salts of long-chain Nα-acyl-L-arginine esters". Yukagaku = Journal of Japan Oil Chemists' Society. 25 (7): 404–408. doi:10.5650/jos1956.25.404.
  4. ^ WO 1996021642, Martinez-Pardo MR, Maestros AC, Serrabasa PE, "Use of cationic surfactants as sporicidal agents", issued 30 June 2009