Skip to main content
SpringerLink
Log in

On Schiff's bases and aldehyde-fuchsin: A review from H. Schiff to R.D. Lillie

  • Published:
Histochemistry Aims and scope Submit manuscript

Summary

In histochemistry aldehyde-fuchsin is widely regarded as an azomethine compound, though this hypothesis cannot explain the variety of reaction products. Infrared spectroscopy did not show a C=N bond. It was therefore deemed of interest to review chemical studies of aldehydefuchsin and other Schiff's bases by Schiff and his contemporaries. Schiff regarded reaction products of low molecular aliphatic aldehydes, e.g. acetaldehyde, and aromatic amines as diarylamines; aldehyde-fuchsin was assigned a 2∶3 (dye∶aldehyde) formula. These reactions were facilitated by alcohol and HCl. Others suggested condensation of two aldehyde molecules which carried a secondary and a tertiary amine respectively. Eibner proved that these compounds were ethylenes, not azomethines, and contained two secondary amines. Condensation of such bases produced ethylenic polymers, the Schultz's bases. Aromatic aldehydes readily yielded azomethines; aliphatic aldehydes formed −C=N− bonds only during prolonged heating. These findings are in agreement with recent chemical data. Clearly, the term Schiff's bases is not synonymous with azomethines, but denotes any reaction product of aldehydes and amines. In 1962, Lillie's histochemical studies confirmed “the secondary amine nature of aldehyde aryl amine condensation”. Thus, chemical and histochemical studies from Schiff in the 1860's to Lillie in the 1960's indicate that aldehyde-fuchsin is not an azomethine compound, but contains diarylamines and their derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Bangle R (1954) Gomori's paraldehyde-fuchsin stain. I. Physicochemical and staining properties of the dye. J Histochem Cytochem 2:291–299

    Google Scholar 

  • Buehner TS, Nettleton GS, Longley JB (1979) Staining properties of aldehyde fuchsin analogs. J Histochem Cytochem 27:782–787

    Google Scholar 

  • Calm A (1884) Ueber eine Reaktion der Aldehyde. Ber Dtsch Chem Ges 17:2938–2941

    Google Scholar 

  • Clapp LB (1957) Chemistry of the covalent Bond. Freeman, San Francisco

    Google Scholar 

  • Denffer Hv, Heidbrink V (1974) Dünnschichtchromatographische Untersuchung verschiedener Aldehydfuchsine. Acta Histochem 48:62–68

    Google Scholar 

  • Dewar MJS (1969) The molecular orbital theory of organic chemistry. McGraw-Hill, New York

    Google Scholar 

  • Eibner A (1897) Ueber Äthylidendiphenamin. Ber Dtsch Chem Ges 30:1444–1450

    Google Scholar 

  • Eibner A (1898) Zur Chemie der Schiffschen Basen. Ueber Diphenaminverbindungen aliphatischer Aldehyde. Justus Liebigs Ann Chem 302:335–370

    Google Scholar 

  • Eibner A (1903) Zur Kenntnis der Aldehyde. 2. Diphenaminverbindungen der Aldehyde. Justus Liebigs Ann Chem 328:121–131

    Google Scholar 

  • Eibner A, Koch E (1926) Zur Kenntnis der stickstoffhaltigen Kunstharze. Über die Schultzschen Basen. Z angew Chem 39:1514–1518

    Google Scholar 

  • Fischer E, Fischer O (1876) Zur Kenntnis des Rosanilins. Ber Dtsch Chem Ges 9:891–900

    Google Scholar 

  • Gomori G (1950) Aldehyde-fuchsin: a new stain for elastic tissue. Am J Clin Pathol 20:665–666

    Google Scholar 

  • Gustavson KH (1956) The chemistry of tanning processes. Academic Press, New York

    Google Scholar 

  • Hickinbottom WJ (1954) Aromatic amines derived from benzene and its homoloques. In: Rodd EH (ed) Chemistry of carbon compounds, vol III, part A.Elsevier, Amsterdam, pp 158–229

    Google Scholar 

  • Horobin RW, Kevill-Davies IM (1971) A mechanistic study of the histochemical reactions between aldehydes and basic fuchsin in acid alcohol used as a simplified substitute for Schiff's reagent. Histochem J 3:371–378

    Google Scholar 

  • Hückel W (1941) Organische Chemie. 2. Aufl. Akademische Verlagsgesellschaft, Leipzig

    Google Scholar 

  • Jaffe HH (1973) Resonance. In: Hampel CA, Hawley GG (eds) The enclyclopedia of chemistry, 3rd ed. Van Nostrand Reinhold, New York, pp 974–975

    Google Scholar 

  • Lillie RD (1954) Histopathologic technic and practical histochemistry, 2nd ed. Blakiston, New York

    Google Scholar 

  • Lillie RD (1962) The histochemical reaction of aryl amines with tissue aldehydes produced by periodic and chromic acids. J Histochem Cytochem 10:303–314

    Google Scholar 

  • Lillie RD (1965) Histopathologic technic and practical histochemistry, 3rd ed. Blakiston-McGraw-Hill, New York

    Google Scholar 

  • Meyer R (1897) Die Theerfarbstoffe. Zweiter Theil (1880–1883). Friedrich Vieweg und Sohn, Braunschweig

    Google Scholar 

  • Miller Wv (1892) Zur Chinaldinsynthese. Ber Dtsch Chem Ges 25:2072–2074

    Google Scholar 

  • Miller Wv, Phöchl J (1894) Ueber stereoisomere Anilverbindungen. Ber Dtsch Chem Ges 27:1296–1304

    Google Scholar 

  • Pauling L (1960) The nature of the chemical bond, 3rd ed. Cornell University Press, Ithaca

    Google Scholar 

  • Pratesi L (1884) Sul modo di comportarsi dell'aldeide formica coll'anilina. Gazz Chim Ital 14:351–356

    Google Scholar 

  • Puchtler H, Meloan SN, Brewton BR (1975a) On the history of basic fuchsin and aldehyde-Schiff reactions from 1862–1935. Histochemistry 41:185–194

    Google Scholar 

  • Puchtler H, Meloan SN, Brewton BR (1975b) On structural formulas of basic fuchsin and aldehyde-Schiff reaction products. Histochemistry 45:255–265

    Google Scholar 

  • Puchtler H, Meloan SN, Waldrop FS (1979) Aldehyde-fuchsin: Historical and chemical considerations. Histochemistry 60:113–123

    Google Scholar 

  • Rath H (1972) Lehrbuch der Textilchemie. 3. Aufl. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Schiff H (1865a) Action des aldéhydes sur les amines. C R Acad Sci (Paris) 60:32–33

    Google Scholar 

  • Schiff H (1865b) Sur quelques amides de la série toluique. C R Acad Sci (Paris) 60:913–916

    Google Scholar 

  • Schiff H (1865c) Note sur l'action des aldéhydes sur la rosaniline. C R Acad Sci (Paris) 61:45–75

    Google Scholar 

  • Schiff H (1866a) Eine neue Reihe organischer Diamine. Justus Liebigs Ann Chem Suppl III:343–370

    Google Scholar 

  • Schiff H (1866b) Eine neue Reihe organischer Diamine. Zweite Abtheilung. Justus Liebigs Ann Chem 140:92–137

    Google Scholar 

  • Schiff H (1866c) Action des aldéhydes sur la rosaniline. Bull Soc Chim France 5:291–292

    Google Scholar 

  • Schiff H (1867a) Sur les monoamines dérivées des aldéhydes. C R Acad Sci (Paris) 65:320–322

    Google Scholar 

  • Schiff H (1867b) Action des aldéhydes sur les alcaloides et des sulfites d'aniline. Bull Soc Chim France 7:443–447

    Google Scholar 

  • Schiff H (1867c) Derives de la rosaniline. C R Acad Sci (Paris) 64:182–184

    Google Scholar 

  • Schiff H (1871) Zeitschrift für Chemie. Gazz Chim Ital 1:376–381

    Google Scholar 

  • Schiff H (1887) Über Farbstoffbasen aus Furfurol. Justus Liebigs Ann Chem 239:349–385

    Google Scholar 

  • Schiff H (1892) Polymethylenbasen aus Benzidin und Tolidin. Ber Dtsch Chem Ges 25:1936–1940

    Google Scholar 

  • Schiff H (1901) Trennung von Amin- und Säurefunction in Lösungen von Aminsäuren mittels Formaldehyd. Justus Liebigs Ann Chem 319:59–76

    Google Scholar 

  • Sidgwick NV (1937) The organic chemistry of nitrogen, 2nd ed (revised by Taylor TWJ, Baker W). Clarendon Press, Oxford

    Google Scholar 

  • Sprung MM (1940) A summary of the reactions of aldehydes with amines. Chem Rev 26:297–338

    Google Scholar 

  • Staab HA (1962) Einführung in die theoretische organische Chemie. 3. Aufl. Verlag Chemie, Weinheim

    Google Scholar 

  • Trotman ER (1970) Dyeing and chemical technology of textile fibers, 4th ed. Griffin, London

    Google Scholar 

  • Walker JF (1964) Formaldehyde, 3rd ed. Reinhold, New York

    Google Scholar 

  • Wall G (1972) Über die Anfärbung der Neurolipofuscine mit Aldehydfuchsinen. Histochemie 29:155–171

    Google Scholar 

  • Wellington C, Tollens B (1885) Ueber einige Derivate des Formaldehyds. Ber Dtsch Chem Ges 18:3298–3311

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pathology, Medical College of Georgia, 30912, Augusta, Georgia, USA

    H. Puchtler & S. N. Meloan

Authors
  1. H. Puchtler
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. N. Meloan
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Puchtler, H., Meloan, S.N. On Schiff's bases and aldehyde-fuchsin: A review from H. Schiff to R.D. Lillie. Histochemistry 72, 321–332 (1981). https://doi.org/10.1007/BF00501774

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00501774

Keywords

Search

Navigation