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2006-11-18 02:18:41 · 3 answers · asked by Anonymous in Science & Mathematics Chemistry

3 answers

Thalidomide, first synthesized in 1953, was widely prescribed for morning sickness from 1957 to 1962, but only outside of the U.S. In 1961 the U.S. Food & Drug Administration was glad it had not given approval, because thalidomide became anathema when it was found to be seriously teratogenic (creating malformation in embryos, from the Greek for "monster") having caused serious birth defects in more than 10,000 babies. Now, a quarter of a century later, it appears that it may be a miracle drug for such diseases as AIDS, leprosy, lupus, and tuberculosis. Within the last year, and over the objection of groups focussed on the risk and seriousness of birth defects, the F.D.A. has approved its use with strict safeguards to protect women who are, or could become pregnant.

Since thalidomide has a stereogenic carbon atom, it exists as two enantiomers. Tests with mice in 1961 suggested that only one enantiomer was teratogenic while the other possessed the therapeutic activity. Unfortunately, subsequent test with rabbits showed that both enantiomers had both activities.



Racemic Mixtures

A mixture that contains equal amounts of a pair or enantiomers is called a racemic mixture or a racemate, a (±) pair, or a (d,l) pair. A racemic mixture is symbolized by placing (±) or (d,l) in front of the name of the compound.
Racemic mixtures are optically inactive. Since the enantiomers rotate plane polarized light in equal but opposite directions, the net result is an optical rotation of zero.

This invention affords a solution to the technical problem of obtaining one or both enantiomers of 5-substituted 4-hydroxyfuran-2-ones in pure form by resolution with enantiomerically pure bases. Racemic mixtures of 5-substituted 4-hydroxy-2(5H)-furanones, including 5-substituted and 5,5-disubstituted, 4-hydroxy and 3,4-dihydroxy furanones are separated into pure enantiomers by crystallization with an enantiomerically pure base, such as cinchonidine. In specific solvent mixtures, for example, 95% ethanol, the diastereomerically pure salt of one enantiomer crystallizes. The enantiomerically pure furanone can then be obtained simply by filtration and treatment of the salt with an acid, for example, trifluoracetic acid, followed by precipitation with water, filtration and drying. Moreover, the other enantiomer may be equally obtained in pure form by evaporation of the mother liquor, followed by the same treatment of the salt as described before.

http://www.ualberta.ca/~csps/JPPS1(1)/A.Mitchell/racemicview.htm
http://www.mixtures.info/racemic-mixture.html
http://members.aol.com/logan20/racemate.html

2006-11-18 02:29:07 · answer #1 · answered by c0mplicated_s0ul 5 · 0 0

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RE:
I need named examples of racemic mixtures?

2015-08-13 13:53:05 · answer #2 · answered by Stefanie 1 · 0 0

classic example is thalidomide. it racemizes insitu. google thalidomide. not a very pretty tale but its the classic example.

2006-11-18 15:49:36 · answer #3 · answered by Chinwe A 2 · 0 0

here http://www.ualberta.ca/~csps/JPPS1(1)/A.Mitchell/racemicview.htm

2006-11-18 02:27:31 · answer #4 · answered by Barry G 4 · 0 0

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