526-31-8

Basic information

• Product Name: L-ABRINE
• Synonyms: H-METRP-OH;L-ABRINE;ABRINE;ABRINE, L-;1-METHYL-L-TRYPTOPHAN;N-METHYLTRYPTOPHAN;N-ME-TRP-OH;N-ME-TRP-OH HCL
• CAS NO: 526-31-8
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• EINECS: 208-388-5
• Product Categories: Indoles;Tryptophans;Amino Acid Derivatives;Peptide Synthesis;Tryptophan
• Mol File: 526-31-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300 °C (dec.)(lit.)
• Boiling Point: 358.94°C (rough estimate)
• Flash Point: 219.4 °C
• Appearance: White powder
• Density: 1.272±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.74E-08mmHg at 25°C
• Refractive Index: 65 ° (C=1, 0.5mol/L NaOH)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.32±0.10(Predicted)
• Merck: 14,10
• BRN: 86638
• CAS DataBase Reference: L-ABRINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-ABRINE(526-31-8)
• EPA Substance Registry System: L-ABRINE(526-31-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 526-31-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light grey crystalline powder or crystals

Definition

ChEBI: A N-methyl-L-alpha-amino acid that is the Nalpha-methyl derivative of L-tryptophan.

Biochem/physiol Actions

An indoleamino acid that shows radical scavenging and antioxidant properties in vitro.

Purification Methods

Crystallise L-abrine from H2O or EtOH/H2O mixture and dry it for 2days at 60o in high vacuum; it has m 275-290o(dec with browning at 230o) and [] D +47.2o (c 2, 0.5N HCl) [Peter et al. Helv Chim Acta 46 577 1963]. [Gregory & Morley J Chem Soc 913 1968, Beilstein 22/14 V 40.]

InChI:InChI=1/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1

Upstream product

• 485-80-3 S-adenosyl-L-methionine 
• 73-22-3 L-Tryptophan 

Downstream Products

• 102174-11-8 (1Ξ,3S)-2-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 35214-76-7 (+/-)-(2-indol-3-yl-1-methoxycarbonyl-ethyl)-trimethyl-ammonium; iodide 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 141408-33-5 N^α-(tert-butoxycarbonyl)-N^α-methyl-L-tryptophan 
• 141408-80-2 Boc-(N-Me)Trp-Lys(CBz)-Asp(OBn)-Phe-NH₂ 
• 153507-82-5 Boc-(N-Me)Trp-Lys(CONH-Ph-o-Me)-(N-Me)Asp-Phe-NH₂ 
• 141408-81-3 Boc-(N-Me)Trp-Lys(CONH-Ph-o-Me)-Asp-Phe-NH₂ 
• 153507-91-6 Boc-(N-Me)Trp-Lys-Asp-Phe-NH₂ 
• 171007-24-2 3-(3'-indolyl)-(2S)-(N-methyl-N-phenylacetamino)-1,1-di(4''-methylphenyl)-1-propanol 
• 171007-15-1 (2S)-(N-benzoyl-N-methylamino)-3-(3'-indolyl)-1,1-di(4''-methylphenyl)-1-propanol 
• 171007-26-4 3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutyrylamino)-1,1-di(4'''-methylphenyl)-1-propanol 
• 171007-25-3 3-(3'-indolyl)-(2S)-(N-isovaleryl-N-methylamino)-1,1-di(4''-methylphenyl)-1-propanol 
• 171007-19-5 3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(2''-methylphenyl)-1-propanol 
• 171007-18-4 3-(3'-indolyl)-(2S)-(N-methylamino)-1,1-di(4''-methylphenyl)-1-propanol 

Relevant articles and documents

Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 μM.

Compounds and compositions for treating infection

Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.