3-Hydroxydodecanoic acid (CHEM022830)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:55:41 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022830
Identification
Common Name3-Hydroxydodecanoic acid
ClassSmall Molecule
DescriptionA medium-chain fatty acid that is the 3-hydroxylated derivative of lauric acid; associated with fatty acid metabolic disorders.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hydroxy-dodecanoic acidChEBI
3-OH Dodecanoic acidChEBI
3-OH Lauric acidChEBI
beta-Hydroxydodecanoic acidChEBI
beta-Hydroxylauric acidChEBI
beta-OH Dodecanoic acidChEBI
beta-OH Lauric acidChEBI
3-Hydroxy-dodecanoateGenerator
3-OH DodecanoateGenerator
3-OH LaateGenerator
3-OH Laic acidGenerator
b-HydroxydodecanoateGenerator
b-Hydroxydodecanoic acidGenerator
beta-HydroxydodecanoateGenerator
Β-hydroxydodecanoateGenerator
Β-hydroxydodecanoic acidGenerator
b-HydroxylaateGenerator
b-Hydroxylaic acidGenerator
beta-HydroxylaateGenerator
beta-Hydroxylaic acidGenerator
Β-hydroxylaateGenerator
Β-hydroxylaic acidGenerator
b-OH DodecanoateGenerator
b-OH Dodecanoic acidGenerator
beta-OH DodecanoateGenerator
Β-OH dodecanoateGenerator
Β-OH dodecanoic acidGenerator
b-OH LaateGenerator
b-OH Laic acidGenerator
beta-OH LaateGenerator
beta-OH Laic acidGenerator
Β-OH laateGenerator
Β-OH laic acidGenerator
3-HydroxydodecanoateGenerator
(RS)-3-HydroxylaurateHMDB
(RS)-3-Hydroxylauric acidHMDB
11:0(3-OH)HMDB
3-HydroxylaurateHMDB
3-Hydroxylauric acidHMDB
b-HydroxylaurateHMDB
b-Hydroxylauric acidHMDB
beta-HydroxylaurateHMDB
DL-b-HydroxydodecanoateHMDB
DL-b-Hydroxydodecanoic acidHMDB
DL-beta-HydroxydodecanoateHMDB
DL-beta-Hydroxydodecanoic acidHMDB
3-Hydroxydodecanoic acid, (S)-isomerHMDB
3-Hydroxydodecanoic acid, (R)-isomerHMDB
3-Hydroxydodecanoic acid, ion (1-)HMDB
3-Hydroxydodecanoic acid, monosilver (1+) salt, (R)-isomerHMDB
3-Hydroxydodecanoic acid, (+-)-isomerHMDB
3-Hydroxydodecanoic acid, ion (1-), (+-)-isomerHMDB
3-Hydroxydodecanoic acidMeSH
Chemical FormulaC12H24O3
Average Molecular Mass216.317 g/mol
Monoisotopic Mass216.173 g/mol
CAS Registry Number1883-13-2
IUPAC Name3-hydroxydodecanoic acid
Traditional Name3-hydroxydodecanoic acid
SMILESCCCCCCCCCC(O)CC(O)=O
InChI IdentifierInChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)
InChI KeyMUCMKTPAZLSKTL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.2 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-5930000000-267beffaa56f4c3885abSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-5930000000-267beffaa56f4c3885abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-9124202b1866ea2a0248Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9042000000-0d213d881baf293e004cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0aor-9050000000-f8825f9349ee9a2ec34eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-3d142f4358076fbe5192Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-54e9a813b1c73a4dee86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-7b771d914431e867cfe1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-3900000000-86799379f8d5d9fc2b80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-a1eb59a8d26b740ed683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1980000000-24c85a09e6439494d6ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0q2a-3910000000-0fec6c4e725d928fbb82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-071241699a72f84de36aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000387
FooDB IDFDB022005
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5376
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID85026
ChEBI ID36206
PubChem Compound ID94216
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11948802
2. Iwata, Tsutomu; Iwamoto, Osamu; Sugiyama, Haruhiko. Process for preparing b-hydroxy fatty acid. Eur. Pat. Appl. (1990), 6 pp.
3. Chickos JS, Way BA, Wilson J, Shaharuzzaman M, Laird J, Landt M: Analysis of 3-hydroxydodecanedioic acid for studies of fatty acid metabolic disorders: preparation of stable isotope standards. J Clin Lab Anal. 2002;16(2):115-20.
4. Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55.
5. Jones PM, Moffitt M, Joseph D, Harthcock PA, Boriack RL, Ibdah JA, Strauss AW, Bennett MJ: Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid. Clin Chem. 2001;47(7):1190-4.
6. Ktsoyan ZA, Beloborodova NV, Sedrakyan AM, Osipov GA, Khachatryan ZA, Kelly D, Manukyan GP, Arakelova KA, Hovhannisyan AI, Olenin AY, Arakelyan AA, Ghazaryan KA, Aminov RI: Profiles of Microbial Fatty Acids in the Human Metabolome are Disease-Specific. Front Microbiol. 2011 Jan 20;1:148. doi: 10.3389/fmicb.2010.00148. eCollection 2010.