Organic acids 3-hydroxypropionic acid

P-Hydroxy acids lose water, especially in the presence of an acid catalyst, to give a,P-unsaturated acids, and frequendy P,y-unsaturated acids. P-Hydroxy acids do not form lactones readily because of the difficulty of four-membered ring formation. The simplest P-lactone, P-propiolactone, can be made from ketene and formaldehyde in the presence of methyl borate but not from P-hydroxypropionic acid. P-Propiolactone [57-57-8] is a usehil intermediate for organic synthesis but caution should be exercised when handling this lactone because it is a known carcinogen. 

Lactic acid (2-hydroxypropionic acid, CH3CH0HC02H, boiling point 122°C, melting point 18°C, density 1.2060) is one of the oldest known organic acids. It is the primary acid constituent of sour milk and is formed by the fermentation of milk sugar (lactose) by Streptococcus lactis. 

Suthers, P.F. and Cameron, D.C. 2005. Production of 3-Hydroxypropionic Acid in Recombinant Organisms. United States Patent number 6852517. 

Urinary organic acid analysis is useful for differentiating isolated carboxylase deficiencies from the biotin-responsive multiple carboxylase deficiencies. P-Hydroxyisovalerate is the most common urinary metabolite observed in isolated P-methylcrotonyl-CoA carboxylase deficiency, biotinidase deficiency, biotin holo-carboxylase synthetase deficiency, and acquired biotin deficiency. In addition to P-hydroxy-isovalerate, elevated concentrations of urinary lactate, methylcitrate, and P-hydroxypropionate are indicative of multiple carboxylase deficiency. 

Suthers PF, Cameron DC (2001) Production of 3-hydroxypropionic acid in recombinant organisms. PCT WO 01-16346... 

Lactic acid (2-hydroxypropionic acid) is a naturally occurring multifunctional organic acid that is found in many food products, particularly in those which involve natural or processed fermented food preparations. Currently, more than 70% of lactic acid is used as acidulents, food preservatives, and feedstock for the manufacture of calcium stearoyl-2-lactylates in the baking industry. The consumption of lactic acid is estimated to be around 30 million lb in the US with an estimated increase of 6% per year. Therefore, lactic acid is an intermediate-volume specialty chemical used chiefly for food processing. 

Figure 7. Effect of organic acids on dissolution rate in 0.1 M CaClt with Nt sparging at 25°C and pH 5. Key A, acrylic , sulfosuccinic , sulfopropionic A, hydroxypropionic and polyacrylic.

Organic acid oxidation in conjugation with oxidation of CaS03 slurry was studied for seven acids. Degradation of adipic acid and other aliphatic and sulfo carboxylic acids was least at pH 4.3 with 1.0 mM dissolved Mn and greatest at pH 5.5 without Mn. Hydroxypropionic and hydroxyacetic acids inhibited sulfite oxidation and were less subject to degradation. Fumaric acid degraded faster than the other alternatives. 

Organic acids are normally stable to oxidation, but laboratory and pilot plant results (18) have shown that adipic acid oxidizes in conjugation with sulfite oxidation in the scrubber. This paper reports oxidative degradation rate of adipic acid as a function of pH and Mn concentration (19). Results are also presented on sulfopropionic, sulfosuccinic, succinic, hydroxypropionic, and hydroxyacetic acids (20). 

Waste or byproduct organic acids could be cost-effective alternatives. Adipic acid production by nitric acid oxidation of cyclohexanol/cyclohexanone generates byproduct consisting of glutaric and succinic acids which should perform like adipic acid. Air oxidation of cyclohexane to produce cyclohexanone as an intermediate for caprolactam generates a waste solution of adipic, hydroxyvaleric, glutaric, and other acids. This product should be comparable to a mixture of adipic and hydroxypropionic acids. 

L-serine (S)-(-)-serine Ser S L-2-amino-3-hydroxypropionic acid L-(-)-serine 2-amino-3-hydroxypropionic acid 3-hydroxyalanine. Naturally xcurring enantiomer of serine. Used in bixhemical research, as a dietary supplement, in culture media, microbiological tests, feed additive, mp = 228 (dec) [a]8°= -7 (c = 10.41 H2O) soluble in H2O, insoluble in organic solvents. Degussa AG Janssen Chimica Mitsui Toatsu Nippon Rikagakuyakuhin U.S. BioChem. 

Synonyms Acetonic acid Ethylidenelactic acid 1-Hydroxyethanecar-boxylic acid 1 -Hydroxyethane 1 -carboxylic acid 2-Hydroxypropanoic acid 2-Hydroxypropionic acid a-Hydroxypropionic acid Milk acid Propanoic acid, 2-hydroxy- Propionic acid, 2-hydroxy-Classification Organic acid... 

Lactic acid (2-hydroxypropionic acid) is perhaps the most widely occurring carboxylic acid in nature. The Swedish chemist Scheele first discovered it in 1780. It exists in two different forms (Fig. 1) the dextrorotatory form, called L(-i-)-lactic acid or (5)-lactic acid, and the levorotatory form, called D(-)-lactic acid or R)-lactic acid. The plus and minus signs indicate the direction of the rotation of plane-polarized light produced by a chemical. These 2 stereoisomers (scientifically known as enantiomers ) are produced by different enzymes [lactate dehydrogenases (LDH)] present in living organisms. In this chapter, they will be referred to as D-lactic acid (d-LA) and L-lactic acid (l-LA). Naturally formed lactic acid is usually in the l form, but d-LA may coexist with l-LA in some cases, especially if it is secreted by nonspecific microbes. 

Gokarn RR, Selifonova OV, Jessen HJ, Steven JG, Selmer T, Buckel W. (2001). 3-hydroxypropionic acid and other organic componnds. Patent Application PCT/US2001/... 

Hydroxypropionic acid (3-HP), which is also called hydracrylic acid or ethylene lactic acid, is a three-carbon nonchiral organic acid. Two functional groups (carboxyl and P-hydroxyl) provide 3-HP with high reactivity, and as a result, 3-HP is a promising chemical precursor for polymer materials and other chemical feedstocks. 

Analysis of organic acids of the urine reveals the picture of multiple carboxylase deficiency characterized by pronounced excretion of lactate and 3-hydroxyisovalerate, 3-methylcrotonylglycine, 3-hydroxypropionate and methylcitrate. 

Acute episodes are characterized by massive ketonuria. Amino acid analysis reveals large amounts of glycine in plasma and urine. The diagnosis is best made by organic acid analysis of the urine. The key compounds are methylcitrate and 3-hydroxypropionate. GCMS analysis for methylcitrate provides for a rapid and specific approach to prenatal diagnosis. 

H.J., Gort, S.J., Selmer, T., and Buckel, W. (2014) 3-hydroxypropionic acid and other organic compounds. US Patent US7186541 B2, U.S. Patent and Trademark Office, Washington, DC. 

Burk, M.J. and Osterhout, R.E. (2009) Methods and organisms for production of 3-hydroxypropionic acid. US Patent US20100021978 Al. 

Figure 1 Urinary organic acid chromatogram of a patient with propionic acidemia. Peak A is 3-hydroxypropionic acid, B is 2-methyl-3-hydroxybutyric acid, C is 3-hydroxy-iso-valeric acid, D is 3-hydroxy-/7-vaieric acid, peaks E represent propionylglycine, peak F is tigiyigiycine, peaks G are methyicitric acid. IS = internal standard (tricarballylic acid).

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