Hydroxy Hydroxybutyric Acid

Apart from lactic and hydroxyacetic acids, other a- and P-hydroxy acids have been small-volume specialty products produced in a variety of methods for specialized uses. y-Butyrolactone [96 8-0] which is the monomeric inner ester of y-hydroxybutyric acid [591-81-17, is a large-volume chemical derived from 1,4-butanediol (see Acetylene-derived chemicals). 

Preparation of N-Hydroxysuccinimide Ester of L-(-) y-Benzyloxycarbonylamino-a-Hydroxy-butyric Acid A solution of 10.6 grams (0,042 mol) of L-(-)-7-benzyloxycarbonylamino-o-hydroxybutyric acid and 4.8 grams (0.042 mol) of N-hydroxysuccinimide in 200 ml of... 

The following chemicals were obtained commercially (Sigma Chemical Co.) and bioassayed with C. album and Amaranthus retroflexus L. (seeds collected in North Carolina in 1980) following identification DL-3-hydroxybutyric acid (DL-3-hydroxy-butyric acid as a Na salt) and L-3-phenyllactic acid (L-2-hydroxy-3-phenyl-propanoic acid). 

E. coli C. Kluyveri 4-hydroxy-butyryl-CoA dehydrogenase and R. eutropha phaC P(4HB) 4-hydroxybutyric acid and glucose 68... 

Mehta, A. K., Muschaweck, N. M., Maeda, D. Y., Coop, A., and Ticku, M. K. (2001) Binding characteristics of the gamma-hydroxybutyric acid receptor antagonist [3H](2 )-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene) ethanoic acid in the rat brain. J. Pharmacol. Exp. Then 299,1148-1153. 

Vicibactin (18) (previously called hydroxamate K (61a)) from Rhizobium legu-minosarum is a macrocyclic trilactone consisting of A -acetyl-Ai -hydroxy-D-Om and (/ )-3-hydroxybutyric acid (91). 

It may be stated at this point that the presence of a /3-hydroxy-butyrate fat in certain organisms is a matter of general biochemical importance. Usually /3-hydroxybutyric acid and the acetone bodies are derived from n-butyric acid directly. The unambiguous formation of jS-hydroxybutyric acid anhydrides from carbohydrates opens up new vistas its formation from acetaldehyde, and from pyruvic acid, through aldol intermediates can be understood without difficulty. Kirrmann s reaction, to which little attention has been paid, is at the same time an example of an oxygen shift, leading from hydroxyaldehydes to fatty acids. 

When male F-344 rats were injected with NNN-2 -14c, 75-95% of the dose was excreted in the 48 hr urine. In one experiment, the urine was collected in vessels containing DNP reagent. However, the DNPs of 4-hydroxy-l-(3-pyridyl)-l-butanone and 4-hy-droxy-4-C3-pyridy1)butanal were not detected. Since this was likely due to further oxidation in vivo, methods were developed for isolation of their probable oxidation products. This resulted in identification of the lactone, 5- C3-pyridyl)—tetrahydrofuran-2-one (1-2%), the keto acid, 4-(3-pyridyl).-4-oxobutyric acid (1-2%) and the hydroxy acid, 4-(3-pyridyl)-4-hydroxybutyric acid (26-40%) as urinary metabolites. These metabolites resulted. 

Carnitine, L-3-hydroxy-4-(trimethylammonium)butyrate, is a water-soluble, tri-methylammonium derivative of y-amino-jS-hydroxybutyric acid, which is formed from trimethyllysine via y-butyrobetaine [40]. About 75% of carnitine is obtained from dietary intake of meat, fish, and dairy products containing proteins with trimethyllysine residues. Under normal conditions, endogenous synthesis from lysine and methionine plays a minor role, but can be stimulated by a diet low in carnitine. Carnitine is not further metabolized and is excreted in urine and bile as free carnitine or as conjugated carnitine esters [1, 41, 42]. Adequate intracellular levels of carnitine are therefore maintained by mechanisms that modulate dietary intake, endogenous synthesis, reabsorption, and cellular uptake. 

Poly-[(R)-3-hydroxybutyric acid], PHB Butyric acid, 3-hydroxy-, D-(-)-, polyesters (8) Butanoic acid, 3-hydroxy-, (R)-, homopolymer (9) (29435-48-1)... 

Arterenol d-Arterenol d-Epinephrine Amylamine Phenethylamine Methylamine Ethylamine Choline Ethanolamine 0-Hydroxy propylamine 0-Aminopropionic acid 7-Aminobutyric acid Y-Amino-0-hydroxybutyric acid 0-Methylbutylamine Taurine... 

OFFICIAL NAMES Gamma-hydroxybutyrate (GHB), 4-hydroxy butyrate, gamma hydrate, gamma-hydroxybutyrate sodium, gamma hydroxybutyric acid, gamma-OH, sodium oxy-bate, sodium oxybutyrate... 

The hydroxy acid 3-hydroxybutyric acid is available as the fCisomer from the biodegradable polymer, Biopol (Chapter 19).45 A number of derivatives are accessible from the polymer itself (Scheme 4.12).46-47... 

Hydroxy-propionic acid 1,3-Propanediol, acrylamide, acrylic acid, acrylonitrile, ethyl-3-hydroxypropionic acid, L-alanine, L-serine, malonic acid, propiolactone, poly(3-HP), poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid) Polymers, fine chemicals Cao et al., 1999 Werpy and Petersen, 2004 Zhang etal., 2004 Patel etal., 2006... 

Degradation procedures analogeus to those used for mycobactin P (see above) showed the aromatic residue to be salicylic acid (2-hydroxy-6-methylbenzoic acid in mycobactin P) and the hydroxy acid to be (+)-( -hydroxybutyric acid ((-)-3-hydroxy-2-methylpentanoic acid in mycobactin P). Fatty acid side chains substantially different from those in mycobactin P a minor component contains a s-octadec-2-enoic acid (identical to the principal product in mycobactin P). The major substituents in the fatty acid side chain are Cis to C21 fragments of unknown constitution. 

Amino-3-hydroxybutyric Acid Trimethylbetaine Levocarnitine 4-Trimethylamino-3-hydroxybutyrate (/ )-3-Carboxy-2-hydroxy-/V,/V,/V-trimethyl-1 -propanaminium Hydroxide, Inner Salt... 

Disposition in the Body. Readily absorbed after oral administration, and extensively metabolised to active metabolites. A number of metabolites have been identified including (i) 4-(biphenyl-4-yl)-4-hydroxybutyric acid, (ii) biphenyl-4-ylacetic acid, (iii) (4 -hydroxybiphenyl-4-yl)acetic acid, and (iv) 4-hydroxy-(4 -hydroxybiphenyl-4-yl)butyric acid. About 40% of a dose is excreted in the urine in 24 hours. The major urinary metabolites are metabolite (iii), about 11% of the dose, and metabolite (iv), about 17% of the dose metabolites (i) and (ii) are excreted in amounts less than about 3% of the dose. Very little unchanged drug is excreted in the urine. Less than 2% of the dose is eliminated in the faeces in 24 hours. 

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