Heterocyclic Compounds from Milk

A simple experiment showing the relationship between the hexoses and five-membered heterocyclic compounds is
available using a natural material, milk. Lactose ("milk-sugar"), comprising some 4 4 % of cows milk, on treatment with
hot dilute nitric aeid, hydrolyses to equal amounts of galactose and glucose which in turn are oxidized t o mueie and saccharic acids, respectively. Mucic acid (C6H100s)precipitates in the presence of saccharic acid due to its much greater insolubility, being a source for the compounds furan, pyrrole, and thiophen which can be identified on a small scale by
characteristic qualitative tests.

Mucic Acid
Milk (100 ml) is diluted with water (50 ml) and 2-3 ml of dilute acetic acid added with stirring t o precipitate the
eaesin and fats. The latter are filtered off using a fluted paper and IO-12 ml of about 5 M nitric scid added to the filtrate
which is evaporated to low bulk an a water-bath. On ewling, the precipitated mueic scid is collected and washed using a
Buchner funnel. This can be used directly or purified by dissolution in a little dilute alkali and reprecipitated by addition of a little dilute mineral acid, yielding a white powder (m.p. 206-214 decamp.') or can be identified under the microscope by addition of a drop of 5%potassium hydroxide t o s trace of the acid on a glass slide whence characteristic prisms
of potassium mueate are observed.

-%

CsHl0O8 2Ca0
GH.0
2CaC03 + 3H20
Furan
A little mu& acid is mixed with some calcium oxide and heated in a small test tube or crucible. A pine-wood splint
moistened with eonc. HC1 turns green2 indicating the evolution of furan. (Furfural gives the same test, hut gives a characteristic red color with a mixture of aniline and hydrochloric acid,3 unlike furan

CsHs08(NH1)2
ClHsN + NH3 2C02 4Hz0
~yrrole
A little mucic acid in a test tube is treated with a few drops of cone. ammonia solution till reaction ceases giving ammonium mueate. On heating this salt, a pine-woad splint moistened with cone. HCI is turned a deep red color when
placed in the vapor indicating the evolution of pyrmle."

Thiophen
C6HloOs B a s d C 4 H & BaO 2CO2 3Hz0
A little mucic aeid is mixed with some barium sulfide in a small test tube and heated whence thiophen is evolved. A
drop of cone. H2SOa containing a crystal of isatin on a glass rod placed in the vapor turns blue (the "iudophenin reaction"): this being characteristic for thiophen.

' Dean, J. A., Editor, "Lange's Handbookof Chemistry",

11th Ed., McGraw-Hill, New York, 1973, p. 7-286.

Cheronis, N. B., Entrikin, J. B., "Identification of Organic Compounds," Wiley-Interscience, New York, 1963, p. 392.
Finar I. L., "Organic Chemistry (Vol. I),.' 3rd Ed., Longmans-Green, London, 1959, p. 714.
Reference (31, p. 717.
"Reference (31, p. 715.

S. A. Institute of Technology
P. 0. Box 1.
lngle Farm, Australia, 5098

256 / Journal of Chemical Education

M. Lampard