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Capric acid (CHEM003730)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-11 05:15:59 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003730
Identification
Common NameCapric acid
ClassSmall Molecule
DescriptionCapric acid is a member of the series of fatty acids found in oils and animal fats. The names of Caproic, Caprylic, and Capric acids are all derived from the word caper (Latin: 'goat'). These are colorless light yellowish transparent oily liquids with unconfortable smells. These are used in organic synthesis, manufacture of perfume, medicine, lubricating grease, rubber and dye.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Antifungal Agent
  • Dye
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Nonanecarboxylic acidChEBI
10:0ChEBI
C10:0ChEBI
Caprinic acidChEBI
CH3-[CH2]8-COOHChEBI
DecanoateChEBI
Decoic acidChEBI
Decylic acidChEBI
DekansaeureChEBI
KaprinsaeureChEBI
N-Capric acidChEBI
N-Decanoic acidChEBI
N-Decoic acidChEBI
N-Decylic acidChEBI
1-NonanecarboxylateGenerator
CaprinateGenerator
Decanoic acidGenerator
DecoateGenerator
DecylateGenerator
N-CaprateGenerator
N-DecanoateGenerator
N-DecoateGenerator
N-DecylateGenerator
CaprateGenerator
CaprynateHMDB
Caprynic acidHMDB
Emery 659HMDB
Lunac 10-95HMDB
Lunac 10-98HMDB
Prifac 2906HMDB
Prifac 296HMDB
Decanoic acid, sodium saltHMDB
Sodium caprateHMDB
Sodium decanoateHMDB
FA(10:0)HMDB
Chemical FormulaC10H20O2
Average Molecular Mass172.265 g/mol
Monoisotopic Mass172.146 g/mol
CAS Registry Number334-48-5
IUPAC Namedecanoic acid
Traditional Namecapric acid
SMILESCCCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
InChI KeyGHVNFZFCNZKVNT-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
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Fatty Acid BiosynthesisSMP00456 map00061
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point31.9°C
Boiling Point268.7°C
Solubility61.8 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.095 g/LALOGPS
logP3.93ALOGPS
logP3.59ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability21.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2920000000-7f6721f01b80a790d544View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-052g-9200000000-71a57b0e200e46fb66edView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-076u-9000000000-96a2e9e00e464db3c086View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-017i-2920000000-7f6721f01b80a790d544View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-016r-1910000000-1cc1026f6f325d994ab4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-00g0-9300000000-c615f39c0b907a00f67cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-771e7907916bf05e6b10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-f1e000384728ee06f802View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-1900000000-42a901bb54546da030daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-83e77de04461ded1c4bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-f3190b828218d04d3cc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0000000910-e82208ed71b4a3735258View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0900000000-8c6cdf0491f51ba6ef26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-3afa642872e4450f0c49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-771e7907916bf05e6b10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-f1e000384728ee06f802View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-d5dbc60c65c1a7d34e2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-83e77de04461ded1c4bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f3190b828218d04d3cc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-0900000000-53ea38eb25eaea66d22aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0900000000-8c6cdf0491f51ba6ef26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0900000000-3afa642872e4450f0c49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-0a7f944302bce161f7e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-1900000000-b68efbceecf3433a9995View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-005a-9600000000-f2a54ed1a56ee9b7af77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-076u-9000000000-96a2e9e00e464db3c086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kf-0900100000-28cc3e7dc24d4208e159View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0900000000-3eb3455ff5fbfa8a3a2cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-bf788cb34c09c6af56bfView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureDermal (MSDS) ; eye contact (MSDS) ; inhalation (MSDS); oral (MSDS)
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 (19, 20). These fatty acids were also shown to induce oxidative stress in the brain (21). Experiments suggest that OA and DA impair brain mitochondrial energy homeostasis that could underlie at least in part the neuropathology of MCADD. (22)
MetabolismCapric acid (decanoic acid) is rapidly metabolized by the β-oxidative pathway, giving rise to C8- and C6-dicarboxylic acids (23). The 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 ValuesLD50: 3730 mg/kg (Oral, Rat) (MSDS) LD50: 1770 mg/kg (Dermal, Rabbit) (MSDS)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (25)
Uses/SourcesCapric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid is used in the manufacturing of esters for artificial fruit flavors and perfumes. It is also use as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. (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. (22)
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) Irritating to the skin, lung, or gastrointestinal tract, depending on the route of exposure (MSDS).
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. (22)
Concentrations
Not Available
DrugBank IDDB03600
HMDB IDHMDB0000511
FooDB IDFDB012027
Phenol Explorer IDNot Available
KNApSAcK IDC00001213
BiGG IDNot Available
BioCyc IDCPD-3617
METLIN ID336
PDB IDNot Available
Wikipedia LinkDecanoic acid
Chemspider ID2863
ChEBI ID30813
PubChem Compound ID2969
Kegg Compound IDC01571
YMDB IDYMDB00677
ECMDB IDECMDB24048
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.
2. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.
3. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
4. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.
5. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.
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28. Coyne CB, Ribeiro CM, Boucher RC, Johnson LG: Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability. J Pharmacol Exp Ther. 2003 May;305(2):440-50. Epub 2003 Feb 11.
29. Tanaka S, Saitoh O, Tabata K, Matsuse R, Kojima K, Sugi K, Nakagawa K, Kayazawa M, Teranishi T, Uchida K, Hirata I, Katsu K: Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids. J Gastroenterol Hepatol. 2001 Jul;16(7):748-54.
30. Duran M, Mitchell G, de Klerk JB, de Jager JP, Hofkamp M, Bruinvis L, Ketting D, Saudubray JM, Wadman SK: Octanoic acidemia and octanoylcarnitine excretion with dicarboxylic aciduria due to defective oxidation of medium-chain fatty acids. J Pediatr. 1985 Sep;107(3):397-404.
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34. https://www.ncbi.nlm.nih.gov/pubmed/?term=19168249
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36. https://www.ncbi.nlm.nih.gov/pubmed/?term=24284257
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