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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:22:04 UTC
HMDB IDHMDB00357
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxybutyric acid
Description3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-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. Blood levels of 3-Hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391 ).
Structure
Thumb
Synonyms
ValueSource
(1)-3-Hydroxybutyric acidChEBI
3 HBAChEBI
3-HydroxybuttersaeureChEBI
3-OH-Butyric acidChEBI
beta-Hydroxy-N-butyric acidChEBI
beta-Hydroxybutanoic acidChEBI
beta-HydroxybuttersaeureChEBI
beta-Hydroxybutyric acidChEBI
BHBAChEBI
DL-beta-Hydroxybutyric acidChEBI
(1)-3-HydroxybutyrateGenerator
3-HydroxybutanoateGenerator
3-OH-ButyrateGenerator
b-Hydroxy-N-butyrateGenerator
b-Hydroxy-N-butyric acidGenerator
beta-Hydroxy-N-butyrateGenerator
β-hydroxy-N-butyrateGenerator
β-hydroxy-N-butyric acidGenerator
b-HydroxybutanoateGenerator
b-Hydroxybutanoic acidGenerator
beta-HydroxybutanoateGenerator
β-hydroxybutanoateGenerator
β-hydroxybutanoic acidGenerator
b-HydroxybuttersaeureGenerator
β-hydroxybuttersaeureGenerator
b-HydroxybutyrateGenerator
b-Hydroxybutyric acidGenerator
beta-HydroxybutyrateGenerator
β-hydroxybutyrateGenerator
β-hydroxybutyric acidGenerator
DL-b-HydroxybutyrateGenerator
DL-b-Hydroxybutyric acidGenerator
DL-beta-HydroxybutyrateGenerator
DL-β-hydroxybutyrateGenerator
DL-β-hydroxybutyric acidGenerator
3-Hydroxy-butanoateHMDB
3-Hydroxy-butanoic acidHMDB
3-Hydroxy-butyrateHMDB
3-Hydroxy-butyric acidHMDB
3-HydroxybutyrateHMDB
BiopolHMDB
DL-3-HydroxybutyrateHMDB
DL-3-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name3-hydroxybutanoic acid
Traditional Name3 hydroxybutyrate
CAS Registry Number300-85-6
SMILES
CC(O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyInChIKey=WHBMMWSBFZVSSR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility444 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility539.0 mg/mLALOGPS
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m3·mol-1ChemAxon
Polarizability10.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-92be5c49a099fe1d9865View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-01ot-1920000000-c93138bf9d35643fef30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-8900000000-e632e14fb4be28bdb786View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-1900000000-e192caba63f034040624View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b31View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822cView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Liver
  • Neuron
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified60.0 +/- 20.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified40.0 +/- 10.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified323.0 +/- 29.0 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified50.0 (0.0-100.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified100.0 +/- 90.0 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified565.0 +/- 255.0 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified36.0 (13.0-95.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified76.9 +/- 66.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified180.0 (22.0-700.0) uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified1300 (1200-1400) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified34 +/- 31 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified50.0 (4.0 - 96.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified46.4 +/- 23.9 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified48.0 +/- 48.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified22.0932 +/- 9.606 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified5.00 +/- 4.25 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified2.64 +/- 1.83 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified3.22 +/- 2.77 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.88 +/- 4.26 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified16.44 +/- 19.52 uMAdult (>18 years old)FemaleNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified4.71 +/- 7.21 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified1.4-2.7 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified2.60 +/- 3.50 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified6.651 +/- 7.809 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified180.4 +/- 115.00 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified13.0 (1.0-27.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.4 +/- 1.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.7 (0-2.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<21.17 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified38.9 +/- 13.9 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified32.3 +/- 8.7 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified1.4-2.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.6 (1.3-6.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.0 (0.5-9.8) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified1.4 (0.1-2.7) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified1.3 (0.1-5.8) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified29.712 +/- 14.532 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.62 (0.0-12.09) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.24 (0.0-17.6) umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified2.0 (0.6-5.6) umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified235.0 +/- 17.0 uMAdult (>18 years old)FemaleObesity details
BloodDetected and Quantified35.1 +/- 33.9 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Oesophageal cancer
details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
BloodDetected and Quantified35.5 +/- 92.2 uMAdult (>18 years old)Both
Diabetes
details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Pancreatic
details
BloodDetected and Quantified0.0056 (0.0043-0.006) uMAdult (>18 years old)BothDiabetic ketoacidosis details
Cellular CytoplasmDetected and Quantified2600 (2500-2700) uMAdult (>18 years old)BothAnoxia details
SalivaDetected and Quantified5.04 +/- 3.02 uMAdult (>18 years old)BothTooth alignment disorders
    • Sugimoto et al. (...
details
SalivaDetected and Quantified6.62 +/- 0.72 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified6.37 +/- 1.75 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified24.25 +/- 32.08 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified35.352 +/- 40.756 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified30.883 +/- 22.266 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified74.311 +/- 155.898 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Anoxia
  1. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [8579834 ]
Diabetes mellitus type 2
  1. del Carmen Crespillo M, Olveira G, de Adana MS, Rojo-Martinez G, Garcia-Aleman J, Olvera P, Soriguer F, Munoz A: Metabolic effects of an enteral nutrition formula for diabetes: comparison with standard formulas in patients with type 1 diabetes. Clin Nutr. 2003 Oct;22(5):483-7. [14512036 ]
Obesity
  1. Vice E, Privette JD, Hickner RC, Barakat HA: Ketone body metabolism in lean and obese women. Metabolism. 2005 Nov;54(11):1542-5. [16253646 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021797
KNApSAcK IDNot Available
Chemspider ID428
KEGG Compound IDC01089
BioCyc IDCPD-335
BiGG IDNot Available
Wikipedia Link3-Hydroxybutyric acid
NuGOwiki LinkHMDB00357
Metagene LinkHMDB00357
METLIN ID125
PubChem Compound441
PDB IDNot Available
ChEBI ID20067
References
Synthesis ReferenceYang, Wenling; Ma, Peisheng; Wang, Jianing; Wang, Chunfang; Li, Haixia. Study on the process of chemical synthesis of 3-hydroxybutyric acid. Huaxue Gongcheng (Xi'an, China) (2002), 30(5), 74-78.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [11043913 ]
  2. 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. [11701757 ]
  3. 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. [12149510 ]
  4. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [2026685 ]
  5. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
  6. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [8579834 ]
  7. Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. [9693263 ]
  8. Frenkel G, Peterson RN, Freund M: Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. Fertil Steril. 1975 Feb;26(2):144-7. [1126459 ]
  9. Abrahamsson K, Eriksson BO, Holme E, Jodal U, Jonsson A, Lindstedt S: Pivalic acid-induced carnitine deficiency and physical exercise in humans. Metabolism. 1996 Dec;45(12):1501-7. [8969283 ]
  10. Teresinski G, Buszewicz G, Madro R: The influence of ethanol on the level of ketone bodies in hypothermia. Forensic Sci Int. 2002 Jun 25;127(1-2):88-96. [12098531 ]
  11. Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. [15363641 ]
  12. Blomqvist G, Alvarsson M, Grill V, Von Heijne G, Ingvar M, Thorell JO, Stone-Elander S, Widen L, Ekberg K: Effect of acute hyperketonemia on the cerebral uptake of ketone bodies in nondiabetic subjects and IDDM patients. Am J Physiol Endocrinol Metab. 2002 Jul;283(1):E20-8. [12067838 ]
  13. Krotkiewski M: Value of VLCD supplementation with medium chain triglycerides. Int J Obes Relat Metab Disord. 2001 Sep;25(9):1393-400. [11571605 ]
  14. Kamijo T, Indo Y, Souri M, Aoyama T, Hara T, Yamamoto S, Ushikubo S, Rinaldo P, Matsuda I, Komiyama A, Hashimoto T: Medium chain 3-ketoacyl-coenzyme A thiolase deficiency: a new disorder of mitochondrial fatty acid beta-oxidation. Pediatr Res. 1997 Nov;42(5):569-76. [9357925 ]
  15. Geary N, Grotschel H, Scharrer E: Blood metabolites and feeding during postinsulin hypophagia. Am J Physiol. 1982 Sep;243(3):R304-11. [7051864 ]
  16. Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [3884391 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02338
Molecular weight:
38156.77
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