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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:41:40 UTC
NP-MRD IDNP0000313
Secondary Accession NumbersNone
Natural Product Identification
Common NameCapric acid
DescriptionCapric acid, also known as decanoic acid is a C10 saturated fatty acid. It 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 for goat). These fatty acids are light yellowish transparent oily liquids with a sweaty, unpleasant aroma that is reminiscent of goats. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric 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, caproic acid (a C6:0 Fatty acid) and caprylic acid (a C8:0 Fatty acid) account for about 15% of the fatty acids in goat milk fat (PMID 16747831 ). Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, which may occur via PPARgamma receptor agonism and the targeting of genes involved in mitochondrial biogenesis (PMIDL 24383952).
Structure
Thumb
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 Mass172.2646 Da
Monoisotopic Mass172.14633 Da
IUPAC Namedecanoic acid
Traditional Namecapric acid
CAS Registry Number334-48-5
SMILES
CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
InChI KeyGHVNFZFCNZKVNT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-10View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agave decipiensLOTUS Database
Ailuropoda melanoleucaLOTUS Database
Alpinia latilabrisLOTUS Database
Anthemis aciphyllaLOTUS Database
Anthemis aciphylla BOISS.var.discoidea BOISSPlant
Anthemis tinctoriaLOTUS Database
Arabidopsis thalianaPlant
Arnica montanaLOTUS Database
Artemisia xerophyticaLOTUS Database
Attalea colendaLOTUS Database
Attalea speciosaLOTUS Database
Bellis perennisLOTUS Database
Canarium albumLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Chlamydomonas reinhardtiiLOTUS Database
Cinnamomum triplinerveLOTUS Database
Cistus creticusPlant
Citropsis articulataLOTUS Database
Citrus aurantiifoliaLOTUS Database
Clinopodium gilliesiiLOTUS Database
Cocos nuciferaPlant
Coriandrum sativumLOTUS Database
Cuphea koehneanaPlant
Cuphea spp.Plant
Cyperus conglomeratusLOTUS Database
Daphne papyraceaLOTUS Database
Dictamnus albusLOTUS Database
Dipteryx lacuniferaLOTUS Database
Drymaria cordataPlant
Duhaldea cappaLOTUS Database
Elaeagnus angustifoliaLOTUS Database
Erigeron philadelphicusLOTUS Database
Erucaria microcarpaLOTUS Database
Eryngium foetidumLOTUS Database
Etlingera elatiorLOTUS Database
Fagopyrum esculentumLOTUS Database
Festuca rubraLOTUS Database
Geum heterocarpumLOTUS Database
Glycyrrhiza glabraLOTUS Database
Gossypium hirsutumLOTUS Database
Helichrysum stoechasLOTUS Database
Homo sapiens (Serum)Animalia
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Hypericum maculatumLOTUS Database
Hypericum perforatumLOTUS Database
Isatis tinctoriaLOTUS Database
Lepidium meyeniiLOTUS Database
Lindera neesianaLOTUS Database
Litsea glutinosaLOTUS Database
Litsea monopetalaPlant
Lonicera japonicaLOTUS Database
Lumbricus terrestrisLOTUS Database
Malva sylvestrisLOTUS Database
Mandragora autumnalisLOTUS Database
Mentha spicataLOTUS Database
Momordica charantiaLOTUS Database
Narthecium ossifragumLOTUS Database
Necrodes surinamensisLOTUS Database
Notopterygium franchetiiLOTUS Database
Nymphaea albaPlant
Oecophylla smaragdinaLOTUS Database
Origanum vulgareLOTUS Database
Pelargonium graveolensLOTUS Database
Phaseolus coccineusLOTUS Database
Pinus radiataLOTUS Database
Pinus sibiricaPlant
Plumeria rubraLOTUS Database
Portulaca oleraceaLOTUS Database
Psidium guajavaLOTUS Database
Punica granatumPlant
Pycnandra acuminataLOTUS Database
Rhodiola roseaPlant
Rhododendron sichotenseLOTUS Database
Ruellia tuberosaLOTUS Database
Salmonella entericaLOTUS Database
Salvadora oleoidesLOTUS Database
Salvia fruticosaLOTUS Database
Saussurea involucrataLOTUS Database
Saxifraga stoloniferaLOTUS Database
Saxifraga stolonifera Meerb.Plant
Scutellaria baicalensisLOTUS Database
Sebertia acuminataPlant
Senecio adenotrichiusLOTUS Database
Serenoa repensLOTUS Database
Sideritis tauricaLOTUS Database
Sinapis albaPlant
Solanum pennelliiLOTUS Database
Syagrus romanzoffianaLOTUS Database
Tanacetum macrophyllumPlant
Tilia platyphyllosLOTUS Database
Tordylium apulumLOTUS Database
Trigonella foenum-graecumLOTUS Database
Tripleurospermum maritimumLOTUS Database
Vitis viniferaLOTUS Database
Xerula pudensLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point31.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.062 mg/mLNot Available
LogP4.09Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000511
DrugBank IDDB03600
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030804
KNApSAcK IDC00001213
Chemspider ID2863
KEGG Compound IDC01571
BioCyc IDCPD-3617
BiGG IDNot Available
Wikipedia LinkDecanoic acid
METLIN ID336
PubChem Compound2969
PDB IDNot Available
ChEBI ID30813
Good Scents IDrw1007741
References
General References
  1. Farrington CJ, Chalmers AH: Gas-chromatographic estimation of urinary oxalate and its comparison with a colorimetric method. Clin Chem. 1979 Dec;25(12):1993-6. [PubMed:509698 ]
  2. Lima TM, Kanunfre CC, Pompeia C, Verlengia R, Curi R: Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis. Toxicol In Vitro. 2002 Dec;16(6):741-7. [PubMed:12423658 ]
  3. Wanten GJ, Janssen FP, Naber AH: Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. Eur J Clin Invest. 2002 Apr;32(4):285-9. [PubMed:11952815 ]
  4. Lindmark T, Kimura Y, Artursson P: Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells. J Pharmacol Exp Ther. 1998 Jan;284(1):362-9. [PubMed:9435199 ]
  5. Kaiya H, Van Der Geyten S, Kojima M, Hosoda H, Kitajima Y, Matsumoto M, Geelissen S, Darras VM, Kangawa K: Chicken ghrelin: purification, cDNA cloning, and biological activity. Endocrinology. 2002 Sep;143(9):3454-63. [PubMed:12193558 ]
  6. Eriksson T, Bjorkman S, Roth B, Fyge A, Hoglund P: Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality. 1998;10(3):223-8. [PubMed:9499573 ]
  7. Da Silva MA, Medeiros VC, Langone MA, Freire DM: Synthesis of monocaprin catalyzed by lipase. Appl Biochem Biotechnol. 2003 Spring;105 -108:757-67. [PubMed:12721413 ]
  8. Imai T, Sakai M, Ohtake H, Azuma H, Otagiri M: Absorption-enhancing effect of glycyrrhizin induced in the presence of capric acid. Int J Pharm. 2005 Apr 27;294(1-2):11-21. [PubMed:15814227 ]
  9. Leopold CS, Lippold BC: An attempt to clarify the mechanism of the penetration enhancing effects of lipophilic vehicles with differential scanning calorimetry (DSC). J Pharm Pharmacol. 1995 Apr;47(4):276-81. [PubMed:7791023 ]
  10. Saso L, Valentini G, Grippa E, Leone MG, Silvestrini B: Effect of selected substances on heat-induced aggregation of albumin, IgG and lysozyme. Res Commun Mol Pathol Pharmacol. 1998 Oct;102(1):15-28. [PubMed:9920343 ]
  11. Kaiya H, Kojima M, Hosoda H, Riley LG, Hirano T, Grau EG, Kangawa K: Identification of tilapia ghrelin and its effects on growth hormone and prolactin release in the tilapia, Oreochromis mossambicus. Comp Biochem Physiol B Biochem Mol Biol. 2003 Jul;135(3):421-9. [PubMed:12831762 ]
  12. 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. [PubMed:12606647 ]
  13. 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. [PubMed:11446882 ]
  14. 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. [PubMed:4032135 ]
  15. Wallon C, Braaf Y, Wolving M, Olaison G, Soderholm JD: Endoscopic biopsies in Ussing chambers evaluated for studies of macromolecular permeability in the human colon. Scand J Gastroenterol. 2005 May;40(5):586-95. [PubMed:16036512 ]
  16. Van Immerseel F, De Buck J, Boyen F, Bohez L, Pasmans F, Volf J, Sevcik M, Rychlik I, Haesebrouck F, Ducatelle R: Medium-chain fatty acids decrease colonization and invasion through hilA suppression shortly after infection of chickens with Salmonella enterica serovar Enteritidis. Appl Environ Microbiol. 2004 Jun;70(6):3582-7. [PubMed:15184160 ]
  17. Andersen JV, Westi EW, Jakobsen E, Urruticoechea N, Borges K, Aldana BI: Astrocyte metabolism of the medium-chain fatty acids octanoic acid and decanoic acid promotes GABA synthesis in neurons via elevated glutamine supply. Mol Brain. 2021 Sep 3;14(1):132. doi: 10.1186/s13041-021-00842-2. [PubMed:34479615 ]