65-82-7

Basic information

• Product Name: N-Acetyl-L-methionine
• Synonyms: ACETYL-L-METHIONINE;AC-MET-OH;AC-METHIONINE;N-ACETYL-L-MET;N-ACETYL-L-METHIONINE;N-AC-L-MET;N-AC-L-METHIONINE;N-ALPHA-ACETYL-L-METHIONINE
• CAS NO: 65-82-7
• Molecular Formula: C₇H₁₃NO₃S
• Molecular Weight: 191.25
• EINECS: 200-617-7
• Product Categories: Biochemistry;Pharmaceutical Intermediates;Amino Acid Derivatives;Methionine;Peptide Synthesis;99%min;amino;Amino Acid Derivatives;Amino Acids;Methionine [Met, M];Ac-Amino Acids;Amino Acids (N-Protected)
• Mol File: 65-82-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 103-106 °C(lit.)
• Boiling Point: 453.6 °C at 760 mmHg
• Flash Point: 228.1 °C
• Appearance: white crystals
• Density: 1.2684 (rough estimate)
• Vapor Pressure: 1.72E-09mmHg at 25°C
• Refractive Index: -21 ° (C=1, H2O)
• Storage Temp.: 0-6°C
• Solubility: methanol: soluble100mg/mL, clear, colorless
• PKA: 3.50±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,96
• BRN: 1725552
• CAS DataBase Reference: N-Acetyl-L-methionine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-methionine(65-82-7)
• EPA Substance Registry System: N-Acetyl-L-methionine(65-82-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• RTECS: PD0480000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 65-82-7(Hazardous Substances Data)

Usage

Identification Test

Take a sample of 250mg, get it dissolved it in 2.5ml isopropyl alcohol and get it diluted with water to 25ml. Take this liquid of 10ml and get it diluted with water to 100m1. Then take the liquid of 0.5,30 and 50μ1 after two dilutions. Drop it at the place with a distance of 2cm from the bottom edge of the thin-layer chromatographic plate. The plate is coated with silica gel (Namely, 20cm * 20cm Brinkman silica gel of 60.250nm, or the equivalent). In a sealed and balanced thin-layered chromatography expansion tank, The chromatography was splayed out by 10cm, and the developer was composed of n-butanol and the mixture of acetic acid and water in the proportion 75：20=20. Dry the plate overnight. Then spray the chromatography plate with a new iodoplatinate solution mixed with 10 percent chloroplatinic acid of 3ml, water of 97ml and 6 percent potassium iodide solution of 100ml. The sample shall be formed - a separate color spot with a Rf value of 0.67~0.1

Content Analysis

Weigh accurately about 250mg sample and put it in a flask with glass stopper. Add 100ml water, 5g dipotassium hydrogen phosphate, 2g potassium dihydrogen phosphate and 2g potassium iodide. Get it fully mixed and dissolved, plus 0. 1mol/L iodine solution of 50.0m1. Then stopper it and blend it. Leave it stand for 30 minutes and titrate excess iodine with 0.1mol / L sodium thiosulfate. Meanwhile conduct blank titration experiment. Iodine solution per Ml 0.1mol/L equals to this product (C7H13NO3S) 9.563mg.

Toxicity Grade

Safe for food(FDA，§172．372，2000).

Acute Toxicity

Vein - mouse LD50: 435 mg / kg

Use Quantity

Account for 3.1% of the total protein content in food (Calculated by free L- methionine). It shall not be used for infant food and food containing adding nitrite / nitrate (FDA, 172.3722000).

Chemical Properties

white crystals

Uses

N-Acetyl-L-methionine (CAS# 65-82-7) has been useful in the study of metabolic phenotypes of standard and cold-?stored platelets.

Definition

ChEBI: An L-methionine derivative that is L-methionine in which one of the amine hydrogens is substituted by an acetyl group.

Safety Profile

Poison by intravenous route. When heated to decomposition emits toxic fumes of NOX,.

Purification Methods

Crystallise N-acetyl-L-methionine from Me2CO, H2O or EtOAc. Dry it in a vacuum over P2O5. Its solubility at 25o in H2O is 30.7%, and in Me2CO it is 29.5%. [Mitzi & Schueter Biochim Biophys Acta 27 168 1958, Birnbaum et al. J Biol Chem 194 455 1952, Beilstein 4 IV 3206.]

InChI:InChI=1/C7H13NO3S/c1-5(9)8-6(7(10)11)3-4-12-2/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/p-1/t6-/m0/s1

Synthetic route

L-methionine (63-68-3) + acetic anhydride (108-24-7) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
In water for 0.0666667h; Irradiation;	98%
With sodium hydroxide at 0℃;
With acetic acid Heating;

acetamide (60-35-5) + 3-(methylsulfenyl)propanal (3268-49-3) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With dicobalt octacarbonyl; carbon monoxide; hydrogen In 1,4-dioxane at 68 - 72℃; under 97509.8 Torr; for 5.5h; Time; Concentration;	85.5%

acetamide (60-35-5) + 3-(methylsulfenyl)propanal (3268-49-3) + carbon monoxide (201230-82-2) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With lithium bromide; palladium(II) bromide In 1-methyl-pyrrolidin-2-one at 98 - 102℃; under 75007.5 Torr; for 6h; Product distribution / selectivity; Autoclave;	82.74%

L-methionine (63-68-3) + acetyl chloride (75-36-5) → N-acetyl-l-methionine (65-82-7)

L-methionine (63-68-3) + 4-nitrophenol acetate (830-03-5) → 4-nitro-phenol (100-02-7) + N-acetyl-l-methionine (65-82-7)

Conditions	Yield
β‐cyclodextrin In water; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; various conditions;

(Z)-2-Acetylamino-4-methylsulfanyl-but-2-enoic acid → N-acetyl-l-methionine (65-82-7) + N-acetyl-D-methionine (1509-92-8)

Conditions	Yield
With hydrogen; triethylamine; ClO4; (2S,4S)-MOD-BPPM In ethanol under 15200 Torr; for 24h; Ambient temperature; Title compound not separated from byproducts;

N-acetyl methionine amide (60325-30-6) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With potassium phosphate buffer at 30℃; for 1h; amidase from Erwina carotovora; determination of relative rate of deamination;

acetamide (60-35-5) + 3-(methylsulfenyl)propanal (3268-49-3) + carbon monoxide (201230-82-2) → N-acetyl-l-methionine (65-82-7) + N-acetyl-D-methionine (1509-92-8)

Conditions	Yield
With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide In various solvent(s) at 120℃; under 45003.6 Torr; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

4-carboxybenzophenone radical anion + C7H13NO3S*H(1+) → N-acetyl-l-methionine (65-82-7) + 4-carboxybenzophenone*

Conditions	Yield
In water Rate constant; pH = 5.5-6.0;

N-acetyl-L-methionine-L-alanine (17351-39-2) → L-alanin (56-41-7) + N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With silver nitrate; cisCl2 In water at 40 - 50℃; Kinetics; also with other dichloro palladium(II) dipeptide complex catalysts;
With perchloric acid; 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt; dinuclear palladium(II) hexaazacyclooctadecane In water-d2 at 50℃; pH=1.0; Kinetics; Further Variations:; molar ratios;

N-acetylated l-methionylglycine → N-acetyl-l-methionine (65-82-7) + glycine (56-40-6)

Conditions	Yield
With silver nitrate; cisCl2 In water at 40℃; Rate constant; also with other dichloro palladium(II) dipeptide complex catalysts;
With perchloric acid; 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt; dinuclear palladium(II) hexaazacyclooctadecane In water-d2 at 50℃; pH=0.98; Kinetics; Further Variations:; pH-values; Temperatures; molar ratios;

AcMet-ValH → L-valine (72-18-4) + N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With silver nitrate; cisCl2 In water at 40℃; Rate constant; also with other dichloro palladium(II) dipeptide complex catalysts;

L-methionine (63-68-3) + acetic anhydride (108-24-7) + aqueous alkali → N-acetyl-l-methionine (65-82-7)

N-acetylmethionine p-nitrophenyl ester (345909-82-2) → 4-nitro-phenol (100-02-7) + N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With water; bis[(benzyldimethylamino)chloropalladium(II)] In phosphate buffer at 25℃; pH=8.0; Kinetics;

N-acetyl-D-methionyl-L-proline → N-acetyl-l-methionine (65-82-7) + L-proline (147-85-3)

Conditions	Yield
With perchloric acid; 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt; dinuclear palladium(II) hexaazacyclooctadecane In water-d2 at 50℃; pH=1.0; Kinetics; Further Variations:; molar ratios;

AcMet-Ala-Ser → N-acetyl-l-methionine (65-82-7) + N-L-alanyl-L-serine (3303-41-1)

Conditions	Yield
With perchloric acid; 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt; dinuclear palladium(II) hexaazacyclooctadecane In water-d2 at 50℃; pH=1.0; Kinetics; Further Variations:; molar ratios;

N-benzoylmethionine (4703-38-2, 10290-61-6, 17966-61-9) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Hydrolysis.durch enzymatische Hydrolyse View Scheme
Multi-step reaction with 2 steps 1: soil bacteria View Scheme

acetic acid methyl ester (79-20-9) + DL-methionine (59-51-8) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With hydrogenchloride; sodium methylate In methanol; water

methylthiol (74-93-1) + 2,2-dichloro-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide (51524-71-1) → N-acetyl-l-methionine (65-82-7)

Conditions	Yield
With trimethylamine at 140℃; for 2.5h; Product distribution / selectivity;	24.5 %Chromat.
With triethylamine at 140℃; for 7h; Product distribution / selectivity;	19 %Chromat.
With N,N,N',N'-tetramethylguanidine at 70℃; for 2.5h; Product distribution / selectivity;	30.8 - 57.8 %Chromat.
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 70℃; for 2.5h; Product distribution / selectivity;	88 %Chromat.

methyl 2-acetamido-4-methylthiobutanoate (35671-83-1, 114285-15-3, 7451-74-3) → N-acetyl-l-methionine (65-82-7) + methyl acetyl-D-methioninate

Conditions	Yield
With Lecitase Ultra; water; calcium chloride at 30℃; for 12h; pH=8.5; aq. buffer; Enzymatic reaction; enantioselective reaction;

Upstream product

• 60325-30-6 N-acetyl methionine amide 
• 79-20-9 acetic acid methyl ester 
• 59-51-8 DL-methionine 
• 35671-83-1 methyl N-acetylmethionine 
• 60-35-5 acetamide 
• 3268-49-3 3-(methylsulfenyl)propanal 
• 1115-47-5 N-acetyl-DL-methionine 
• 201230-82-2 carbon monoxide 
• 63-68-3 L-methionine 
• 71-50-1 acetate 
• 35671-83-1 methyl 2-acetamido-4-methylthiobutanoate 
• 74-93-1 methylthiol 
• 51524-71-1 2,2-dichloro-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide 
• 4703-38-2 N-benzoylmethionine 

Downstream Products

• 1115-47-5 N-acetyl-DL-methionine 
• 902468-14-8 N-acetyl-L-methionyl-L-serine benzyl ester 
• 712270-02-5 (S)-3 N₂-acetyl-N₁-(2'-anilino-4,4'-bipyridin-2-yl)methioninamide 
• 1527499-55-3 1-acetyl-3-(5-cyclohexyl-1-hydroxypentylidene)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione 
• 59587-10-9 N-acetyl-L-methionine ethyl ester 
• 1367454-06-5 C₁₆H₂₂N₂O₄S 
• 1258550-68-3 (S)-4-(2-acetamido-4-(methylthio)butanamido)-N-(3-nitro-4-(2-(phenylthio)ethylamino)phenylsulfonyl)benzamide 
• 1355150-29-6 (S)-4-(2-acetamido-4-(methylthio)butanamido)benzoic acid 
• 1334394-71-6 C₁₆H₁₈Cl₂N₆O₂S 
• 76718-75-7 2-[4-(N-acetyl-DL-methionylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid 

Relevant articles and documents

Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres

Hepsin is a type II transmembrane serine protease (TTSP) associated with cell proliferation and overexpressed in several types of cancer including prostate cancer (PCa). Because of its significant role in cancer progression and metastasis, hepsin is an attractive protein as a potential therapeutic and diagnostic biomarker for PCa. Based on the reported Leu-Arg dipeptide-based hepsin inhibitors, we performed structural modification and determined in vitro hepsin- and matriptase-inhibitory activities. Comprehensive structure-activity relationship studies identified that the p-guanidinophenylalanine-based dipeptide analog 22a exhibited a strong hepsin-inhibitory activity (Ki = 50.5 nM) and 22-fold hepsin selectivity over matriptase. Compound 22a could be a prototype molecule for structural optimization of dipeptide-based hepsin inhibitors.

Synthesis method of (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid

The invention relates to a synthesis method of (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid and mainly aims to solve the technical problems of high cost, high pollution, numerous by-products andharm to mass production of the existing synthesis method. The method comprises the following steps: (1) dissolving solid L-methionine in a sodium carbonate aqueous solution, dropwise adding liquid acetic anhydride, stirring for reacting, filtering and washing unreacted acetic anhydride in filtrate by using a mixed solution of ethyl acetate and petroleum ether, adding an extraction agent which is ethyl acetate into a water phase, acidizing by using solid citric acid, layering, washing, drying and carrying out reduced-pressure distillation to obtain an intermediate which is Nalpha-acetyl-L-methionine; and (2) dissolving the intermediate which is Nalpha-acetyl-L-methionine in acetic acid, dropwise adding hydrogen peroxide with mass percentage concentration of 30%, stirring for reacting, concentrating an obtained product till the product is dry, adding alcohol and crystallizing to obtain the product which is (2S)-2-(acetamino)-4-(methylsulfinyl)butyric acid. The (2S)-2-(acetamino)-4-(methylsulfinyl) butyric acid is used as a raw material for synthesizing a polypeptide drug.

Peptide Tyrosinase Activators

Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.