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Since a meso isomer has a superposable mirror image, a compound with a total of n chiral centers cannot attain the theoretical maximum of 2 n stereoisomers if one of the stereoisomers is meso. [4] A meso isomer need not have a mirror plane. It may have an inversion or a rotoreflexion symmetry such as S 4. For example, there are two meso isomers ...
These include meso compounds, cis–trans isomers, E-Z isomers, and non-enantiomeric optical isomers. Diastereomers seldom have the same physical properties. In the example shown below, the meso form of tartaric acid forms a diastereomeric pair with both levo- and dextro-tartaric acids, which form an enantiomeric pair.
myo-Inositol is a meso compound, meaning it is optically inactive because it has a plane of symmetry. [10] It is a white crystalline powder, relatively stable in the air. It is highly soluble in water, slightly soluble in glacial acetic acid , ethanol , glycol , and glycerin , but insoluble in chloroform and ether .
An enantiomeric pair (S,S)- and (R,R)-ethambutol, along with the achiral stereoisomer called meso-form, it holds a diastereomeric relationship with the optically active stereoisomers. The activity of the drug resides in the (S,S)-enantiomer which is 500 and 12 fold more potent than the (R,R)-ethambutol and the meso-form. The drug had initially ...
The compound exists as three stereoisomers, a pair of enantiomers and the meso isomer. All are colorless liquids. All are colorless liquids. Preparation and reactions
The unforeseen teratogenicity of the (R)-(+)-isomer caused it to become an important case study of stereochemistry in medicine. Although it is possible to chemically isolate just the desired (S)-(−)-isomer from the racemic mixture, the two enantiomers rapidly interconvert in vivo ; thus rendering their separation to be of little use.
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The meso-form is the second most abundant in nature, after 3R,3′R-zeaxanthin, which is produced by plants and algae. [1] Meso-zeaxanthin has been identified in specific tissues of marine organisms [2] and in the macula lutea, also known as the "yellow spot" of the human retina. [3] [4]