3-Hydroxyoctanoic acid (CHEM035282)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:37:58 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035282
Identification
Common Name3-Hydroxyoctanoic acid
ClassSmall Molecule
DescriptionAn 8-carbon, beta-hydroxy fatty acid which may be a marker for primary defects of beta-hydroxy fatty acid metabolism. Repeating unit of poly(3-hydroxyoctanoic acid), a biopolymer used by numerous bacterial species as carbon and energy reserves.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hydroxy-octanoic acidChEBI
3-Hydroxycaprylic acidChEBI
3-OH Octanoic acidChEBI
3-OH-Caprylic acidChEBI
3HOChEBI
beta-Hydroxycaprylic acidChEBI
beta-Hydroxyoctanoic acidChEBI
beta-OH-Caprylic acidChEBI
beta-OH-Octanoic acidChEBI
3-Hydroxy-octanoateGenerator
3-HydroxycaprylateGenerator
3-OH OctanoateGenerator
3-OH-CaprylateGenerator
b-HydroxycaprylateGenerator
b-Hydroxycaprylic acidGenerator
beta-HydroxycaprylateGenerator
Β-hydroxycaprylateGenerator
Β-hydroxycaprylic acidGenerator
b-HydroxyoctanoateGenerator
b-Hydroxyoctanoic acidGenerator
beta-HydroxyoctanoateGenerator
Β-hydroxyoctanoateGenerator
Β-hydroxyoctanoic acidGenerator
b-OH-CaprylateGenerator
b-OH-Caprylic acidGenerator
beta-OH-CaprylateGenerator
Β-OH-caprylateGenerator
Β-OH-caprylic acidGenerator
b-OH-OctanoateGenerator
b-OH-Octanoic acidGenerator
beta-OH-OctanoateGenerator
Β-OH-octanoateGenerator
Β-OH-octanoic acidGenerator
3-HydroxyoctanoateGenerator
(+/-)-3-hydroxyoctanoateHMDB
(+/-)-3-hydroxyoctanoic acidHMDB
3-Hydroxy caprylic acidHMDB
3-Hydroxyoctanoic acid homopolymerHMDB
8:0(3-OH)HMDB
Poly-3-hydroxyoctanoateHMDB
Poly-3-hydroxyoctanoic acidHMDB
3-Hydroxyoctanoic acid, (S)-isomerHMDB
3-Hydroxy caprylateHMDB
3-Hydroxyoctanoic acidMeSH
Chemical FormulaC8H16O3
Average Molecular Mass160.211 g/mol
Monoisotopic Mass160.110 g/mol
CAS Registry Number14292-27-4
IUPAC Name3-hydroxyoctanoic acid
Traditional Name(+/-)-3-hydroxyoctanoic acid
SMILESCCCCCC(O)CC(O)=O
InChI IdentifierInChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyNDPLAKGOSZHTPH-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 Solubility13.6 g/LALOGPS
logP1.44ALOGPS
logP1.47ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.79 m³·mol⁻¹ChemAxon
Polarizability18.14 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)splash10-00ov-5920000000-2c7ce12b4e2e186a597fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ov-5920000000-2c7ce12b4e2e186a597fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-9100000000-86a1d77a8518a5914fd9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ri-9350000000-f1efc144e4aa8ba19a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-5e3edbe20a72bc04aee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-8900000000-64d2de5f37ff774bede7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-3532ef1933d1504375ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-65eeb84e30928c5f437aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aov-7900000000-6f869841cb09d5b95b79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-823bb7a721ecff6253b5Spectrum
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 IDHMDB0001954
FooDB IDFDB022761
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link3-Hydroxyoctanoic acid
Chemspider ID24791
ChEBI ID37098
PubChem Compound ID26613
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=18422622
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19047387
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3168281
4. Tahara, Satoshi; Suzuki, Yumiko; Mizutani, Junya. Fungal metabolism of a,b-unsaturated carboxylic acids. Part III. Fungal metabolism of trans-2-octenoic acid. Agricultural and Biological Chemistry (1977), 41(9), 1643-50.
5. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5.
6. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82.
7. Jones PM, Butt Y, Bennett MJ: Accumulation of 3-hydroxy-fatty acids in the culture medium of long-chain L-3-hydroxyacyl CoA dehydrogenase (LCHAD) and mitochondrial trifunctional protein-deficient skin fibroblasts: implications for medium chain triglyceride dietary treatment of LCHAD deficiency. Pediatr Res. 2003 May;53(5):783-7. Epub 2003 Mar 5.
8. Montgomery JA, Mamer OA, Colle E: Profiles in altered metabolism. IV--Induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat. Biomed Environ Mass Spectrom. 1989 Jun;18(6):416-23.
9. Kelley RI, Morton DH: 3-Hydroxyoctanoic aciduria: identification of a new organic acid in the urine of a patient with non-ketotic hypoglycemia. Clin Chim Acta. 1988 Jun 30;175(1):19-26.