Record Information
Version1.0
Creation date2010-04-08 22:09:22 UTC
Update date2019-11-26 03:04:16 UTC
Primary IDFDB010907
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-3-Hydroxyoctanoic acid
Description(R)-3-Hydroxyoctanoic acid, also known as (R)-3-OH-caprylic acid or (3R)-3-hydroxy-octanoate, 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 (R)-3-Hydroxyoctanoic acid exists in all eukaryotes, ranging from yeast to plants to humans (R)-3-Hydroxyoctanoic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), fruits, and milk and milk products. This could make (R)-3-hydroxyoctanoic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-3-Hydroxyoctanoic acid.
CAS Number44987-72-6
Structure
Thumb
Synonyms
SynonymSource
(3R)-3-Hydroxy-octanoic acidChEBI
(R)-3-Hydroxycaprylic acidChEBI
(R)-3-OH Octanoic acidChEBI
(R)-3-OH-Caprylic acidChEBI
(R)-beta-Hydroxycaprylic acidChEBI
(R)-beta-Hydroxyoctanoic acidChEBI
(R)-beta-OH-Caprylic acidChEBI
(R)-beta-OH-Octanoic acidChEBI
(3R)-3-Hydroxy-octanoateGenerator
(R)-3-HydroxycaprylateGenerator
(R)-3-OH OctanoateGenerator
(R)-3-OH-CaprylateGenerator
(R)-b-HydroxycaprylateGenerator
(R)-b-Hydroxycaprylic acidGenerator
(R)-beta-HydroxycaprylateGenerator
(R)-Β-hydroxycaprylateGenerator
(R)-Β-hydroxycaprylic acidGenerator
(R)-b-HydroxyoctanoateGenerator
(R)-b-Hydroxyoctanoic acidGenerator
(R)-beta-HydroxyoctanoateGenerator
(R)-Β-hydroxyoctanoateGenerator
(R)-Β-hydroxyoctanoic acidGenerator
(R)-b-OH-CaprylateGenerator
(R)-b-OH-Caprylic acidGenerator
(R)-beta-OH-CaprylateGenerator
(R)-Β-OH-caprylateGenerator
(R)-Β-OH-caprylic acidGenerator
(R)-b-OH-OctanoateGenerator
(R)-b-OH-Octanoic acidGenerator
(R)-beta-OH-OctanoateGenerator
(R)-Β-OH-octanoateGenerator
(R)-Β-OH-octanoic acidGenerator
(R)-3-HydroxyoctanoateGenerator
(R)-β-hydroxycaprylateGenerator
(R)-β-hydroxycaprylic acidGenerator
(R)-β-hydroxyoctanoateGenerator
(R)-β-hydroxyoctanoic acidGenerator
(R)-β-OH-caprylateGenerator
(R)-β-OH-caprylic acidGenerator
(R)-β-OH-octanoateGenerator
(R)-β-OH-octanoic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H16O3
IUPAC name(3R)-3-hydroxyoctanoic acid
InChI IdentifierInChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m1/s1
InChI KeyNDPLAKGOSZHTPH-SSDOTTSWSA-N
Isomeric SMILES[H][C@@](O)(CCCCC)CC(O)=O
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 59.98%; H 10.07%; O 29.96%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -21 (c, 1.9 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-3-Hydroxyoctanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052o-9200000000-43d57763d2a30e89979bSpectrum
Predicted GC-MS(R)-3-Hydroxyoctanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ri-9350000000-f1efc144e4aa8ba19a72Spectrum
Predicted GC-MS(R)-3-Hydroxyoctanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-3-Hydroxyoctanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1900000000-e5cda5e57d0fb350dc6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-8900000000-206c3ff570d17b537e39Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c32a98aa8083b6459b4aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-9112efe71e9f56f43babSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-8900000000-f482349594658282b6e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9100000000-b0b3f7b33ed057654f96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zna-9400000000-ba19979661ce66d42c47Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-7a423069bad50c00a0fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-7c89cf68b731953f3797Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-3900000000-ef763a7f3b584b771412Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-9100000000-9b510a15a343a9e2d365Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-05f3a26a1fda3e795cbaSpectrum
NMRNot Available
ChemSpider ID4472286
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5312861
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10722
CRC / DFC (Dictionary of Food Compounds) IDDCC28-Q:FTT51-K
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Fatty acid synthaseFASNP49327
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference