2-Hydroxypropanoic acid acids

Methanoic acid Ethanoic acid Octadecanoic acid 2 Hydroxypropanoic acid... 

Other Syntheses. Acryhc acid and other unsaturated compounds can also be made by a number of classical elimination reactions. Acrylates have been obtained from the thermal dehydration of hydracryhc acid (3-hydroxypropanoic acid [503-66-2]) (84), from the dehydrohalogenation of 3-halopropionic acid derivatives (85), and from the reduction of dihalopropionates (2). These studies, together with the related characterization and chemical investigations, contributed significantly to the development of commercial organic chemistry. 

Lactic acid [50-21-5] (2-hydroxypropanoic acid), CH CHOHCOOH, is the most widely occurring hydroxycarboxylic acid and thus is the principal topic of this article. It was first discovered ia 1780 by the Swedish chemist Scheele. Lactic acid is a naturally occurring organic acid that can be produced by fermentation or chemical synthesis. It is present ia many foods both naturally or as a product of in situ microbial fermentation, as ia sauerkraut, yogurt, buttermilk, sourdough breads, and many other fermented foods. Lactic acid is also a principal metaboHc iatermediate ia most living organisms, from anaerobic prokaryotes to humans. 

Oxidation. Monochloroacetic acid [79-11-8] may be synthesized by the reaction of ethylene chlorohydrin with nitric acid [7697-37-2]. Yields of greater than 90% are reported (41). >Beta-chlorolactic acid (3-chloro-2-hydroxypropanoic acid) [1713-85-5] is produced by the reaction of nitric acid with glycerol monochlorohydrin (42). Periodic acid [10450-60-9] and glycerol monochlorohydfin gives chloroacetaldehyde [107-20-0] ia 50% yield (43). 

For some years, this type of vehicle was used in anionic electro deposition primers. However for automobiles cationic electro deposition primers are now preferred. The vehicles for cationic primers are proprietary but probably consist of the reaction product of epoxy resins and polyfunctional amines solubilized by the conversion of amine groups into salts using an acid such as lactic acid (2-hydroxypropanoic acid) [50-21-5] Alcohol-blocked... 

Chemical Designations - Synonyms 2-Hydroxypropanoic acid alpha-Hydroxypropionic acid Milk acid Racemic acid Chemical Formula CHjCHOHCOOH-HjO. 

Molecules that are not identical to their mirror images are kinds of stereoisomers called enantiomers (Greek encmtio, meaning "opposite"). Enantiomers are related to each other as a right hand is related to a left hand and result whenever a tetrahedral carbon is bonded to four different substituents (one need not be H). For example, lactic acid (2-hydroxypropanoic acid) exists as a pair of enantiomers because there are four different groups (—H, -OH, - CH3, -C02H) bonded to the central carbon atom. The enantiomers are called (-i-)-lactic acid and (-)-lactic acid. Both are found in sour milk, but only the (+) enantiomer occurs in muscle tissue. 

Hydroxy-1-propanesulfonic acid y-sultone, pi97 2-Hydroxypropanoic acid, LI, L2... 

S)-(-)-2-Bromo-3-hydroxypropanoic acid Propanoic acid, 2-bromo-3-hydroxy-,... 

Serine (Ser or S) ((S)-2-amino-3-hydroxypropanoic acid) is a polar, neutral, uncharged amino acid with the formula H00CCH(NH2)CH20H. It has an aliphatic hydroxyl side chain and can be seen as a hydroxylated version of Ala. Ser participates in the biosynthesis of purines and pyrimidines and is also the precursor to several amino acids including Gly, Cys, and Trp (in bacteria). In addition, it is the precursor to numerous other metabolites, including sphingolipids and is present in enzymes such as a-chymotrypsin. Ser, Asn, and aspartate disrupt a helices. 

D-Erythrose has also been exposed to a boiling solution in pH 4.5 buffer. Low yields (<0.2%) of a number of products were obtained, as shown in Scheme 3. These included 5-(hydroxymethyl)-2-furaldehyde (11), 2-acetyl-5-(hydroxymethyl)furan (12), 3,4-dihydroxyacetophenone (13), 3,4-dihydroxy be nzaldehyde (14), 3,4-dihydroxybenzoic acid (15), 2,3-dihydroxytoluene (16), and 1,2-benzenediol (pyrocatechol) (17). Also detected were formic, hydroxyacetic, and 3-hydroxypropanoic acids. Pyrocatechol seems to be a product formed from all carbohydrates boiled in aqueous solutions at pH 4-10 it may constitute a statistical product arising from retro-aldol and re-aldol reactions. It has been shown that the aldol reaction may operate at a pH as low as 4. An aldol reaction... 

To illustrate what is meant by optical isomerism, consider lactic acid (2-hydroxypropanoic acid). It contains a tetrahedral carbon atom (shown in black) with four different groups attached. As a result, lactic acid exists as two distinct isomeric forms. 

Hydroformylation of methyl acrylate provides racemic methyl 2-formylpropanoate (Scheme 4.17, a-aldehyde) which can be enzymatically reduced to yield important chiral 3-hydroxypropanoic acid derivatives [154]. This reaction was catalyzed by the Rh/PNS (27) and Rh/PC (25) catalysts in... 

The hydrazide of 2,2-diphenyl-3-hydroxypropanoic acid was reduced with lithium aluminum hydride in 7V-ethylmorpholine at 100° to 3-amino-2,2-di-phenylpropanol in 72.5% yield [1145], Much more useful is reduction of N-arenesulfonylhydrazides of acids to aldehydes McFadyen-Stevens reduction) [284, 285] based on an alkali-catalyzed thermal decomposition according to Scheme 174. 

The condensation of various heterocycles (pyrimidine or purine) with allyl bromide has been effected in the presence of KI. This selectively afforded N-1 isomers with pyrimidines, but N-9, N-3 or N-9, N-7 isomer mixtures with purines (88MIP1 89MI12 91 Mil). Alkyl esters of 3-adenin-9-yl-2-hydroxypropanoic acids were reported as broad-spectrum antiviral agents (85JMC282). 

The names propanoic acid (systematic) and propionic acid (retained) are both approved for the unsubstituted acid. However, the acid CI-CH2-CH2-COOH must be named systematically as 3-chloropropanoic acid. The acid CH3-CH(OH)-COOH is known as lactic acid, if unsubstituted when it is substituted in position 3, for example with chlorine, the name becomes 3-chloro-2-hydroxypropanoic acid. Names such as 3-chloro-2-hydroxypropionic acid or 3-chlorolactic acid are not acceptable. 

Oxetan-2-one (j3-propanolactoiic) unci also oxetani-3-one are known, although most interest lies in the former compound. It is a carcinogen, possibly because it can alkylate guanidine, one of the constituent bases of nucleic acids. On standing, oxetan-2-one slowly polymerizes, and on pyrolysis it forms propenoic acid (Scheme 8.13). Alkaline hydrolysis gives a salt of 3-hydroxypropanoic acid. 

Ethyl Lactate Hydroxypropanoic Acid, Ethyl Ester Methyl Methacrylate... 

Ethylbenzene under Benzene and Monosubstituted Benzene Hydrocarbons Ethyl Chloride Chloroethane under Saturated Alkyl Halides Ethyl Lactate Hydroxypropanoic Acid, Ethyl Ester under Esters Ethylene under Alkenes, Cyclic Alkenes, and Dienes... 

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