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[ CAS No. 60372-77-2 ] {[proInfo.proName]}

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Chemical Structure| 60372-77-2
Chemical Structure| 60372-77-2
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Product Citations

Product Citations      Expand+

Ryu, Victor ; Chuesiang, Piyanan ; Corradini, Maria G. , et al. DOI:

Abstract: This study evaluated the changes in dispersibility in the aqueous phase, chem. stability, and antimicrobial activity of curcumin after being encapsulated in a lauric arginate Et ester (LAE) micelle. Stock curcumin-LAE solutions were prepared by titrating curcumin dissolved in ethanol into LAE aqueous solutions (pH 3.5). The LAE in the stock solutions inhibited the crystallization and prevented the chem. degradation of curcumin during storage at 20°C. The antimicrobial activity of the curcumin-LAE solutions against Escherichia coli (E. coli) and Listeria innocua (L. innocua) cocktails was assessed by exposing the sample to UV-A light (λ = 365 nm) for 5 min. For samples with both LAE and curcumin at pH 3.5 during irradiation, synergistic antimicrobial activity was observed The release of protein or nucleic acid from the cells indicated an increase in its membrane permeability after treatments which was due to LAE-facilitated interaction between the photosensitizer and the membrane. LAE could inactivate both bacteria within 10 min without UV-A light irradiation, only at pH 7, which shows that LAE's antimicrobial efficacy depends on the pH. Therefore, microbial inactivation by two mechanisms, photosensitization and permeability operating simultaneously, produced a curcumin-LAE solution that could inactivate bacteria at a broad pH range.

Keywords: Microbial photoinactivation ; Curcumin ; Lauric arginate ethyl ester ; Micelles ; Photosensitizer

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Ryu, Victor ; Uknalis, Joseph ; Corradini, Maria G. , et al. DOI: PubMed ID:

Abstract: This study investigated the mechanism of how lauric arginate Et ester (LAE) improves the photoinactivation of bacteria by curcumin after diluting the 100 μmol/L stock curcumin-LAE micelle solution to the concentration used during the treatment based on the curcumin concentration The photoinactivation of bacteria was conducted by irradiating the 1 μmol/L curcumin-LAE solution containing cocktails of Escherichia coli and Listeria innocua strains (7 log CFU/mL) for 5 min with UV-A light (λ = 365 nm). The changes in solution turbidity, curcumin stability, and bacterial morphol., viability, and recovery were observed using SEM, TEM, and live/dead cell assays. The study found that LAE enhances the photoinactivation of bacteria by increasing the permeability of cell membranes which could promote the interaction of reactive oxygen species produced by photosensitized curcumin with the cell components. The combination of curcumin and LAE was demonstrated to be more effective in inhibiting bacterial recovery at pH 3.5 for E. coli, while LAE alone was more effective at pH 7.0 for L. innocua.

Keywords: microbial photoinactivation ; curcumin ; lauric arginate ethyl ester ; photosensitizer ; reactive oxygen species

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Jianwei Zhang ; Kun Huang ; Xuetong Fan , et al. DOI:

Abstract: Typically, short- and long-chain lipids from oils exhibit different antimicrobial activities and therefore have been used in agriculture and aquaculture, biomedical therapeutic and antibacterial fields. However, these fatty acids have limitations in terms of bioactive efficacy, thermostability and aqueous solubility. In this study, water-soluble iso-fatty acid arginate hydrochloride derivatives with antimicrobial properties were produced by introducing branched (iso-) chain and other linear- (n-) chain fatty acids to the "arginine" amino acid molecule. The two-step synthetic route was straightforward and provided an efficient 88% and 76% product yields for ethyl n-oleoyl arginate hydrochloride and ethyl iso-oleoyl arginate hydrochloride, respectively. ATR-FT-IR, NMR, and LC-MS-Q-TOF techniques were used to thoroughly characterize and confirm the products. These arginate products had strong antimicrobial activities against Listeria innucua, a Gram-positive bacterium with minimum inhibitory concentrations and minimum bactericidal concentrations ranging from 1.8 μg mL[?1] to 29.1 μg mL[?1]. Therefore, the study demonstrated the development of a novel class of antimicrobial compounds from iso-fatty acids and arginates.

Keywords: antimicrobial ; ethyl lauroyl arginate ; iso-fatty acid arginate ; iso-oleic acid ; isostearic acid

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Product Details of [ 60372-77-2 ]

CAS No. :60372-77-2 MDL No. :MFCD11983056
Formula : C20H41ClN4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CUBZMGWLVMQKNE-LMOVPXPDSA-N
M.W : 421.02 Pubchem ID :25229630
Synonyms :
Ethyl Lauroyl Arginate Hydrochloride
Chemical Name :(S)-Ethyl 2-dodecanamido-5-guanidinopentanoate hydrochloride

Calculated chemistry of [ 60372-77-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.85
Num. rotatable bonds : 20
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 118.61
TPSA : 117.3 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 5.37
Log Po/w (WLOGP) : 4.02
Log Po/w (MLOGP) : 2.6
Log Po/w (SILICOS-IT) : 4.02
Consensus Log Po/w : 3.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.51
Solubility : 0.0129 mg/ml ; 0.0000307 mol/l
Class : Moderately soluble
Log S (Ali) : -7.59
Solubility : 0.0000109 mg/ml ; 0.0000000259 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.78
Solubility : 0.000697 mg/ml ; 0.00000166 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.99

Safety of [ 60372-77-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P280-P305+P351+P338+P310 UN#:3077
Hazard Statements:H318-H400 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 60372-77-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 60372-77-2 ]

[ 60372-77-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 112-16-3 ]
  • L‐arginine ethyl ester hydrochloride [ No CAS ]
  • [ 60372-77-2 ]
YieldReaction ConditionsOperation in experiment
98.10% With sodium hydroxide; In water; ethyl acetate; at 8 - 30℃;pH 7.3 - 7.5;Product distribution / selectivity; Example 2; 47.1 gm of L-arginine ethyl ester dihydrochloride was transferred to a flask containing 300 gm of water and was stirred for 10 minutes to obtain a clear solution. This solution was cooled to 8 C. Further, 75 gm of 20% sodium hydroxide solution was taken in an addition funnel and 37.5 gm of lauroyl chloride was charged in another addition funnel. The pH meter electrode was dipped into the ethyl ester solution in the flask. The pH of the solution was 2.4. The pH of the solution was adjusted to 7.5 by adding 20% sodium hydroxide solution. To the solution, lauroyl chloride and 20% sodium hydroxide were added simultaneously at the temperature of about 8 C. to 10 C. and the pH of the solution was maintained to 7.5. The addition of lauroyl chloride and 20% sodium hydroxide solution was carried out for 3 hours to obtain the solution containing trace white precipitate of (LAS). The solution containing thick white precipitate was then slowly allowed to attain the temperature of about 18 C. to 20 C. The pH of the solution was 7.3. A 250 gm of ethyl acetate was added to the above solution containing thick white precipitate with stirring and heated to a temperature of about 30 C. to get a mixture containing an organic phase and an aqueous phase. The mixture was held at the temperature of about 30 C. for 15 minutes. The mixture was allowed to settle and then separated. The organic phase was separated and the organic phase thus obtained was filtered at 25 C. to remove trace of the white precipitate. The filtered organic phase was charged in a distillation flask and distilled under vacuum at a temperature of about 50 C. to obtain a white crystalline hydrochloride salt of ethyl lauroyl arginate. (% Yield-98.10, HPLC purity-98.3%)
94.06% L-Arginine ethyl ester dihydrochloride (27.5 grams, 0.1 mole) is slurried in 100 mL of Tetrahydrofuran while stirring, triethyl amine (20.2 grams equivalent to 0.2 mole) is added dropwise and stirred for 30 mins, followed by dropwise addition of lauroyl chloride (22 grams, 0.1 mole) at 15C, stirred at room temperature for 2 hours followed by addition of triethyl amine(10.1 grams, 0.1 mole). Reaction mixture is stirred at 40 C until completion of the reaction (monitored by HPLC/TLC). Insoluble salt of triethylamine hydrochloride (30 grams) is filtered off, and solvent is evaporated to furnish 65 grams of crude product. Isolation followed as explained in Example 1 furnishes 39.6 grams of Lauroyl ethyl arginate hydrochloride (94.06% yield) of purity >99%.
  • 2
  • [ 60372-77-2 ]
  • [ 127-09-3 ]
  • [ 92071-96-0 ]
YieldReaction ConditionsOperation in experiment
98.5% In water; at 75 - 80℃; for 6h;Product distribution / selectivity; Example 5; Example 4 was repeated except that the reaction time was six hours rather than four hours. The results were as follows: Product weight 44.1 g % LAE hydrochloride 0.32% % LAE acetate 99.2% % Yield 98.5% The product had a melting point of 81-83 C. The results of Example 5 demonstrate that the process of the invention using ethyl acetate as the diluent, a reaction temperature 75-80 C. and a reaction time of six hours can produce product with exceptional purity and exceptional yield.
  • 3
  • [ 60372-77-2 ]
  • [ 629-25-4 ]
  • [ 1193347-26-0 ]
YieldReaction ConditionsOperation in experiment
96.5% In water; at 80 - 85℃; for 0.5h; Example 6; This example was carried out using the same equipment set-up as is described in Example 1. 42 g (0.1 mole) of LAE hydrochloride were added to the flask and heated to 65-70 C. to melt it. Thereafter, 23.34 g (0.105 mole) of powdered sodium laurate were added to the flask with agitation (the reaction was exothermic-the temperature rose to 85 C.). The reaction mixture was maintained at 80-85 C. for 30 minutes to complete the reaction. Subsequently, 300 g of ethyl acetate were added to the flask at 80 C. and the contents of the flask were agitated and held at 75 C. for 30 minutes. The contents of the flask were then filtered hot to remove the by-product salt precipitate. The by-product precipitate was washed with additional ethyl acetate diluent to remove any entrained product. The ethyl acetate diluent fractions were then removed under vacuuo at 70-75 C. and 50-60 mm Hg. The yield of the product was 57.31 g (96.5% yield). The HPLC assay of the product was as follows:
  • 4
  • [ 60372-77-2 ]
  • [ 79-14-1 ]
  • lauroyl arginine ethyl ester glycolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.2% Weigh 42.1 grams of LAE hydrochloride,Add 80 g of butyl acetate,Heated to 60 dissolved,9.5 g of pyridine was added,The reaction was stirred for 1 hour,To the reaction solution was added 20 g of water,After standing stratified to remove the water layer,The resulting organic layer was added 9.1 g of glycolic acid,The reaction was continued at 60 C for 3 hours with stirring,Cold to -5 2 hours crystallization,The resulting powder was filtered,dry,43.9 grams of product was obtained,Yield 95.2%.
  • 5
  • [ 143-07-7 ]
  • L-arginine ethyl ester hydrochloride [ No CAS ]
  • [ 60372-77-2 ]
YieldReaction ConditionsOperation in experiment
8.76 g With benzotriazol-1-ol; diisopropyl-carbodiimide; In isopropyl alcohol; at 45℃; for 30h;Green chemistry; 1) Weigh 11.08 g L-arginine ethyl ester hydrochloride,13.63 g lauric acid,17.26 g DIC and 0.7253 g HOBt were dissolved in 247.42 g of isopropanol,The reaction was heated and stirred at 45 C for 30 h.(2) After the reaction is complete, the solvent is removed by rotary evaporation.After washing the by-products, the filtrate is filtered to 240 ml.86.33 g of sodium chloride was added and allowed to stand overnight. The white solid was washed three times with cold water and dried to give 8.76 g of lauryl arginine ethyl ester hydrochloride. The purity was 96.35%.
  • 6
  • [ 60372-77-2 ]
  • [ 144-62-7 ]
  • C20H40N4O3*C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5 g With sodium hydroxide; In methanol; water; at 90℃; for 2h; 1.0 g of oxalic acid (purchased from Discovery Co., Ltd.) was dissolved in 50 mL of methanol, and an equivalent amount of NaOH was added, and the mixture was stirred at room temperature until a white solid precipitated. The solution was filtered with suction and washed with 30 mL of methanol three times to obtain sodium oxalate. Sodium oxalate is dissolved in 50mL of water to prepare an aqueous solution of sodium oxalate (A); 4.7g of <strong>[60372-77-2]lauroylarginine ethyl ester hydrochloride</strong> is dissolved in 40mL of water and heated to 90 C until the lauroylarginine ethyl salt Dissolve all the acid salts to make an aqueous solution of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> (B); add the sodium oxalate solution (A) slowly to the aqueous solution of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> at 90 C ( In B), the mixture is continuously stirred and reacted for 2 hours, cooled to room temperature, filtered, and the precipitate is sufficiently washed with purified water. The precipitate is dried under vacuum at 60 C. to obtain 5.0 g of an oxalate ion-pair compound.
  • 7
  • [ 60372-77-2 ]
  • [ 497-19-8 ]
  • C20H40N4O3*CHO3(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
4 g With sodium hydroxide; In water; at 90℃; for 2h; 1.0 g of oxalic acid (purchased from Discovery Co., Ltd.) was dissolved in 50 mL of methanol, and an equivalent amount of NaOH was added, and the mixture was stirred at room temperature until a white solid precipitated. The solution was filtered with suction and washed with 30 mL of methanol three times to obtain sodium oxalate. Sodium oxalate is dissolved in 50mL of water to prepare an aqueous solution of sodium oxalate (A); 4.7g of <strong>[60372-77-2]lauroylarginine ethyl ester hydrochloride</strong> is dissolved in 40mL of water and heated to 90 C until the lauroylarginine ethyl salt Dissolve all the acid salts to make an aqueous solution of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> (B); add the sodium oxalate solution (A) slowly to the aqueous solution of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> at 90 C ( In B), the mixture is continuously stirred and reacted for 2 hours, cooled to room temperature, filtered, and the precipitate is sufficiently washed with purified water. The precipitate is dried under vacuum at 60 C. to obtain 5.0 g of an oxalate ion-pair compound.
  • 8
  • [ 60372-77-2 ]
  • [ 54-86-4 ]
  • C20H40N4O3*C6H5NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.6 g In water; at 90℃; for 2h; Sodium niacin (purchased from Tishike (Shanghai) Chemical Industry Development Co., Ltd.) 2.0 g was dissolved in 50 mL of water to prepare a sodium nicotinate aqueous solution (A); 6.8 g of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> Dissolve in 40mL of water and heat to 90 C until the <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> is completely dissolved to prepare an aqueous solution of <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> (B); The saline solution (A) was slowly added to the <strong>[60372-77-2]lauroyl arginine ethyl ester hydrochloride</strong> aqueous solution (B), continuously stirred, reacted for 2 hours, cooled to room temperature, filtered, the precipitate was fully washed with purified water, and the precipitate was dried under vacuum at 60 C. That is, 7.6 g of a niacin ion pair compound was obtained.
  • 9
  • [ 60372-77-2 ]
  • [ 87-69-4 ]
  • C20H40N4O3*C4H6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.3 g With sodium hydroxide; In methanol; water; at 90℃; for 2h; Dissolve 2.0 g of tartaric acid (purchased from Tishila (Shanghai) Chemical Industry Development Co., Ltd.) in 50 mL of methanol, add the equivalent of NaOH, stir at room temperature until a white solid precipitates, filter with suction and wash with 30 mL of methanol three times to obtain sodium tartrate . Sodium tartrate is dissolved in 50mL of water to prepare an aqueous solution of sodium tartrate (A); 5.6g of <strong>[60372-77-2]lauroylarginine ethyl ester hydrochloride</strong> is dissolved in 40mL of water and heated to 90 C until the lauroylarginine ethyl salt The acid salt was completely dissolved to prepare an aqueous solution of lauryl arginine ethyl ester hydrochloride (B); the sodium tartrate aqueous solution (A) was slowly added to the aqueous solution of lauryl arginine ethyl ester hydrochloride at 90 C ( In B), the mixture is continuously stirred and reacted for 2 hours, cooled to room temperature, filtered, and the precipitate is sufficiently washed with pure water, and the precipitate is dried under vacuum at 60 C. to obtain 6.3 g of a tartaric acid ion-pair compound.
  • 10
  • Nα-lauroyl-arginine ethyl ester [ No CAS ]
  • [ 60372-77-2 ]
YieldReaction ConditionsOperation in experiment
96.4% With hydrogenchloride; for 0.5h; 4) Disperse the lauroyl arginine ethyl ester fine product described in step (3) with 1000 kg of petroleum ether to obtain a white turbid liquid. Pass in dry HCl gas to react for 0.5 hours, aeration rate of 250 L / min, and keep stirring. After completion, suction filtration and air drying were performed to obtain 77 kg of lauroyl arginine ethyl ester hydrochloride with a yield of 96.4% and a purity of 99.4%.
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