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Record Information
Creation Date2006-05-22 15:12:37 UTC
Update Date2017-03-02 21:27:11 UTC
Secondary Accession Numbers
  • HMDB03692
Metabolite Identification
Common Name2,3-Butanediol
Description2,3-Butanediol is an isomer of butanediol. The 2R,3R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms, in a process known as butanediol fermentation. 2,3-Butanediol fermentation is the anaerobic fermentation of glucose with 2,3-butanediol as one of the end products. The overall stoichiometry of the reaction is 2 pyruvate + NADH --> 2CO2 + 2,3-butanediol. Butanediol fermentation is typical for Enterobacter species or microbes found in the gut. 2,3-butanediol has been identified in the sera of alcoholics and it may be a specific marker of alcohol abuse (PMID: 6139706 ). In humans, 2,3-butanediol is oxidized to acetyl-CoA via acetoin. 2,3-Butanediol is also found in cocoa butter.
2,3-Butylene glycolChEBI
Dimethylene glycolChEBI
Dimethylethylene glycolChEBI
Pseudobutylene glycolChEBI
Sym-dimethylethylene glycolChEBI
D-2,3-Butane diolHMDB
2,3-Butylene glycol, (r*,r*)-isomerMeSH
2,3-Butylene glycol, (r*,r*,)-(+-)-isomerMeSH
2,3-Butylene glycol, R-(r*,r*)-isomerMeSH
2,3-Butylene glycol, (S-(r*,r*))-isomerMeSH
2,3-Butylene glycol, (r*,s*)-isomerMeSH
Chemical FormulaC4H10O2
Average Molecular Weight90.121
Monoisotopic Molecular Weight90.068079564
IUPAC Namebutane-2,3-diol
Traditional Name2,3-butanediol
CAS Registry Number513-85-9
InChI Identifier
Chemical Taxonomy
ClassificationNot classified
StatusDetected and Quantified
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.92HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility603.0 mg/mLALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.39 m3·mol-1ChemAxon
Polarizability9.87 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-a38d022475e970ac03d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dl-9000000000-c09bcb32a4424164b2b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p9-9000000000-7e0b3df968981c428a95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0002-9000000000-f6fb3d0277c373b5e557View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positivesplash10-0002-9000000000-94dd097f8cd58f7a22e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Platelet
  • Spleen
  • Testes
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified13.8 +/- 7.5 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified100.0 (5.0-211.0) uMAdult (>18 years old)Both
Associated Disorders and Diseases
Disease References
  1. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011934
KNApSAcK IDNot Available
Chemspider ID21106093
KEGG Compound IDC00265
BioCyc IDCPD-346
BiGG ID34442
Wikipedia LinkDithiothreitol
NuGOwiki LinkHMDB03156
Metagene LinkHMDB03156
PubChem Compound262
PDB IDNot Available
ChEBI ID62064
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohno S, Nakajima Y, Nakajin S: Triphenyltin and Tributyltin inhibit pig testicular 17beta-hydroxysteroid dehydrogenase activity and suppress testicular testosterone biosynthesis. Steroids. 2005 Aug;70(9):645-51. [PubMed:15899506 ]
  2. Plaisant F, Clippe A, Vander Stricht D, Knoops B, Gressens P: Recombinant peroxiredoxin 5 protects against excitotoxic brain lesions in newborn mice. Free Radic Biol Med. 2003 Apr 1;34(7):862-72. [PubMed:12654475 ]
  3. Wroblewski VJ: Mechanism of deiodination of 125I-human growth hormone in vivo. Relevance to the study of protein disposition. Biochem Pharmacol. 1991 Jul 25;42(4):889-97. [PubMed:1867644 ]
  4. Murray JI, Whitfield ML, Trinklein ND, Myers RM, Brown PO, Botstein D: Diverse and specific gene expression responses to stresses in cultured human cells. Mol Biol Cell. 2004 May;15(5):2361-74. Epub 2004 Mar 5. [PubMed:15004229 ]
  5. Paul BZ, Vilaire G, Kunapuli SP, Bennett JS: Concurrent signaling from Galphaq- and Galphai-coupled pathways is essential for agonist-induced alphavbeta3 activation on human platelets. J Thromb Haemost. 2003 Apr;1(4):814-20. [PubMed:12871420 ]
  6. Ueda N, Tsuboi K, Lambert DM: A second N-acylethanolamine hydrolase in mammalian tissues. Neuropharmacology. 2005 Jun;48(8):1079-85. [PubMed:15910884 ]
  7. Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
  8. Sakai A, Sakakibara R, Ishiguro M: Human chorionic gonadotropin-ricin A chain hybrid protein: a hormone analog for the study of signal transduction. J Biochem. 1989 Feb;105(2):275-80. [PubMed:2542238 ]
  9. Jin Y, Kim DK, Khil LY, Oh U, Kim J, Kwak J: Thimerosal decreases TRPV1 activity by oxidation of extracellular sulfhydryl residues. Neurosci Lett. 2004 Oct 21;369(3):250-5. [PubMed:15464274 ]
  10. Moshkin AV: [Stabilization of creatine kinase isoenzymes in the cerebrospinal fluid in cranio-cerebral trauma]. Lab Delo. 1989;(2):48-52. [PubMed:2467061 ]
  11. Chujor CS, Feingold KR, Elias PM, Holleran WM: Glucosylceramide synthase activity in murine epidermis: quantitation, localization, regulation, and requirement for barrier homeostasis. J Lipid Res. 1998 Feb;39(2):277-85. [PubMed:9507988 ]
  12. Sachs MK, Huang CM, Ost D, Jungkind DL: Failure of dithiothreitol and pronase to reveal a false-positive cryptococcal antigen determination in cerebrospinal fluid. Am J Clin Pathol. 1991 Sep;96(3):381-4. [PubMed:1877537 ]
  13. Herblin WF, Chiu AT, McCall DE, Ardecky RJ, Carini DJ, Duncia JV, Pease LJ, Wong PC, Wexler RR, Johnson AL, et al.: Angiotensin II receptor heterogeneity. Am J Hypertens. 1991 Apr;4(4 Pt 2):299S-302S. [PubMed:1854455 ]
  14. Cooper CA, Bury NR, Grosell M: The effects of pH and the iron redox state on iron uptake in the intestine of a marine teleost fish, gulf toadfish (Opsanus beta). Comp Biochem Physiol A Mol Integr Physiol. 2006 Mar;143(3):292-8. Epub 2006 Jan 20. [PubMed:16431145 ]
  15. Hermand P, Gane P, Huet M, Jallu V, Kaplan C, Sonneborn HH, Cartron JP, Bailly P: Red cell ICAM-4 is a novel ligand for platelet-activated alpha IIbbeta 3 integrin. J Biol Chem. 2003 Feb 14;278(7):4892-8. Epub 2002 Dec 10. [PubMed:12477717 ]
  16. Kuehnle J, Holzbaur J: 2,3-Butanediol in serum of alcoholics. Lancet. 1983 Dec 10;2(8363):1369-70. [PubMed:6139706 ]


General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
Uniprot ID:
Molecular weight: