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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2018-05-20 06:59:22 UTC
HMDB IDHMDB0003156
Secondary Accession Numbers
  • HMDB0003692
  • HMDB03156
  • 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.
Structure
Thumb
Synonyms
ValueSource
2,3-Butylene glycolChEBI
2,3-DihydroxybutaneChEBI
Dimethylene glycolChEBI
Dimethylethylene glycolChEBI
Pseudobutylene glycolChEBI
Sym-dimethylethylene glycolChEBI
2,3-ButandiolHMDB
2,3-ButanodiolHMDB
Butane-2,3-diolHMDB
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
SMILES
CC(O)C(C)O
InChI Identifier
InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3
InChI KeyOWBTYPJTUOEWEK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
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
PropertyValueSource
Water Solubility603 g/LALOGPS
logP-0.59ALOGPS
logP-0.38ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.39 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-e110e7ce89cc64b78ca2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-39d2dfc0a50d8ba018c7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-e110e7ce89cc64b78ca2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-39d2dfc0a50d8ba018c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cc27e53ef044f7cb15a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9520000000-fa7488838e20f2dd123bView in MoNA
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, Positivesplash10-0006-9000000000-373d8ab05d8ca30b9936View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-c995422d63c292e20b8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5639537d59074e5a4a6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-aa5e86f920a11ea2d749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cef0995334342db934baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-c4f65aef56394c6d3a25View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Platelet
  • Spleen
  • Testes
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.8 +/- 7.5 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified100.0 (5.0-211.0) uMAdult (>18 years old)Both
Cirrhosis
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Cirrhosis
  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 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011934
KNApSAcK IDNot Available
Chemspider ID21106093
KEGG Compound IDC00265
BioCyc IDCPD-346
BiGG ID34442
Wikipedia Link2,3-Butanediol
METLIN ID104
PubChem Compound262
PDB IDNot Available
ChEBI ID62064
References
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 ]

Enzymes

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:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3