(R)-3-Hydroxybutyric acid
(R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. 3-hydroxybutyric acid, or beta-hydroxybutyrate, is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circliating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. It can also be used for the synthesis of biodegradable plastics (Wikipedia).
Structure for HMDB00011 ((R)-3-Hydroxybutyric acid)
C4H8O3
104.1045
104.047344122
(3R)-3-hydroxybutanoic acid
(-)-3-hydroxybutyric acid
625-72-9
WHBMMWSBFZVSSR-GSVOUGTGSA-N
This compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Chemical entities
Organic compounds
Organic acids and derivatives
Hydroxy acids and derivatives
Beta hydroxy acids and derivatives
Aliphatic acyclic compounds
Detected and Quantified
Not Available
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-1900000000-b34932b6f2ee5bca9697View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9100000000-cdbb3586477ed705b4d7View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-022ab74e163dd752d054View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-18a18150fcc1dfee58cfView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e8d8003bcda8aa818d4eView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0006-9000000000-187f6a4024ca6e901188View in MoNA
LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-0a4i-9100000000-79f60e90c0ce32d976b3View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
Diabetes
Diabetes
Diabetes
Diabetes
Meningitis
Diabetes
- Sheikh-Ali M, Karon BS, Basu A, Kudva YC, Mliler LA, Xu J, Schwenk WF, Miles JM: Can serum beta-hydroxybutyrate be used to diagnose diabetic ketoacidosis? Diabetes Care. 2008 Apr;31(4):643-7. doi: 10.2337/dc07-1683. Epub 2008 Jan 9. [PubMed:18184896 ]
- Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jli;6(4):405-11. [PubMed:15982426 ]
- Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid mliti-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
- Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed:15627241 ]
Not Available
Not Available
Not Available
Not Available
FDB021869
Not Available
83181
C01089
CPD-335
36784
Not Available
HMDB00011
HMDB00011
Not Available
92135
3HR
17066
Product: Deoxycytidine triphosphate
- Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. [PubMed:11043913 ]
- Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. [PubMed:11701757 ]
- Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. [PubMed:12149510 ]
- Raunio RP, Leivo PV, Kuusinen AM: Bioluminescent assay of D-3-hydroxybutyrate in serum. J Biolumin Chemilumin. 1986 Jun;1(1):11-4. [PubMed:3503522 ]
- (). Bernardi, R. et al., Chem. Commun., 1984, 460, (resoln). .
- (). Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 994-995, (Et ester). .
- (). Fenaroli's Handbook of Flavor Ingredients, 3rd edn., (ed. Burdock, G.A.), CRC Press, 1995, 1, 238, (Et ester). .
- (). Forsyth, W.G.C. et al., Nature (London), 1958, 182, 800, (isol). .
- (). Gottschalk, G. et al., Nature (London), 1965, 205, 308. .
- (). Krajewski, D. et al., Phytochemistry, 1997, 45, 1627, (ester glucosides). .
- (). Levene, P.A. et al., J. Biol. Chem., 1926, 68, 418, (abs config). .
- (). Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MEF500 MKP250. .
- (). Marchessault, R.H. et al., Makromol. Chem., Macromol. Symp., 1988, 19, 235, (rev, polymers). .
- (). Muller, H.-M. et al., Angew. Chem., Int. Ed., 1993, 32, 477, (rev, polymer). .
- (). Org. Synth., 1993, 71, 39, (synth, acid, Meester, pmr, ir). .
- (). Quang DN, Hashimoto T, Toyota M, Asakawa Y. Occurrence of a high concentration of spider pheromones in the ascomycete fungus Hypoxylon truncatum. J Nat Prod. 2003 Dec;66(12):1613-4.. .
- (). Schulz S, Toft S. Identification of a sex pheromone from a spider. Science. 1993 Jun 11;260(5114):1635-7.. .
- (). Seebach, D. et al., Helv. Chim. Acta, 1982, 65, 495-503, (esters, synth). .
- (). Seebach, D. et al., Helv. Chim. Acta, 1988, 71, 155, (synth, dimer). .
- (). Wipf, B. et al., Helv. Chim. Acta, 1983, 66, 485. .
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Not Available
- Gene Name:
- BDH1
- Uniprot ID:
- Q02338
- Molecular weight:
- 38156.77
Reactions
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
- Gene Name:
- BDH2
- Uniprot ID:
- Q9BUT1
- Molecular weight:
- 26723.57
Reactions
- General function:
- Involved in catalytic activity
- Specific function:
- Not Available
- Gene Name:
- DKFZp434G1411
- Uniprot ID:
- Q9NT06
- Molecular weight:
- 16899.1
References
- Gibson KM, Lee CF, Kamali V, Johnston K, Beaudet AL, Craigen WJ, Powell BR, Schwartz R, Tsai MY, Tuchman M: 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency as detected by radiochemical assay in cell extracts by thin-layer chromatography, and identification of three new cases. Clin Chem. 1990 Feb;36(2):297-303. [PubMed:2302772 ]