Caprylic acid (T3D4594)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-09-05 17:11:58 UTC
Update Date2014-12-24 20:26:53 UTC
Accession NumberT3D4594
Identification
Common NameCaprylic acid
ClassSmall Molecule
DescriptionCaprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes.
Compound Type
  • Animal Toxin
  • Dye
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Heptanecarboxylate
1-Heptanecarboxylic acid
Caprylate
capryloate
Caprylsaeure
Emery 657
Enantic acid
Kaprylsaeure
Kortacid 0899
Lunac 8-95
Lunac 8-98
N-Caprylate
N-Caprylic acid
N-Octanoate
N-Octanoic acid
N-Octoate
N-Octoic acid
N-Octylate
N-Octylic acid
Neo-Fat 8
Neo-Fat 8S
octanoate
octanoic acid
Octic acid
octoic acid
Octylate
Octylic acid
Prifac 2901
Chemical FormulaC8H16O2
Average Molecular Mass144.211 g/mol
Monoisotopic Mass144.115 g/mol
CAS Registry Number124-07-2
IUPAC Nameoctanoic acid
Traditional Namecaprylic acid
SMILESCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChI KeyInChIKey=WWZKQHOCKIZLMA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Epidermis
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceOily colorless liquid.
Experimental Properties
PropertyValue
Melting Point16.5°C
Boiling Point239°C
Solubility789 mg/L (at 30°C)
LogP3.05
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde02014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-1920000000-1dc6ed976e003f99e23d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03kc-9000000000-74cfce03769b413139522017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uyi-0931100000-7668e36e436054042b5c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde02017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1920000000-1dc6ed976e003f99e23d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-9ecb4ccb46e89710f76a2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9100000000-8854c56056d8d34050872016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-062l-9100000000-67da39159980b9078fab2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0900000000-bb237630bedcee6145d12012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-2900000000-98284f50a271878c84812012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-5900000000-209fbbacd4996b9a770d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03kc-9000000000-74cfce03769b413139522012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e2c4dff10393086340f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-bbde8564b4e5543a636a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negativesplash10-0006-0900000000-d219a0c6559a4783fd812017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-e2c4dff10393086340f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-bbde8564b4e5543a636a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-0900000000-ca22ecd0b25fa371fc732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gvp-9100000000-58c00a2024ba0bae4ff42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-2505e6738cf5d58776542021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1ab4cdf8f74c933127432021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-ac7c80e50c93b8cc3af72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-d2694b5f89d8eaeb2ab12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f2b24072c91d8b0e40782016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-ad62d44e72f4dd1760ab2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7900000000-9c869b84815f21dffc7c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8a648d443695914e4792016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-9100000000-f5c38fdad70b324e75ac2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bee103956686b4840d1e2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-e7cbd036c8e80018c8252021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f2b048da6331570976c2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-cd31ca01a5fa6be86acb2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-682c215be5abe1fe87ed2021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureIngestion
Mechanism of ToxicityIt has been demonstrated that octanoic (OA) and decanoic (DA) acids compromise the glycolytic pathway and citric acid cycle functioning, increase oxygen consumption in the liver and inhibit some activities of the respiratory chain complexes and creatine kinase in rat brain (6, 7). These fatty acids were also shown to induce oxidative stress in the brain (8). Experiments suggest that OA and DA impair brain mitochondrial energy homeostasis that could underlie at least in part the neuropathology of MCADD. (9)
MetabolismThe enzyme MCAD (medium-chain acyl-CoA dehydrogenase) is responsible for the dehydrogenation step of fatty acids with chain lengths between 6 and 12 carbons as they undergo beta-oxidation in the mitochondria. Fatty acid beta-oxidation provides energy after the body has used up its stores of glucose and glycogen. This typically occurs during periods of extended fasting or illness when caloric intake is reduced, and energy needs are increased. Beta-oxidation of long chain fatty acids produces two carbon units, acetyl-CoA and the reducing equivalents NADH and FADH2. NADH and FADH2 enter the electron transport chain and are used to make ATP. Acetyl-CoA enters the Krebs Cycle and is also used to make ATP via the electron transport chain and substrate level phosphorylation. When the supply of acetyl-CoA (coming from the beta-oxidation of fatty acids) exceeds the capacity of the Krebs Cycle to metabolize acetyl-CoA, the excess acetyl-CoA molecules are converted to ketone bodies (acetoacetate and beta-hydroxybutyrate) by HMG-CoA synthase in the liver. Ketone bodies can also be used for energy especially by the brain and heart; in fact they become the main sources of energy for those two organs after day three of starvation. (Wikipedia)
Toxicity ValuesOral rat LD50: 10080 mg/kg. Intravenous mouse LD50: 600 mg/kg. Skin rabbit LD50: over 5000 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCaprylic acid is found naturally in the milk of various mammals, and as a minor constituent of coconut oil and palm kernel oil. It is also an endogenously produced metabolite found in the human body. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, animal care/veterinary facilities, industrial facilities, office buildings, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algaecide, bactericide, and fungicide in nurseries, greenhouses, garden centers, and interiorscapes on ornamentals. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids. The acid chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid. Caprylic acid has medical uses as a medium-chain triglyceride. Caprylic acid is also used in the treatment of some bacterial infections. Due to its relatively short chain length it has no difficulty in penetrating fatty cell wall membranes, hence its effectiveness in combating certain lipid-coated bacteria, such as Staphylococcus aureus and various species of Streptococcus. The octanoic acid breath test is used to measure gastric emptying. Some potential benefit is possible from administration of octanoic acid for patients with Essential tremor. Caprylic acid is taken as a dietary supplement. It is believed to suppress fungal infections within the gut, notably candida albicans infection. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsOctanoic (OA) and decanoic (DA) acids are the predominant metabolites accumulating in medium-chain acyl-CoA dehydrogenase (MCAD; E.C. 1.3.99.3) deficiency (MCADD), the most common inherited defect of fatty acid oxidation. Glycine and l-carnitine bind to these fatty acids giving rise to derivatives that also accumulate in this disorder. The clinical presentation typically occurs in early childhood but can occasionally be delayed until adulthood. The major features of the disease include hypoglycemia, vomiting, lethargy and encephalopathy after fasting, infection or other metabolic stressors. (9)
SymptomsMCADD presents in early childhood with hypoketotic hypoglycemia and liver dysfunction, often preceded by extended periods of fasting or an infection with vomiting. Infants who are exclusively breast-fed may present in this manner shortly after birth, due to poor feeding. In some individuals the first manifestation of MCADD may be sudden death following a minor illness. A number of individuals with MCADD may remain completely asymptomatic, provided they never encounter a situation that sufficiently stresses their metabolism. (Wikipedia)
TreatmentManagement of acute MCADD includes rapid correction of hypoglycemia, rehydration and treatment of the underlying infection or other stress factor. Current long-term therapy includes avoidance of fasting and a high carbohydrate low-fat diet, but it does not fully prevent the crises and the neurological alterations. (9)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04519
HMDB IDHMDB00482
PubChem Compound ID379
ChEMBL IDCHEMBL324846
ChemSpider ID370
KEGG IDC06423
UniProt IDNot Available
OMIM ID
ChEBI ID28837
BioCyc IDCPD-195
CTD IDNot Available
Stitch IDNot Available
PDB IDOCA
ACToR IDNot Available
Wikipedia LinkCaprylic acid
References
Synthesis Reference

William Elliott Bay, Joseph Norman Bernadino, George Frederick Klein, Yi Ren, Pingsheng Zhang, “METHODS FOR PRODUCING N-(8-[2-HYDROXYBENZOYL]-AMINO) CAPRYLIC ACID.” U.S. Patent US20080064890, issued March 13, 2008.

MSDSLink
General References
  1. Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. [12086718 ]
  2. Dieterle F, Muller-Hagedorn S, Liebich HM, Gauglitz G: Urinary nucleosides as potential tumor markers evaluated by learning vector quantization. Artif Intell Med. 2003 Jul;28(3):265-79. [12927336 ]
  3. Nair MK, Joy J, Venkitanarayanan KS: Inactivation of Enterobacter sakazakii in reconstituted infant formula by monocaprylin. J Food Prot. 2004 Dec;67(12):2815-9. [15633694 ]
  4. Habeeb AF, Francis RD: Preparation of human immunoglobulin by caprylic acid precipitation. Prep Biochem. 1984;14(1):1-17. [6718324 ]
  5. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
  6. Scholz R, Schwabe U, Soboll S: Influence of fatty acids on energy metabolism. 1. Stimulation of oxygen consumption, ketogenesis and CO2 production following addition of octanoate and oleate in perfused rat liver. Eur J Biochem. 1984 May 15;141(1):223-30. [6426957 ]
  7. Reis de Assis D, Maria Rde C, Borba Rosa R, Schuck PF, Ribeiro CA, da Costa Ferreira G, Dutra-Filho CS, Terezinha de Souza Wyse A, Duval Wannmacher CM, Santos Perry ML, Wajner M: Inhibition of energy metabolism in cerebral cortex of young rats by the medium-chain fatty acids accumulating in MCAD deficiency. Brain Res. 2004 Dec 24;1030(1):141-51. [15567346 ]
  8. Schuck PF, Ferreira GC, Moura AP, Busanello EN, Tonin AM, Dutra-Filho CS, Wajner M: Medium-chain fatty acids accumulating in MCAD deficiency elicit lipid and protein oxidative damage and decrease non-enzymatic antioxidant defenses in rat brain. Neurochem Int. 2009 Jul;54(8):519-25. doi: 10.1016/j.neuint.2009.02.009. Epub 2009 Feb 24. [19428797 ]
  9. Schuck PF, Ferreira Gda C, Tonin AM, Viegas CM, Busanello EN, Moura AP, Zanatta A, Klamt F, Wajner M: Evidence that the major metabolites accumulating in medium-chain acyl-CoA dehydrogenase deficiency disturb mitochondrial energy homeostasis in rat brain. Brain Res. 2009 Nov 3;1296:117-26. doi: 10.1016/j.brainres.2009.08.053. Epub 2009 Aug 21. [19703432 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available