3- Hydroxypropionate

Potassium permanganate oxidizes succinic acid to a mixture of malic and tartaric acid [133-37-9]. 3-Hydroxypropionic acid [503-66-2] is obtained with sodium perchlorate. Cerium(IV) sulfate in sulfuric acid medium oxidizes succinic acid to oxaloacetic acid (71). 

The catalyst is a cobalt carbonyl that is prepared in situ from cobaltous hydroxide, and nonylpyridine is the promotor. Oxidation of the aldehyde produces 3-hydroxypropionic acid. 1,3-Propanediol and 3-hydroxypropi-onic acid could also be produced from acrolein (Chaper 8). ... 

CoSANSE = [bis(salicylidene-N-(methyl-3>hydroxypropionate))] Co Punniyamurthy, T. Iqbal. J. Tetrahedron Lett., 1994, 35, 4007... 

Ansede JH, PJ Pellechia, DC Yoch (1999) Metabolism of acrylate to 3-hydroxypropionate and its role in dimethylsulfoniopropionate lyase indnction by a salt march sediment bacterium, Alcaligenes faecalis M3 A. Appl Environ Microbiol 65 5075-5081. 

With 3-hydroxypropionic or 4-hydroxybutyric acid very little or no phosphor diester bond formation occurred. 1753... 

Besides 3HB, several other HASCL are incorporated into PHAs. This includes 3-hydroxypropionate (3HP),3-hydroxyvalerate (3HV), 4-hydroxybutyrate (4HB), 4-hydroxyvalerate (4HV), and 5-hydroxyvalerate (5HV). With only few exceptions these constituents are only incorporated into PHAs if precursor substrates are provided, and most of these polyesters cannot be synthesized from simple, structurally unrelated carbon sources. 

Ethyl a-bromoisobutyrate, 21, 53 Ethyl /3-bromopropionate, 20, 6S Ethyl caprylate, 20, 69 Ethyl carbonate, 23, 95, 97 Ethyl chlorocarbonate, 21, 81 2-Ethylchromone, 21, 42 Ethyl diacetylacetate, 21, 46 copper derivative, 21, 46 Ethyl a,a-DIMETHYL-/3-PHENYL-/3-hydroxypropionate, 21, S3 Ethylene chloride, 20, 28 22, 76 ETHYLENEDIAMINE, IV IV-DIBUTYL-, 23, 23... 

Microorganisms have also been developed to produce alternative products, such as lactic acid [65], propane-1,3-diol [67], 3-hydroxypropionic acid [68], butane-2,3-diol [69] and numerous other intermediates. For instance, bacteria such as the Clostridium acetobutylicum ferment free sugars to C4 oxygenates such as butyric acid or butanol. They form the C4 oxygenates by Aldol condensation of the acetaldehyde intermediates. The Weizmann process exploits this property to ferment starch feedstock anaerobically at 37 °C to produce a mixture of w-butanol, acetone and ethanol in a volume ratio of 70 25 5 [3],... 

Hydroxypropionic acid obtained by fermentation from glucose could also be a good candidate to produce various chemicals by catalytic routes [25]. 

In our first attempt to bind linker-modified bis(pyrazol-l-yl)acetic acids to a solid phase we used Merrifield resin, which is one of the most popular solid phase supports. Since Merrifield polymer was designed to bind carboxylic acids, we used the ester methyl 2,2-bis(3,5-dimethylpyrazol-l-yl)-3-hydroxypropionate (52) instead of the 2,2-bis(3,5-dimethylpyrazol-l-yl)-3-hydroxypropionic acid (49). 

Hydroxypropionic Acid (3-HPA). Like the structurally isomeric lactic acid, 3-HPA constitutes a three-carbon building block with the potential of becoming a key intermediate for a variety of high-volume chemicals malonic and acrylic acids, methacrylate, acrylonitrile, 1,3-propanediol, and so forth.Thus, Cargill is developing a low-cost fermentation route by metabolic engineering of the microbial... 

DOE, Energy, Efficiency and Renewable Energy, Top value added chemicals fi om biomass. Screening for potential candidates from sugars (a) Levulinic acid, pp. 45-48 (b) 3-Hydroxypropionic acid (3-HPA), pp. 29-31 (c) Four-carbon 1,4-diacids, pp. 22-25 (d) Itaconic acid, pp. 42-44 nrel.gov/docs/fy04osti/ 35523.pdf, 67 pp. 

Synonyms AI3-24257 AIDS-6024 Betaprone BPL BRN 0001360 Caswell No. 709 CCRIS 536 EINECS 200-340-1 EPA pesticide chemical code 010901 Hydracrylic acid p iactone 3-Hydroxypropionic acid lactone p Lactone NSC 21626 Oxetan-2-one 2-Oxetanone Propano-lide Propiolactone 1,3-Propiolactone 3-Propiolactone p Propionolactone 3-Propionolactone p Propro-lactone UN 2810. 

Hydroxyphenol, see Hydroquinone p-Hydroxyphenol, see Hydroquinone 4-Hydroxy-3-(l-phenyl-3-oxobutyl)coumarin, see Warfarin 1 -Hydroxypropane, see 1 -Propanol 3 Hydroxypropene, see Allyl alcohol 3 Hydroxypropionic acid lactone, see p-Propiolactone... 

Methanolysis of 0-propiolactone with a trace of hydroxide catalyst gives a good yield of methyl 3 -hydroxypropionic acid, but with an equimolecular quantity of sodium methoxide the product is sodium 3-methoxypropionate (equation 48) (64hc(19-2)729). 

Synonyms-. Hydracrylic acid, 3-lactone 3-hydroxypropionic acid, lactone 3-hydroxypropionic acid, P-lactone propanol ide 3-propanolide propiolactone 3-propiolactone P-propionolactone... 

As stated above, various authors have confirmed the extensive conversion of acrylic acid to carbon dioxide in rats and mice treated orally or topically. In addition, urinary metabolites include 3-hydroxypropionic acid and the mercapturic acid A-acet l-.S -(2-carboxyethyljcysteine and its. S -oxide (DeBethizy et al., 1987 Winter et al., 1993). 

The oxidation of aciy lic acid can be rationalized in terms of the endogenous catabolism of propionic acid, in which acrylyl coenzyme A is an intermediate. This pathway is analogous with fatty acid 3-oxidation, common to all species and, unlike the corresponding pathway in plants, does not involve vitamin 8,2. 3-Hydroxypropionic acid has been found as an intennediate in the metabolism of acrylic acid in vitro in rat liver and mitochondria (Finch Frederick, 1992). The CO2 excreted derives from the carboxyl carbon, while carbon atoms 2 and 3 are converted to acetyl coenzyme A, which participates in a variety of reactions. The oxidation of acrylic acid is catalysed by enzymes in a variety of tissues (Black Finch, 1995). In mice, the greatest activity was found in kidney, which was five times more active than liver and 50 times more active than skin (Black et al., 1993). 

Ethyl a,a-dimethyl-/3-phenyl- 3-hydroxypropionate may be prepared in a similar manner. For instance, from 100 g. of ethyl a-bromoisobutyrate and 65 g. of benzaldehyde, 82.5 g. (73 per cent of the theoretical amount) of ethyl a,a-dimethyl-/3-phenyl-/3-hydroxypropionate, boiling at i53-i58°/n mm., is obtained. It may be recrystallized by dissolving it at 30° in 100 cc. of ligroin (30-60°), chilling the solution for several days, and decanting the clear liquid from the precipitate m.p. 38.5-39°. 

Ethyl /3-phenyl-/3-hydroxypropionate has been prepared by esterification of /3-phenyl-/3-hydroxypropionic acid obtained by the addition of hydrogen bromide to cinnamic acid and subsequent hydrolysis.1,2 The procedure given is based on that of Andrijewski 3 and of Blaise and Herman.4... 

A cooled mixture of 200 g. (109 cc.) of concentrated sulfuric acid (2 moles) and 300 cc. of water is now added slowly with careful cooling (Note 2), the pasty mixture being stirred with a thermometer and the temperature not being allowed to rise above 35°- Sodium sulfate crystallizes during this addition. The mass is now shaken vigorously with 400 cc. of ether and allowed to stand for some minutes. The ether is then decanted as completely as possible and the residue filtered with suction. The sodium sulfate is now shaken with six successive 300-cc. portions of ether, the ether solutions being subsequently employed for extraction of the filtrate. This latter requires ro-r4 such extractions (each with 300-400 cc. of ether) for the satisfactory extraction of the /3-hydroxypropionic acid. The combined ethereal solution is dried over 50 g. of anhydrous sodium sulfate and the ether distilled from a water bath, the temperature of which is not allowed to rise above 50°. The product is then concentrated under reduced pressure from a water bath maintained at 55-60°. The residue should have attained constant weight after four to six hours of this treatment it consists of a sirupy liquid of pale straw color which contains 75-80 per cent of /3-hydroxypropionic acid (by titration) (Note 3). The yield is 120-225 g. (28-31 per cent of the theoretical amount). 

Hydroxypropionic acid is an uncrystallizable and hygroscopic sirup. The 20-25 Pcr cent °f impurity remaining in the final product is largely water. 

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