ContaminantDB: Caprylic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-09-05 17:11:58 UTC

Update Date

2026-05-14 18:08:47 UTC

Accession Number

CHEM003554

Identification

Common Name

Caprylic acid

Class

Small Molecule

Description

Caprylic 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.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Dye
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Heptanecarboxylic acid	ChEBI
8:0	ChEBI
Acide octanoique	ChEBI
Acido octanoico	ChEBI
Acidum octanocium	ChEBI
Acidum octanoicum	ChEBI
C8:0	ChEBI
CH3-[CH2]6-COOH	ChEBI
Kaprylsaeure	ChEBI
N-Caprylic acid	ChEBI
N-Octanoic acid	ChEBI
N-Octoic acid	ChEBI
N-Octylic acid	ChEBI
OCTANOIC ACID (caprylIC ACID)	ChEBI
Octansaeure	ChEBI
Octoic acid	ChEBI
Octylic acid	ChEBI
Octanoate	Kegg
1-Heptanecarboxylate	Generator
N-Caprylate	Generator
N-Octanoate	Generator
N-Octoate	Generator
N-Octylate	Generator
OCTANOate (caprylate)	Generator
Octoate	Generator
Octylate	Generator
Octanoic acid	Generator
Caprylate	Generator
Emery 657	HMDB
Kortacid 0899	HMDB
Lunac 8-95	HMDB
Lunac 8-98	HMDB
Neo-fat 8	HMDB
Neo-fat 8S	HMDB
Prifac 2901	HMDB
Caprylic acid, cadmium salt	HMDB
Caprylic acid, cesium salt	HMDB
Caprylic acid, manganese salt	HMDB
Caprylic acid, nickel(+2) salt	HMDB
Caprylic acid, zinc salt	HMDB
Caprylic acid, aluminum salt	HMDB
Caprylic acid, barium salt	HMDB
Caprylic acid, chromium(+2) salt	HMDB
Caprylic acid, lead(+2) salt	HMDB
Caprylic acid, potassium salt	HMDB
Caprylic acid, tin(+2) salt	HMDB
Sodium octanoate	HMDB
Caprylic acid, 14C-labeled	HMDB
Caprylic acid, lithium salt	HMDB
Caprylic acid, ruthenium(+3) salt	HMDB
Caprylic acid, sodium salt	HMDB
Caprylic acid, sodium salt, 11C-labeled	HMDB
Caprylic acid, tin salt	HMDB
Caprylic acid, zirconium salt	HMDB
Sodium caprylate	HMDB
Caprylic acid, ammonia salt	HMDB
Caprylic acid, calcium salt	HMDB
Caprylic acid, cobalt salt	HMDB
Caprylic acid, copper salt	HMDB
Caprylic acid, copper(+2) salt	HMDB
Caprylic acid, iridum(+3) salt	HMDB
Caprylic acid, iron(+3) salt	HMDB
Caprylic acid, lanthanum(+3) salt	HMDB
Caprylic acid, zirconium(+4) salt	HMDB
FA(8:0)	HMDB
Lithium octanoate	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Mass

144.211 g/mol

Monoisotopic Mass

144.115 g/mol

CAS Registry Number

124-07-2

IUPAC Name

octanoic acid

Traditional Name

caprylic acid

SMILES

CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)

InChI Key

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:28837 )
straight-chain saturated fatty acid (CHEBI:28837 )
Straight chain fatty acids (C06423 )
Saturated fatty acids (C06423 )
Straight chain fatty acids (LMFA01010008 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Epidermis

Pathways

Not Available

Applications

antibacterial agent

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Oily colorless liquid.

Experimental Properties

Property	Value
Melting Point	16.5°C
Boiling Point	239°C
Solubility	789 mg/L (at 30°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	2.92	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.28 m³·mol⁻¹	ChemAxon
Polarizability	17.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9000000000-74cfce03769b41313952	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uyi-0931100000-7668e36e436054042b5c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-9ecb4ccb46e89710f76a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9100000000-8854c56056d8d3405087	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-062l-9100000000-67da39159980b9078fab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0900000000-bb237630bedcee6145d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-2900000000-98284f50a271878c8481	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-5900000000-209fbbacd4996b9a770d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03kc-9000000000-74cfce03769b41313952	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e2c4dff10393086340f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-bbde8564b4e5543a636a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative	splash10-0006-0900000000-d219a0c6559a4783fd81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-e2c4dff10393086340f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-bbde8564b4e5543a636a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-0900000000-ca22ecd0b25fa371fc73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gvp-9100000000-58c00a2024ba0bae4ff4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-2505e6738cf5d5877654	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1ab4cdf8f74c93312743	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-ac7c80e50c93b8cc3af7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-d2694b5f89d8eaeb2ab1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f2b24072c91d8b0e4078	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-ad62d44e72f4dd1760ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-7900000000-9c869b84815f21dffc7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b8a648d443695914e479	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-9100000000-f5c38fdad70b324e75ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bee103956686b4840d1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-e7cbd036c8e80018c825	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f2b048da6331570976c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-cd31ca01a5fa6be86acb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-682c215be5abe1fe87ed	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion

Mechanism of Toxicity

It 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)

Metabolism

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 Values

Oral rat LD₅₀: 10080 mg/kg. Intravenous mouse LD₅₀: 600 mg/kg. Skin rabbit LD₅₀: over 5000 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Caprylic 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 Level

Not Available

Health Effects

Octanoic (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)

Symptoms

MCADD 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)

Treatment

Management 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)

Concentrations

Not Available

External Links

DrugBank ID

DB04519

HMDB ID

HMDB0000482

FooDB ID

FDB003336

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

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.

MSDS

Link

General References

1. Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.

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.

6. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.

7. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.

8. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.

9. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386