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

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

Used in Medical Research:
PEAK E is used as a biomarker for identifying patients with functional somatic syndromes. Its presence in peripheral blood mononuclear cells can help researchers understand the underlying mechanisms of these conditions and potentially develop targeted therapies.
Used in Pharmaceutical Development:
PEAK E may be used as a starting point for the development of new drugs or therapies targeting functional somatic syndromes. By studying the compound's properties and interactions with biological systems, researchers can gain insights into potential therapeutic approaches.
Used in Diagnostics:
PEAK E could be utilized as a diagnostic tool to detect and monitor the presence of functional somatic syndromes in patients. This could aid in early diagnosis and treatment, improving patient outcomes.
Used in Toxicology Studies:
As a contaminant found in patients with specific health conditions, PEAK E may be studied in toxicology research to understand its potential effects on human health and to develop strategies for mitigating any adverse effects.

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.

Kinetics of the formation and decomposition of 1,1′-ethylidenebis[L-tryptophan], an eosinophilia myalgia syndrome-associated compound

1,1′-Ethylidenebis[L-tryptophan] (EBT), an impurity found in L-tryptophan associated with eosinophilia myalgia syndrome (EMS), has been suggested as one of the causative agents for EMS. High-performance liquid chromatography was used to study the kinetics of EBT formation and decomposition in buffer systems. Initial EBT decomposition was first-order with respect to EBT and strongly pH-dependent. The pH profile suggested that decomposition involved the addition of one proton. The value of the critical pH, above which the rate of EBT decomposition remained constant, was determined to be 4.8. The rate of EBT decomposition increased with increasing temperature, and the activation energy was calculated to be 12.5 kcal/mol. The rate of EBT formation decreased with increasing pH and decreasing temperature. The presence of excess acetaldehyde increased EBT formation to a lesser extent than did the presence of excess L-tryptophan. The results of this study are consistent with the hypothesis that EBT was formed during the absorption stage of the cation exchange operation in the commercial process that resulted in the formation of EMS-associated L-tryptophan.