52315-75-0

Basic information

• Product Name: N'-Laruoyl-L-lysine
• Synonyms: N-LAUROYL-L-LYSINE;N-ALPHA-LAUROYL-L-LYSINE;lauroyllysine;n6-(1-oxododecyl)-l-lysin;N-6-(1-oxododecyl)-L-Lysine;N-6-Lauroyl-L-lysine;L-Lysine, N6-(1-oxododecyl)-;N''-LARUOYL-L-LYSINE
• CAS NO: 52315-75-0
• Molecular Formula: C₁₈H₃₆N₂O₃
• Molecular Weight: 328.49
• EINECS: 261-742-0
• Mol File: 52315-75-0.mol

Chemical Properties

• Melting Point: 229-231 °C
• Boiling Point: 528 °C at 760 mmHg
• Flash Point: 273.1 °C
• Appearance: /
• Density: 0.994 g/cm³
• Vapor Pressure: 1.48E-12mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: 2-8°C
• PKA: 2.53±0.24(Predicted)
• CAS DataBase Reference: N'-Laruoyl-L-lysine(CAS DataBase Reference)
• NIST Chemistry Reference: N'-Laruoyl-L-lysine(52315-75-0)
• EPA Substance Registry System: N'-Laruoyl-L-lysine(52315-75-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 52315-75-0(Hazardous Substances Data)

Usage

Application

N-Lauroyl-L-lysine is a useful research chemical.

InChI:InChI=1/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

Synthetic route

lauric acid (143-07-7) + L-lysine (56-87-1) → N-lauroyl-L-lysine (59409-41-5) + Nε-lauroyl-L-lysine (52315-75-0)

Conditions	Yield
With Streptomyces mobaraensis NBRC 13819 acylase In glycerol at 37℃; for 48h; pH=7.5;	A 5% B 44%

tetrabutylphosphonium lysinate + methyl n-dodecanoate (111-82-0) → N-lauroyl-L-lysine (59409-41-5) + Nε-lauroyl-L-lysine (52315-75-0)

Conditions	Yield
at 80℃; for 54h; Inert atmosphere;	A 32% B 23%

ethanol (64-17-5) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-L-lysine ethyl ester (292140-08-0)

Conditions	Yield
With hydrogenchloride at 20℃;	96%

n-dodecanoyl chloride (112-16-3) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nε-bis(1-oxododecyl)-L-lysine (14379-54-5)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	96%
With sodium hydroxide In diethyl ether at 0 - 20℃;

suberoyl chloride (10027-07-3) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-suberoyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	96%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	82%

isononanoyl chloride (36727-29-4) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-(1-oxododecyl)-Nα-(3,5,5-trimethyl-1-oxohexyl)-L-lysine (783304-20-1)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	94%
With sodium hydroxide In diethyl ether at 0 - 20℃;

Nε-lauroyl-L-lysine (52315-75-0) + 2-heptyl-1-undecanoyl chloride → Nα-(2-heptyl-1-oxoundecyl)-Nε-(1-oxododecyl)-L-lysine

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	94%
With sodium hydroxide In diethyl ether at 0 - 20℃;

1-Decanol (112-30-1) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-L-lysine decyl ester (521974-57-2)

Conditions	Yield
Stage #1: 1-Decanol; Nε-lauroyl-L-lysine With toluene-4-sulfonic acid In benzene at 130℃; for 48h; Stage #2: With morpholine In methanol Further stages.;	93%
With toluene-4-sulfonic acid for 48h; Heating;	91%

gloutaric dichloride (2873-74-7) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-glutaryl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	93%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	79%

sebacoyl chloride (111-19-3) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-sebacoyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	93%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	83%

Nε-lauroyl-L-lysine (52315-75-0) + hexan-1-ol (111-27-3) → Nε-lauroyl-L-lysine hexyl ester

Conditions	Yield
With hydrogenchloride at 20℃;	93%

Nε-lauroyl-L-lysine (52315-75-0) + cyclohexanylcarbonyl chloride (2719-27-9) → Nα-(cyclohexylcarbonyl)-Nε-(1-oxododecyl)-L-lysine (755752-92-2)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	92%
With sodium hydroxide In diethyl ether at 0 - 20℃;

pimeloyl chloride (142-79-0) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-pimeloyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	92%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	82%

azelaoyl chloride (123-98-8) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-azelaoyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	92%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	82%

isononanol (3452-97-9, 140237-84-9, 140237-85-0) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-L-lysine 3,5,5-trimethylhexyl ester

Conditions	Yield
	90%

Adipic acid dichloride (111-50-2) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-adipoyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	90%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	80%

1-dodecyl alcohol (112-53-8) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-L-lysine dodecyl ester (340811-55-4)

Conditions	Yield
With toluene-4-sulfonic acid for 48h; Heating;	89%

succinoyl dichloride (543-20-4) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-succinyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	88%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	68%

Hexanoyl chloride (142-61-0) + Nε-lauroyl-L-lysine (52315-75-0) → Nα-hexanoyl-Nε-lauroyl-L-lysine (817203-60-4)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	88%
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	85%

Nε-lauroyl-L-lysine (52315-75-0) + 2-ethylhexanoic acid chloride (760-67-8) → Nα-(2-ethyl-1-oxohexyl)-Nε-(1-oxododecyl)-L-lysine

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	86%
With sodium hydroxide In diethyl ether at 0 - 20℃;

11-bromoundecanoyl chloride (15949-84-5) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-Nα-(11-bromoundecanoyl)-L-lysine

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; under 24 Torr;	85%
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	85%

1-Bromo-11-hydroxyundecane (1611-56-9) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-L-lysine 11-bromoundecyl ester (611610-44-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 130℃; for 48h;	80%

1,12-dodecanedioyl dichloride (4834-98-4) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-dodecanedioyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	80%

oxalyl dichloride (79-37-8) + Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-oxalyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether at 20℃; for 23h;	79%
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	65%

Nε-lauroyl-L-lysine (52315-75-0) + malonoyl dichloride (1663-67-8) → Nα,Nα'-malonyl-bis(Nε-lauroyl-L-lysine)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0 - 20℃; for 24h;	70%

ethyl 6-chloro-6-oxohexanoate (1071-71-2) + Nε-lauroyl-L-lysine (52315-75-0) → Nepsilon-lauroyl-Nalpha-(5-carboxypentanoyl)-L-lysine

Conditions	Yield
With water; sodium hydroxide at 20℃; for 24h;	66%

methanol (67-56-1) + Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-Nα-Cbz-lysine methyl ester hydrochloride

Conditions	Yield
With hydrogenchloride at 0 - 20℃;

Nε-lauroyl-L-lysine (52315-75-0) → Nε-lauroyl-Nα-(11-pyridiniumdecanoyl)-L-lysine bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / aq. NaOH / diethyl ether / 0 - 20 °C / 24 Torr 2: 98 percent / 24 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 85 percent / NaOH / H2O; diethyl ether / 24 h / 0 - 20 °C 2: 98 percent / 24 h / 100 °C View Scheme

Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-oxalyl-bis(Nε-lauroyl-L-lysine hexyl ester)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / HCl / 20 °C 2: 91 percent / Et3N / tetrahydrofuran / 24 h / 20 °C View Scheme

Nε-lauroyl-L-lysine (52315-75-0) → Nα,Nα'-oxalyl-bis(Nε-lauroyl-L-lysine 3,5,5-trimethylhexyl ester)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / Et3N / tetrahydrofuran / 24 h / 20 °C View Scheme

Upstream product

• 143-07-7 lauric acid 
• 56-87-1 L-lysine 
• 111-82-0 methyl n-dodecanoate 

Downstream Products

• 14379-54-5 N^α,N^ε-bis(1-oxododecyl)-L-lysine 
• 755752-92-2 N^α-(cyclohexylcarbonyl)-N^ε-(1-oxododecyl)-L-lysine 

Relevant articles and documents

Using the ionic liquid amino or N-acylated peptide dialkylsulfosuccinic N of manufacturing method

PROBLEM TO BE SOLVED: To provide a method for synthesizing N-acylamino acid or N-acylpeptide without using fatty acid chloride.SOLUTION: The method for producing N-acylamino acid or N-acylpeptide comprises a step of reacting ionic liquefied amino acid or peptide (A) with a fatty acid or ester thereof (B) under such a condition that a molar ratio of (A):(B) is 1:10 to 10:1.

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

A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 KDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55°C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10 2-104 times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of Nα-lauroyl-L-lysine, Nε-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.

Acylation of amino acids

N-mono-substituted derivatives of diamino acids are prepared by the reaction of succinimidyl esters of carboxylic acids or substituted carbonic acids with the unprotected diamino acid. The acylation preferentially occurs at the side chain or terminal amino group of the diamino acid. For example, selective acylation of the terminal amino group of lysine occurs without first having protected the 2-amino group. Such acylation has application in the preparation of inter alia N6 -palmitoyl-lysine.