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Chemical Compound Review

3-hydroxybutyrate     (3R)-3-hydroxybutanoic acid

Synonyms: BHIB, AG-H-30486, CHEMBL1162484, CHEBI:17066, HMDB00011, ...
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Disease relevance of (R)-beta-Hydroxybutanoic acid


High impact information on (R)-beta-Hydroxybutanoic acid


Chemical compound and disease context of (R)-beta-Hydroxybutanoic acid


Biological context of (R)-beta-Hydroxybutanoic acid


Anatomical context of (R)-beta-Hydroxybutanoic acid


Associations of (R)-beta-Hydroxybutanoic acid with other chemical compounds


Gene context of (R)-beta-Hydroxybutanoic acid

  • These tumors induced numerous lymphatics at the invasive front, and compressed or destroyed VEGF receptor (R)-3-positive lymphatics were observed within the solid tumors [20].
  • Preferred conformations of (R)-3 are similar in shape to those of the stereoselective 5-HT1A-receptor agonist (2R,3S)-8-hydroxy-3-methyl-2-(dipropylamino)tetralin [21].
  • Enantiomers of 3 are noncompetitive inhibitors of AChE with values of Ki = 19.0 +/- 0.9 microM for (S)-3 and 50 +/- 2 microM for (R)-3, respectively [22].

Analytical, diagnostic and therapeutic context of (R)-beta-Hydroxybutanoic acid

  • The first method is based on online determination of NaOH consumption rates necessary to neutralize 3-hydroxybutyric acid (3HB) and/or 3HB oligomers produced during the hydrolysis reaction and requires a pH-stat apparatus equipped with a software-controlled microliter pump for rapid and accurate titration [23].
  • The progress of the resolution was followed by chiral HPLC and the absolute stereochemistry of the two enantiomers determined by comparison of their specific rotations with that of (R)-3 synthesized from enantiomerically pure (R)-1-O-benzylglycerol [24].


  1. Proof for a nonproteinaceous calcium-selective channel in Escherichia coli by total synthesis from (R)-3-hydroxybutanoic acid and inorganic polyphosphate. Das, S., Lengweiler, U.D., Seebach, D., Reusch, R.N. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  2. Chiral compounds from bacterial polyesters: sugars to plastics to fine chemicals. Lee, S.Y., Lee, Y., Wang, F. Biotechnol. Bioeng. (1999) [Pubmed]
  3. Accumulation of poly (3-hydroxybutyric acid) by some soil Streptomyces. Manna, A., Banerjee, R., Paul, A.K. Curr. Microbiol. (1999) [Pubmed]
  4. Identification and characterization of two polyhydroxyalkanoate biosynthesis loci in Pseudomonas sp. strain 3Y2. Delamarre, S.C., Chang, H.J., Batt, C.A. Appl. Microbiol. Biotechnol. (2005) [Pubmed]
  5. Growth-associated production and characterization of poly (3-hydroxybutyric acid) of Azotobacter beijerinckii DAR-102. Manna, A., Paul, A.K. Indian J. Exp. Biol. (2003) [Pubmed]
  6. Induction of fetal hemoglobin in the presence of increased 3-hydroxybutyric acid associated with beta-ketothiolase deficiency. Galanello, R., Cao, A., Olivieri, N. N. Engl. J. Med. (1994) [Pubmed]
  7. Hypermetabolism of fat in v1a vasopressin receptor knockout mice. Hiroyama, M., Aoyagi, T., Fujiwara, Y., Birumachi, J., Shigematsu, Y., Kiwaki, K., Tasaki, R., Endo, F., Tanoue, A. Mol. Endocrinol. (2007) [Pubmed]
  8. Syntheses, calcium channel agonist-antagonist modulation activities, nitric oxide release, and voltage-clamp studies of 2-nitrooxyethyl 1,4-dihydro- 2,6-dimethyl-3-nitro-4-(2-trifluoromethylphenyl)pyridine-5-carboxylate enantiomers. Shan, R., Howlett, S.E., Knaus, E.E. J. Med. Chem. (2002) [Pubmed]
  9. Nonapeptide analogues containing (R)-3-hydroxybutanoate and beta-homoalanine oligomers: synthesis and binding affinity to a class I major histocompatibility complex protein. Poenaru, S., Lamas, J.R., Folkers, G., López de Castro, J.A., Seebach, D., Rognan, D. J. Med. Chem. (1999) [Pubmed]
  10. Metabolic engineering of Escherichia coli for production of enantiomerically pure (R)-(--)-hydroxycarboxylic acids. Lee, S.Y., Lee, Y. Appl. Environ. Microbiol. (2003) [Pubmed]
  11. Biochemical and molecular characterization of the polyhydroxybutyrate depolymerase of Comamonas acidovorans YM1609, isolated from freshwater. Kasuya, K., Inoue, Y., Tanaka, T., Akehata, T., Iwata, T., Fukui, T., Doi, Y. Appl. Environ. Microbiol. (1997) [Pubmed]
  12. Enzymatic synthesis of (-)- and (+)-acetoxyhexamides and (-)- and (+)-hydroxyhexamides. Akita, H., Kurashima, K., Nozawa, M., Kawana, T., Hirayama, K., Seri, K., Imamura, Y. Chem. Pharm. Bull. (1999) [Pubmed]
  13. Synthesis and transporter binding properties of (R)-2 beta, 3 beta- and (R)-2 alpha, 3 alpha-diaryltropanes. Jiang, S., Chang, A.C., Abraham, P., Kuhar, M.J., Carroll, F.I. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  14. Chemiluminescence of bovine polymorphonuclear leucocytes during the periparturient period and relation with metabolic markers and bovine pregnancy-associated glycoprotein. Hoeben, D., Monfardini, E., Opsomer, G., Burvenich, C., Dosogne, H., De Kruif, A., Beckers, J.F. J. Dairy Res. (2000) [Pubmed]
  15. Classification of abomasal displacement in cows according to histopathology of the liver and clinical chemistry. Komatsu, Y., Itoh, N., Taniyama, H., Kitazawa, T., Yokota, H., Koiwa, M., Ohtsuka, H., Terasaki, N., Maeno, K., Mizoguchi, M., Takeuchi, Y., Tanigawa, M., Nakamura, T., Watanabe, H., Matsuguchi, Y., Kukino, T., Honma, A. Journal of veterinary medicine. A, Physiology, pathology, clinical medicine. (2002) [Pubmed]
  16. Hypothalamic neuronal activity responses to 3-hydroxybutyric acid, an endogenous organic acid. Minami, T., Shimizu, N., Duan, S., Oomura, Y. Brain Res. (1990) [Pubmed]
  17. Effect of dietary protein on pyrimidine-metabolizing enzymes in rats. Kaneko, M., Fujimoto, S., Kikugawa, M., Kontani, Y., Tamaki, N. J. Nutr. Sci. Vitaminol. (1991) [Pubmed]
  18. Stimulation of ammonia production from glutamine by intraluminal glucose in small intestine of dogs. Weber, F.L., Veach, G., Friedman, D.W. Am. J. Physiol. (1982) [Pubmed]
  19. alpha-amylase inhibitor increases plasma 3-hydroxybutyric acid in food-restricted rats. Doi, T., Yoshimatsu, H., Katsuragi, I., Kurokawa, M., Takahashi, H., Motoshio, A., Sakata, T. Experientia (1995) [Pubmed]
  20. Active interaction of human A375 melanoma cells with the lymphatics in vivo. Papoutsi, M., Siemeister, G., Weindel, K., Tomarev, S.I., Kurz, H., Schächtele, C., Martiny-Baron, G., Christ, B., Marmé, D., Wilting, J. Histochem. Cell Biol. (2000) [Pubmed]
  21. (R)- and (S)-5,6,7,8-tetrahydro-1-hydroxy-N,N-dipropyl-9H-benzocyclohepten- 8-ylamine. Stereoselective interactions with 5-HT1A receptors in the brain. Liu, Y., Mellin, C., Björk, L., Svensson, B., Csöregh, I., Helander, A., Kenne, L., Andén, N.E., Hacksell, U. J. Med. Chem. (1989) [Pubmed]
  22. Change in the mode of inhibition of acetylcholinesterase by (4-nitrophenyl)sulfonoxyl derivatives of conformationally constrained choline analogues. Savle, P.S., Medhekar, R.A., Kelley, E.L., May, J.G., Watkins, S.F., Fronczek, F.R., Quinn, D.M., Gandour, R.D. Chem. Res. Toxicol. (1998) [Pubmed]
  23. Assay of poly(3-hydroxybutyrate) depolymerase activity and product determination. Gebauer, B., Jendrossek, D. Appl. Environ. Microbiol. (2006) [Pubmed]
  24. 2-Hydroxymethyl-1,4-dioxane: synthesis, resolution and determination of the absolute configurations of the enantiomers. Pallavicini, M., Valoti, E., Villa, L. Enantiomer. (2001) [Pubmed]
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