A potential impurity found in commercial preparations of L-tryptophan
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1,1'-Ethylidene-bis-(L-tryptophan)

Item No. 35804

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1'-ethylenebis-L-tryptophan
CAS Number
132685-02-0
Synonyms
  • Peak 97 Contaminant
  • Peak E Contaminant
  • Peak E Substance
Molecular Formula
C24H26N4O4
Formula Weight
434.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
1 M NaOH: Soluble
SMILES
CC(N1C2=CC=CC=C2C(C[C@H](N)C(O)=O)=C1)N3C4=CC=CC=C4C(C[C@H](N)C(O)=O)=C3
InChi Code
InChI=1S/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
InChi Key
DETVQFQGSVEQBH-PMACEKPBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    1,1'-Ethylidene-bis-(L-tryptophan) is a potential impurity found in commercial preparations of L-tryptophan.1 It increases the proliferation of EoL-3 eosinophilic leukemia cells, release of eosinophil cationic protein from isolated human peripheral blood eosinophils, and IL-5 production in isolated human T cells.2 1,1'-Ethylidene-bis-(L-tryptophan) (40 µg/kg) induces fascia thickening and increases mast cell infiltration, inflammation, and fibrosis in superficial adipose and panniculus carnosus tissues in mice as a model system of eosinophilia-myalgia syndrome.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Trucksess, M.W. Separation and isolation of trace impurities in L-tryptophan by high-performance liquid chromatography. J. Chromatogr. 630(1-2), 147-150 (1993).

    2. Yamaoka, K.A., Miyasaka, N., Inuo, G., et al. 1,1'-Ethylidenebis(tryptophan) (Peak E) induces functional activation of human eosinophils and interleukin 5 production from T lymphocytes: Association of eosinophilia-myalgia syndrome with a L-tryptophan contaminant. J. Clin. Immunol. 14(1), 50-60 (1994).

    3. Love, L.A., Rader, J.I., Crofford, L.J., et al. Pathological and immunological effects of ingesting L-tryptophan and 1,1'-ethylidenebis (L-tryptophan) in Lewis rats. J. Clin. Invest. 91(3), 804-811 (1993).