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N-LAUROYL-L-ALANINE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

52558-74-4

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52558-74-4 Usage

Uses

N-Lauroyl-L-alanine is a useful research chemical compound.

Check Digit Verification of cas no

The CAS Registry Mumber 52558-74-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,5,5 and 8 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 52558-74:
(7*5)+(6*2)+(5*5)+(4*5)+(3*8)+(2*7)+(1*4)=134
134 % 10 = 4
So 52558-74-4 is a valid CAS Registry Number.

52558-74-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Lauroyl-L-alanine

1.2 Other means of identification

Product number -
Other names N-n-dodecanoyl (L)-alanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52558-74-4 SDS

52558-74-4Synthetic route

L-alanine,N-(1-oxododecyl)-,sodium salt

L-alanine,N-(1-oxododecyl)-,sodium salt

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
With hydrogenchloride for 2h; pH=3 - 4; Cooling with ice; Large scale;99%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

L-alanin
56-41-7

L-alanin

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide for 0.5h; Ambient temperature;98%
With sodium hydroxide at 3℃;
With sodium hydroxide In water; tert-butyl alcohol
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

Wang resin-bound Fmoc-L-alanine

Wang resin-bound Fmoc-L-alanine

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
Stage #1: Wang resin-bound Fmoc-L-alanine With piperidine In N,N-dimethyl-formamide at 20℃;
Stage #2: n-dodecanoyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;
Stage #3: With trifluoroacetic acid In dichloromethane at 20℃; for 18h;
98%
methyl 2-(dodecanoylamino)propanoate

methyl 2-(dodecanoylamino)propanoate

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 5℃; for 2h;97%
With sodium hydroxide In tetrahydrofuran; methanol; water at 0℃; for 2h;97%
With potassium hydroxide In methanol at 20℃; for 10h;
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 5h;928.8 mg
L-alanin
56-41-7

L-alanin

methyl n-dodecanoate
111-82-0

methyl n-dodecanoate

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
With magnesium oxide; potassium oxide at 20 - 40℃; for 3h; pH=10;90.33%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

D-Alanine
338-69-2

D-Alanine

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

Conditions
ConditionsYield
With alkali
2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

L-alanine,N-(1-oxododecyl)-,sodium salt

L-alanine,N-(1-oxododecyl)-,sodium salt

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50 - 70℃;99%
2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C36H62N4O4
1057479-80-7

C36H62N4O4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;52%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

(S)-2-Dodecanoylamino-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-2-Dodecanoylamino-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 12h;
2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

6-<4-Deoxy-4-(dodecanoyl-L-alanyl)amino-L-glycero-β-L-manno-heptopyranosylamino>-9H-purine

6-<4-Deoxy-4-(dodecanoyl-L-alanyl)amino-L-glycero-β-L-manno-heptopyranosylamino>-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: DCC / dimethylformamide / 12 h
2: Et3N / dimethylformamide / 24 h
View Scheme
2-(dodecanoylamino)propanoic acid
52558-74-4

2-(dodecanoylamino)propanoic acid

L-alanin
56-41-7

L-alanin

Conditions
ConditionsYield
With recombinant Streptomyces mobaraensis aminoacylase; water at 37℃; pH=7.5; aq. buffer; Enzymatic reaction;

52558-74-4Relevant academic research and scientific papers

Potential grape-derived contributions to volatile ester concentrations in wine

Boss, Paul K.,Pearce, Anthony D.,Zhao, Yanjia,Nicholson, Emily L.,Dennis, Eric G.,Jeffery, David W.

, p. 7845 - 7873 (2015)

Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg·L-1 β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg·L-1 β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg·L-1 required for the stimulatory effect on ethyl and acetate ester production observed in this study.

First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills

Bhattacharya,Krishnan-Ghosh

, p. 185 - 186 (2001)

From a two-phase mixture of water and oil (either commercial fuel or pure organic solvent), a simple amino acid derivative, N-lauroyl-L-alanine has been shown to be able to gelate the oil phase selectively; SEM and FT-IR provided molecular level insights into the process of gelation.

Synthesis method of N-lauroyl amino acid salt

-

Paragraph 0029-0033; 0039-0044, (2021/07/14)

The invention provides a synthesis method of N-lauroyl amino acid salt, which comprises the following steps: mixing amino acid, alkali or alkali metal salt and lauramide into a reaction container according to a certain proportion, and arranging a tail gas receiving device on the reaction container; stirring and reacting for a certain time at a certain temperature; after the reaction is finished, acidifying the reaction mixture by using a hydrochloric acid solution to precipitate the product, filtering and collecting the precipitate to obtain a purified product; carrying out forced air drying on the purified product to remove moisture, so as to obtain a dried product; and dissolving the product with ethanol, adding an alkali solution at a certain temperature, stirring to react for a period of time, cooling to crystallize, and carrying out suction filtration to obtain the lauroyl amino acid salt. Other substances are not used as solvents, the problems of too high production and waste treatment cost and environmental pollution caused by the fact that a large amount of solvents (such as acetone and the like) are used at present are solved, and the method is a green and economical synthesis method and has wide market prospects and social benefits.

Preparation method and application of N-lauroyl-L-alanine

-

Paragraph 0166; 0120; 0121; 0122; 0126; 0127; 0128; 0132, (2018/11/22)

The invention discloses a preparation method of N-lauroyl-L-alanine. The preparation method comprises the following steps: preparing L-alanine salt, preparing pasty N-lauroyl-L-alanine salt, and preparing an N-lauroyl-L-alanine crude product and the like. The invention further provides application of amino acid in the daily chemical field and industries such as agriculture and medicines. The aminoacid provided by the invention has high performance, and has an obvious effect in the aspects of bacterium inhibition, pesticide removal, peculiar smell elimination and the like.

Manufacturing technology for fatty acyl amino acid

-

Paragraph 0025; 0026; 0027, (2017/12/04)

The invention discloses a manufacturing technology for fatty acyl group amino acid. The invention is characterized in that fatty acid methyl ester and amino sodium are taken as raw materials, a one-step synthesis method is adopted for synthesizing N-fatty acyl amino acid sodium surfactant under the effect of a metallic oxide catalyst and the mole ratio of the raw materials fatty acid methyl ester to sodium amino acid is (1.2-1.8):(0.7-1). The raw material proportion is proper, the by-product is almost not generated, the product synthetic ratio is as high as 87% or above, the purity is high, the problems of a large amount of to-be-treated waste acid, complex operation technology, high raw material PC13 irritation, and the like, of the traditional acyl chloride process are overcome and the technology accords with the green chemical principle. The dosage of the catalyst is reasonable; the catalyst is utilized, so that the production efficiency is greatly increased in the preparation process, the production flow is shortened and the product quality is increased; the excellent product even can be directly used as a raw material in pharmacy industry.

Control of macroscopic helicity by using the sergeants-and-soldiers principle in organogels

Nam, Seong Ryong,Lee, Ho Yong,Hong, Jong-In

supporting information; experimental part, p. 6040 - 6043 (2009/05/27)

The creation of well-defined homochiral helical ribbon structures in the gel phase was demonstrated. The achiral gelator 1 consists of a central aromatic group for aromatic stacking and alkylamide groups that can participate in inter-molecular hydrogen bonds and van der Waals interactions. The gelators were synthesized by simple amide coupling in moderate yields. NMR experiments were performed to obtain the evidence for π-π interaction and hydrogen-bonding interaction in organogelator 1. The solvent polarity was varied by changing the methanol and chloroform composition. The gelation behavior of the gelators was tested in various organic solvents. The SEM images of xerogels exhibited the macroscopic aggregation modes of the gelators. The CD experiments reveal that the chiral property of gelators can be reflected within the aggregates of achiral 1 without changing the helical structure derived from the aggregates of 1.

Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

Pal, Asish,Ghosh, Yamuna K.,Bhattacharya, Santanu

, p. 7334 - 7348 (2008/02/04)

A variety of fatty acid amides of different naturally occurring l-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them l-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed.

GEL-STATE COMPOSITION

-

, (2008/06/13)

A gel-state composition useful as, e.g., a composition for perfume cosmetics which is translucent to milk-white, is creamy to solid, has an excellent appearance, gives neither a tacky feeling nor a cooped-up feeling during use, and has excellent spreadability. The gel-state composition is characterized by containing at least one N-acylamino acid (A) represented by the general formula (1) and at least one oily base (B):R1-CO-X (In the formula, R1 represents a C1-25, linear or branched, saturated hydrocarbon group or an unsaturated hydrocarbon group optionally containing an aromatic ring; and X represents an aliphatic or aromatic α-, β-, or γ-amino acid.)

Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus

Phoon, Chee Wee,Somanadhan, Brinda,Heng, Sabrina Cher Hui,Ngo, Anna,Ng, Siew Bee,Butler, Mark S.,Buss, Antony D.,Sim, Mui Mui

, p. 11619 - 11628 (2007/10/03)

A high throughput screen against POLO-like kinase 1 (Plk1), an anti-cancer target, identified an active extract from the fungus Arachniotus punctatus. Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) with IC50 values of 13 and 118 μM, respectively. A 12′-hydroxy analog of gymnastatin N, 3, was also isolated as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic acid moieties might be responsible for its bioactivity. Graphical Abstract.

Self-assembled organogels formed by mono-chain L-alanine derivatives

Luo,Liu,Liang

, p. 1556 - 1557 (2007/10/03)

The mono-chain L-alanine derivatives self-assemble into bilayer aggregates in a number of organic liquids and gelatinize the liquids.

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