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| CAS No.: | 65-82-7 |
|---|---|
| Name: | N-Acetyl-L-methionine |
| Article Data: | 34 |
| Molecular Structure: | |
|
|
|
| Formula: | C7H13NO3S |
| Molecular Weight: | 191.251 |
| Synonyms: | Methionine, N-acetyl-, L-;L-Methionine, N-acetyl-;Acetyl-L-methionine;Methionamine;Acetylmethionin;(2S)-2-acetamido-4-methylsulfanyl-butanoate;Thiomedon;L-(N-Acetyl)methionine;Ac-L-Met-OH; |
| EINECS: | 200-617-7 |
| Density: | 1.202 g/cm3 |
| Melting Point: | 104-107 °C |
| Boiling Point: | 453.6 °C at 760 mmHg |
| Flash Point: | 228.1 °C |
| Appearance: | white crystals |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 24/25-36-26 |
| PSA: | 91.70000 |
| LogP: | 0.71970 |
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| Conditions | Yield |
|---|---|
| In water for 0.0666667h; Irradiation; | 98% |
| With sodium hydroxide at 0℃; | |
| With acetic acid Heating; |
| 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% |
- 60-35-5
acetamide
- 3268-49-3
3-(methylsulfenyl)propanal
- 201230-82-2
carbon monoxide
- 65-82-7
N-acetyl-l-methionine
| 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% |
- 63-68-3
L-methionine
- 830-03-5
4-nitrophenol acetate
A
- 100-02-7
4-nitro-phenol
B
- 65-82-7
N-acetyl-l-methionine
| Conditions | Yield |
|---|---|
| β‐cyclodextrin In water; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; various conditions; |
| 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; |
- 60325-30-6
N-acetyl methionine amide
- 65-82-7
N-acetyl-l-methionine
| Conditions | Yield |
|---|---|
| With potassium phosphate buffer at 30℃; for 1h; amidase from Erwina carotovora; determination of relative rate of deamination; |
- 60-35-5
acetamide
- 3268-49-3
3-(methylsulfenyl)propanal
- 201230-82-2
carbon monoxide
A
- 65-82-7
N-acetyl-l-methionine
B
- 1509-92-8
N-acetyl-D-methionine
| 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; |
A
- 65-82-7
N-acetyl-l-methionine
| Conditions | Yield |
|---|---|
| In water Rate constant; pH = 5.5-6.0; |
| 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; |
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Consensus Reports
EPA TSCA Chemical Inventory, JUNE 1993
Specification
1. Introduction of N-Acetyl-L-methionine
The IUPAC name of N-Acetyl-L-methionine is 2-acetamido-4-methylsulfanylbutanoic acid. With the CAS registry number 65-82-7, it is also named as L-Methionine, N-acetyl-. The product's categories are Amino Acid Derivatives; Amino Acids; Methionine [Met, M]; Ac-Amino Acids; Amino Acids (N-Protected); Biochemistry; Pharmaceutical Intermediates; Peptide Synthesis. It is white crystals which is aoluble in water, alcohol, alkaline solution and dilute inorganic acid, almost insoluble in ether. Wha's more, it is stable and incompatible with strong oxidizing agents. When heated to decomposition emits toxic fumes of NOx. The storage environment should be well-ventilated, low-temperature and dry.
2. Properties of N-Acetyl-L-methionine
The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.19; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 71.91 Å2; (11)Index of Refraction: 1.51; (12)Molar Refractivity: 47.62 cm3; (13)Molar Volume: 158.9 cm3; (14)Polarizability: 18.87×10-24 cm3; (15)Surface Tension: 45.7 dyne/cm; (16)Enthalpy of Vaporization: 78.15 kJ/mol; (17)Vapour Pressure: 1.72E-09 mmHg at 25°C; (18)Rotatable Bond Count: 5; (19)Tautomer Count: 2; (20)Exact Mass: 191.061614; (21)MonoIsotopic Mass: 191.061614; (22)Topological Polar Surface Area: 91.7; (23)Heavy Atom Count: 12; (24)Complexity: 172.
3. Structure Descriptors of N-Acetyl-L-methionine
You could convert the following datas into the molecular structure:
1). SMILES:O=C(N[C@H](C(=O)O)CCSC)C
2). 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)/t6-/m0/s1
3). InChIKey:XUYPXLNMDZIRQH-LURJTMIEBN
4. Toxicity of N-Acetyl-L-methionine
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 435mg/kg (435mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 262, 1970. |
5. Safety Information of N-Acetyl-L-methionine
Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 24/25-36-26
WGK Germany: 3
RTECS: PD0480000
HazardClass: IRRITANT
HS Code: 29309070
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
6. Use and Preparation of N-Acetyl-L-methionine
Preparation of N-Acetyl-L-methionine: It can be obtained by acetylation of L-methionine with excess acetic acid or acetic anhydride.
Uses of N-Acetyl-L-methionine: It is used as accessorysubstance. It also can react with hydrazinecarboxylic acid tert-butyl ester to get Ac-Met-NHNHBoc. This reaction needs reagents 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide and solvent dimethylformamide at ambient temperature. The yield is 41.9%.
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