Lauroyl alanine | CAS#52558-74-4 | fatty acid

MedKoo Cat#: 596788 | Name: Lauroyl alanine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lauroyl alanine is a fatty acid amide that may be used to support the physical gelation of binary mixtures of aliphatic and aromatic hydrocarbon solvents with potential use in injectable biodegradable drug delivery systems.

Chemical Structure

Lauroyl alanine

CAS#52558-74-4

Theoretical Analysis

MedKoo Cat#: 596788

Name: Lauroyl alanine

CAS#: 52558-74-4

Chemical Formula: C15H29NO3

Exact Mass: 271.2147

Molecular Weight: 271.40

Elemental Analysis: C, 66.38; H, 10.77; N, 5.16; O, 17.68

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks

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Synonym

Lauroyl alanine; Lauroylalanine; Aminiosurfact LA; N-Lauroyl-L-alanine;

IUPAC/Chemical Name

dodecanoyl-L-alanine

InChi Key

UYTOHYBIBPDOKX-ZDUSSCGKSA-N

InChi Code

InChI=1S/C15H29NO3/c1-3-4-5-6-7-8-9-10-11-12-14(17)16-13(2)15(18)19/h13H,3-12H2,1-2H3,(H,16,17)(H,18,19)/t13-/m0/s1

SMILES Code

CCCCCCCCCCCC(N[C@H](C(O)=O)C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

N-Lauroyl-L-alanine is an alanine derivative.

In vitro activity:

The amide-functionalized analogue N-lauroyl-l-alanine-CONH2 was demonstrated to gel a broad range of solvents from diesel to THF at MGCs of 2.5% w/v or less, as well as to produce gels with a higher thermal stability (ca. 30 °C) and enhanced mechanical properties (5 times increase in complex modulus), compared to the carboxylic acid analogue, N-lauroyl-l-alanine-COOH. Reference: ACS Omega. 2020 Jul 23;5(30):18758-18765. https://pubmed.ncbi.nlm.nih.gov/32775877/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 271.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen J, Boott CE, Lewis L, Siu A, Al-Debasi R, Carta V, Fogh AA, Kurek DZ, Wang L, MacLachlan MJ, Hum G. Amino Acid-Containing Phase-Selective Organogelators: A Water-Based Delivery System for Oil Spill Treatment. ACS Omega. 2020 Jul 23;5(30):18758-18765. doi: 10.1021/acsomega.0c01821. PMID: 32775877; PMCID: PMC7408258. 2. Pal A, Srivastava A, Bhattacharya S. Role of capping ligands on the nanoparticles in the modulation of properties of a hybrid matrix of nanoparticles in a 2D film and in a supramolecular organogel. Chemistry. 2009 Sep 14;15(36):9169-82. doi: 10.1002/chem.200900304. PMID: 19650086.

In vitro protocol:

In vivo protocol:

TBD

1: Pei J, Yin H, Xu G, Yuan H, Liu X, Yang Y. Odd-Even Effect in Synthesis of Mesoporous Silica Using Long-Chain Acyl-L-Alanine Sodium Salt Templating. J Nanosci Nanotechnol. 2018 Aug 1;18(8):5842-5848. doi: 10.1166/jnn.2018.15394. PubMed PMID: 29458651. 2: Sivaramakrishna D, Swamy MJ. Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA. Chem Phys Lipids. 2016 Dec;201:1-10. doi: 10.1016/j.chemphyslip.2016.10.002. Epub 2016 Oct 19. PubMed PMID: 27771218. 3: Samanta SK, Subrahmanyam KS, Bhattacharya S, Rao CN. Composites of graphene and other nanocarbons with organogelators assembled through supramolecular interactions. Chemistry. 2012 Mar 5;18(10):2890-901. doi: 10.1002/chem.201102572. Epub 2012 Feb 1. PubMed PMID: 22298373. 4: Garcia-Bennett AE, Xiao C, Zhou C, Castle T, Miyasaka K, Terasaki O. Bicontinuous cubic mesoporous materials with biphasic structures. Chemistry. 2011 Nov 25;17(48):13510-6. doi: 10.1002/chem.201101831. Epub 2011 Oct 27. PubMed PMID: 22031461. 5: Pal A, Srivastava A, Bhattacharya S. Role of capping ligands on the nanoparticles in the modulation of properties of a hybrid matrix of nanoparticles in a 2D film and in a supramolecular organogel. Chemistry. 2009 Sep 14;15(36):9169-82. doi: 10.1002/chem.200900304. PubMed PMID: 19650086. 6: Six DA, Carty SM, Guan Z, Raetz CR. Purification and mutagenesis of LpxL, the lauroyltransferase of Escherichia coli lipid A biosynthesis. Biochemistry. 2008 Aug 19;47(33):8623-37. doi: 10.1021/bi800873n. Epub 2008 Jul 26. PubMed PMID: 18656959; PubMed Central PMCID: PMC2664092. 7: Bhattacharya S, Pal A. Physical gelation of binary mixtures of hydrocarbons mediated by n-lauroyl-L-alanine and characterization of their thermal and mechanical properties. J Phys Chem B. 2008 Apr 24;112(16):4918-27. doi: 10.1021/jp7104715. Epub 2008 Mar 29. PubMed PMID: 18373372. 8: Couffin-Hoarau AC, Motulsky A, Delmas P, Leroux JC. In situ-forming pharmaceutical organogels based on the self-assembly of L-alanine derivatives. Pharm Res. 2004 Mar;21(3):454-7. PubMed PMID: 15070096. 9: Koga K, Kawashima S, Murakami M. In vitro and in situ evidence for the contribution of Labrasol and Gelucire 44/14 on transport of cephalexin and cefoperazone by rat intestine. Eur J Pharm Biopharm. 2002 Nov;54(3):311-8. PubMed PMID: 12445561. 10: McEllistrem MC, Stout JE, Harrison LH. Simplified protocol for pulsed-field gel electrophoresis analysis of Streptococcus pneumoniae. J Clin Microbiol. 2000 Jan;38(1):351-3. PubMed PMID: 10618114; PubMed Central PMCID: PMC88722. 11: Murakami T, Kishimoto M, Kawakita H, Kisaki M, Kojima Y, Higashi Y, Amagase H, Fuwa T, Yata N. Enhanced rectal and nasal absorption of human epidermal growth factor by combined use of the absorption promoter and the synthetic polymer in rats. Eur J Drug Metab Pharmacokinet. 1991;Spec No 3:125-31. PubMed PMID: 1820866. 12: Fecycz IT, Campbell JN. Mechanisms of activation and secretion of a cell-associated precursor of an exocellular protease of Pseudomonas aeruginosa 34362A. Eur J Biochem. 1985 Jan 2;146(1):35-42. PubMed PMID: 3917921. 13: Zaĭtsev AN, Rogozhin SV, Shatrov GN, Davidovich IuA, Rakhmanina NL. [Toxicological characteristics of disodium salt of N-lauroyl-L-glutamic acid--a surface-active agent used in the food processing industry]. Vopr Pitan. 1984 Jul-Aug;(4):58-60. Russian. PubMed PMID: 6485298. 14: Delbarre A, Migliore-Samour D, Werner GH, Roques BP, Jollès P. 1H NMR studies of natural and synthetic immunostimulating peptides in aqueous solution. Eur J Biochem. 1981 Aug;118(2):355-61. PubMed PMID: 7285929.