132685-02-0

Basic information

• Product Name: PEAK E
• Synonyms: EBT;CONTAMINANT 97;1,1'-ETHYLIDENE-BIS(L-TRYPTOPHAN);1,1'-ETHYLIDENE-BIS(L-TRYTOPHAN);PEAK E;Tryptophan Related Compound A (15 mg) (1,1'-ethylidene-bis-(L-tryptophan));Tryptophan Related CoMpound A
• CAS NO: 132685-02-0
• Molecular Formula: C₂₄H₂₆N₄O₄
• Molecular Weight: 406.43
• Product Categories: Amino Acids & Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 132685-02-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 718.5°Cat760mmHg
• Flash Point: 388.4°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.14E-21mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: 0-6°C
• Solubility: Aqueous Base (Slightly)
• PKA: 1.95±0.10(Predicted)
• Stability: Decomposes under acidic condition, Hygroscopic
• CAS DataBase Reference: PEAK E(CAS DataBase Reference)
• NIST Chemistry Reference: PEAK E(132685-02-0)
• EPA Substance Registry System: PEAK E(132685-02-0)

Safety Data

• Hazardous Substances Data: 132685-02-0(Hazardous Substances Data)

Usage

Uses

1,1’-Ethylidenebis[L-tryptophan] is a L-tryptophan (T947210) contaminant found in the peripheral blood mononuclear cells from patients with functional somatic syndromes.

InChI:InChI=1/C24H26N4O4/c1-14(27-12-15(10-19(25)23(29)30)17-6-2-4-8-21(17)27)28-13-16(11-20(26)24(31)32)18-7-3-5-9-22(18)28/h2-9,12-14,19-20H,10-11,25-26H2,1H3,(H,29,30)(H,31,32)/t19-,20-/m0/s1

Synthetic route

acetaldehyde (75-07-0) + L-Tryptophan (73-22-3) → 1,1'-ethylidenebis (132685-02-0)

Conditions	Yield
With hydrogenchloride In water for 0.333333h;	30%

acetaldehyde (75-07-0) + L-Tryptophan (73-22-3) → 1,1'-ethylidenebis (132685-02-0) + (S)-2-Amino-3-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-propionic acid + (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (40678-46-4) + (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (42438-72-2)

Conditions	Yield
In water at 25℃; Product distribution; Kinetics; effect of pH, temperature and reactant concentration;

2,4-Dinitrofluorobenzene (70-34-8) + 1,1'-ethylidenebis (132685-02-0) → 1,1'-Ethylidenebis(N-2,4-dinitrophenyl-L-tryptophan)

Conditions	Yield
With sodium hydrogencarbonate In water; acetonitrile for 3h;	50%

1,1'-ethylidenebis (132685-02-0) + acetaldehyde (75-07-0) → (S)-2-Amino-3-[1-(1-hydroxy-ethyl)-1H-indol-3-yl]-propionic acid + L-Tryptophan (73-22-3) + (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (40678-46-4) + (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (42438-72-2)

Conditions	Yield
In water at 25℃; Rate constant; Product distribution; Thermodynamic data; kinetics; activation energy; effect of pH and temperature;

Upstream product

• 75-07-0 acetaldehyde 
• 73-22-3 L-Tryptophan 

Downstream Products

• 73-22-3 L-Tryptophan 
• 40678-46-4 (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 42438-72-2 (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 

Relevant articles and documents

1,1'-ETHYLIDENEBIS(L-TRYPTOPHAN), STRUCTURE DETERMINATION OF CONTAMINANT "97" - IMPLICATED IN THE EOSINOPHILIA-MYALGIA SYNDROME (EMS)

The condensation of tryptophan affords a bisindolylaminal of tryptophan which is indistinguishable from contaminant "97".The formation and decomposition of aminals is adressed in light of epidemiological evidence linking them to a recent outbreak of EMS.