Record Information
Version1.0
Creation date2010-04-08 22:09:25 UTC
Update date2019-11-26 03:04:27 UTC
Primary IDFDB010997
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2R,3R-Butanediol
Description(2R,3R)-2,3-Butanediol, also known as (R,R)-2,3-butylene glycol or (2R,3R)-butane-2,3-diol, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions (2R,3R)-2,3-Butanediol is an extremely weak basic (essentially neutral) compound (based on its pKa) (2R,3R)-2,3-Butanediol has been detected, but not quantified in, cocoa and cocoa products and herbs and spices. This could make (2R,3R)-2,3-butanediol a potential biomarker for the consumption of these foods.
CAS Number24347-58-8
Structure
Thumb
Synonyms
SynonymSource
(R,R)-(-)-Butane-2,3-diolChEBI
(R,R)-2,3-ButanediolChEBI
(R,R)-2,3-Butylene glycolChEBI
(-)-(2R,3R)-ButanediolHMDB
(-)-2,3-ButanediolHMDB
(2R,3R)-(-)-2,3-ButanediolHMDB
(2R,3R)-Butane-2,3-diolHMDB
L-(-)-2,3-ButanediolHMDB
Levo-2,3-butanediolHMDB
(R,R)-Butane-2,3-diolbiospider
2R,3R-Butanediolmanual
levo-2,3-Butanediolmanual
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
Polarizability9.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H10O2
IUPAC name(2R,3R)-butane-2,3-diol
InChI IdentifierInChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1
InChI KeyOWBTYPJTUOEWEK-QWWZWVQMSA-N
Isomeric SMILESC[C@@H](O)[C@@H](C)O
Average Molecular Weight90.121
Monoisotopic Molecular Weight90.068079564
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 53.31%; H 11.18%; O 35.51%DFC
Melting PointMp 19.7°DFC
Boiling PointBp10 77.5-77.6°DFC
Experimental Water SolubilityNot Available
Experimental logP0.88HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -13 (neat)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cc27e53ef044f7cb15a5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9520000000-fa7488838e20f2dd123bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-373d8ab05d8ca30b9936JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-c995422d63c292e20b8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5639537d59074e5a4a6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-aa5e86f920a11ea2d749JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cef0995334342db934baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-c4f65aef56394c6d3a25JSpectraViewer
ChemSpider ID196452
ChEMBL IDNot Available
KEGG Compound IDC03044
Pubchem Compound ID225936
Pubchem Substance IDNot Available
ChEBI ID16982
Phenol-Explorer IDNot Available
DrugBank IDDB02418
HMDB IDHMDB33007
CRC / DFC (Dictionary of Food Compounds) IDHBW83-K:FXZ78-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDBU3
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2,3-Butanediol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Ubiquitin-conjugating enzyme E2 D2UBE2D2P62837
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference