Record Information
Version1.0
Creation date2015-05-07 18:46:39 UTC
Update date2018-01-25 19:46:45 UTC
Primary IDFDB030186
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2-dihydroxy-5-(methylthio)pent-1-en-3-one
Description1,2-dihydroxy-3-keto-5-methylthiopentene, also known as acireductone or 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one, is a member of the class of compounds known as alpha-branched alpha,beta-unsaturated ketones. Alpha-branched alpha,beta-unsaturated ketones are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom. 1,2-dihydroxy-3-keto-5-methylthiopentene is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1,2-dihydroxy-3-keto-5-methylthiopentene can be found in a number of food items such as breakfast cereal, lettuce, rocket salad, and sea-buckthornberry, which makes 1,2-dihydroxy-3-keto-5-methylthiopentene a potential biomarker for the consumption of these food products. 1,2-dihydroxy-3-keto-5-methylthiopentene exists in all eukaryotes, ranging from yeast to humans.
CAS Number746507-19-7
Structure
Thumb
Synonyms
SynonymSource
1,2-Dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneChEBI
1,2-Dihydroxy-5-(methylsulphanyl)pent-1-en-3-oneGenerator
AcireductoneHMDB
1,2-Dihydroxy-3-keto-5-methylthiopentaneHMDB
1,2-Dihydroxy-3-keto-5-methylthiopentene anionHMDB
1,2-Dihydroxy-5-(methylthio)pent-1-en-3-oneHMDB
Predicted Properties
PropertyValueSource
Water Solubility8.75 g/LALOGPS
logP0.07ALOGPS
logP0.81ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.87 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H10O3S
IUPAC name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
InChI IdentifierInChI=1S/C6H10O3S/c1-10-3-2-5(8)6(9)4-7/h4,7,9H,2-3H2,1H3/b6-4-
InChI KeyCILXJJLQPTUUSS-XQRVVYSFSA-N
Isomeric SMILESCSCCC(=O)C(\O)=C\O
Average Molecular Weight162.207
Monoisotopic Molecular Weight162.035064876
Classification
Description belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-branched alpha,beta-unsaturated ketones
Alternative Parents
Substituents
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Vinylogous acid
  • Enone
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Ketone
  • Enediol
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9300000000-19a09fc38a4607410081View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-025c-9170000000-6b6fd50d76488524c888View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-523c47d24f3c45c4f285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07xs-9700000000-cbbc0baabd68adaf65adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c591ef1f6d20bddce525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-bd31c9d726fbcfa6d7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-4d0c04f4b382ef0d5b9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-96c889c8c6acb6410bf6View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference