Record Information
Version1.0
Creation date2011-09-21 01:45:05 UTC
Update date2020-09-17 15:39:31 UTC
Primary IDFDB028796
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2-Dihydroxy-3-keto-5-methylthiopentene
Description1,2-Dihydroxy-3-keto-5-methylthiopentene, also known as 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one or acireductone, 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. 1,2-Dihydroxy-3-keto-5-methylthiopentene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Dihydroxy-3-keto-5-methylthiopentene exists in all living species, ranging from bacteria to humans. Outside of the human body, 1,2-Dihydroxy-3-keto-5-methylthiopentene has been detected, but not quantified in, several different foods, such as nopals, chayotes, mustard spinachs, pigeon pea, and red bell peppers. This could make 1,2-dihydroxy-3-keto-5-methylthiopentene a potential biomarker for the consumption of these foods.
CAS Number746507-19-7
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility8.75 g/LALOGPS
logP0.07ALOGPS
logP0.81ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-9300000000-19a09fc38a4607410081Spectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-025c-9170000000-6b6fd50d76488524c888Spectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-523c47d24f3c45c4f2852016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07xs-9700000000-cbbc0baabd68adaf65ad2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c591ef1f6d20bddce5252016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-bd31c9d726fbcfa6d7e12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-4d0c04f4b382ef0d5b9c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-96c889c8c6acb6410bf62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-7900000000-4e7dffabd3e521b59a332021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-9000000000-4dee6c63f979437272b02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9000000000-e4050047631669464d942021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-6f5f734e698f1dbf5d5c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-24View Spectrum
NMRNot Available
ChemSpider ID4575316
ChEMBL IDNot Available
KEGG Compound IDC15606
Pubchem Compound ID5462190
Pubchem Substance IDNot Available
ChEBI ID49252
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12134
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference