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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2020-02-26 21:24:24 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. 2,3-Butanediol can also be found in Bacillus, Klebsiella and Serratia (PMID: 21272631 ).
Structure
Data?1582752264
Synonyms
ValueSource
2,3-Butylene glycolChEBI
2,3-DihydroxybutaneChEBI
Dimethylene glycolChEBI
Dimethylethylene glycolChEBI
Pseudobutylene glycolChEBI
Sym-dimethylethylene glycolChEBI
2,3-ButandiolHMDB
2,3-ButanodiolHMDB
D-2,3-Butane diolHMDB
2,3-Butylene glycol, (r*,r*)-isomerHMDB
2,3-Butylene glycol, (r*,r*,)-(+-)-isomerHMDB
2,3-Butylene glycol, R-(r*,r*)-isomerHMDB
2,3-Butylene glycol, (S-(r*,r*))-isomerHMDB
2,3-Butylene glycol, (r*,s*)-isomerHMDB
Butane-2,3-diolHMDB
2,3-ButanediolChEBI
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
Description 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-e110e7ce89cc64b78ca2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-39d2dfc0a50d8ba018c7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-e110e7ce89cc64b78ca2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-39d2dfc0a50d8ba018c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cc27e53ef044f7cb15a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9520000000-fa7488838e20f2dd123bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-a38d022475e970ac03d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dl-9000000000-c09bcb32a4424164b2b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p9-9000000000-7e0b3df968981c428a95Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0002-9000000000-f6fb3d0277c373b5e557Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positivesplash10-0002-9000000000-94dd097f8cd58f7a22e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-373d8ab05d8ca30b9936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-c995422d63c292e20b8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5639537d59074e5a4a6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-aa5e86f920a11ea2d749Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cef0995334342db934baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-c4f65aef56394c6d3a25Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Platelet
  • Spleen
  • Testis
  • 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 QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDDTT
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 ]
  17. Ji XJ, Huang H, Ouyang PK: Microbial 2,3-butanediol production: a state-of-the-art review. Biotechnol Adv. 2011 May-Jun;29(3):351-64. doi: 10.1016/j.biotechadv.2011.01.007. Epub 2011 Jan 24. [PubMed:21272631 ]

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