World Library  
Flag as Inappropriate
Email this Article

Caprylic acid

Article Id: WHEBN0003127774
Reproduction Date:

Title: Caprylic acid  
Author: World Heritage Encyclopedia
Language: English
Subject: Ester, Carboxylic acid, Undecylic acid, Outline of nutrition, Asimina triloba
Publisher: World Heritage Encyclopedia

Caprylic acid

Dangerous for the Environment (Nature) N|
Caprylic acid
Skeletal formula
Ball-and-stick model
IUPAC name
octanoic acid
Other names
C8:0 (Lipid numbers)
ChemSpider  YesY
DrugBank  YesY
EC number 204-677-5
Jmol-3D images Image
small=yes}}} }}} 0}}} 1=C|C} }}} 1=H|H} }}} 1=Ac|Ac} }}} 1=Ag|Ag} }}} 1=Al|Al} }}} 1=Am|Am} }}} 1=Ar|Ar} }}} 1=As|As} }}} 1=At|At} }}} 1=Au|Au} }}} 1=B|B} }}} 1=Ba|Ba} }}} 1=Be|Be} }}} 1=Bh|Bh} }}} 1=Bi|Bi} }}} 1=Bk|Bk} }}} 1=Br|Br} }}} 1=Ca|Ca} }}} 1=Cd|Cd} }}} 1=Ce|Ce} }}} 1=Cf|Cf} }}} 1=Cn|Cn} }}} 1=Cl|Cl} }}} 1=Cm|Cm} }}} 1=Co|Co} }}} 1=Cr|Cr} }}} 1=Cs|Cs} }}} 1=Cu|Cu} }}} 1=Db|Db} }}} 1=Ds|Ds} }}} 1=Dy|Dy} }}} 1=Er|Er} }}} 1=Es|Es} }}} 1=Eu|Eu} }}} 1=F|F} }}} 1=Fe|Fe} }}} 1=Fl|Fl} }}} 1=Fm|Fm} }}} 1=Fr|Fr} }}} 1=Ga|Ga} }}} 1=Gd|Gd} }}} 1=Ge|Ge} }}} 1=He|He} }}}}

Appearance Oily colorless liquid
Odor faint, fruity-acid; irritating
Density 0.910 g/cm3[1]
Melting point 16.7 °C (62.1 °F; 289.8 K)[2]
Boiling point 239.7 °C (463.5 °F; 512.8 K)[1]
0.068 g/100 mL[1]
Solubility soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile
log P 3.05
Vapor pressure 0.25 Pa
Acidity (pKa) 4.89[3]


297.9 J/K mol
NFPA 704
Flash point 130 °C (266 °F; 403 K)
440 °C (824 °F; 713 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
10.08 g/kg (orally in rats)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY  (: YesY/N?)

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. Its compounds are found naturally in the milk of various mammals, and as a minor constituent of coconut oil and palm kernel oil.[2] It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.[1]

Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15% in goat milk fat.


Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes.

It has been observed that Malonyl-CoA inhibits palmitic acid oxidation in isolated mitochondria, but that it has little or no effect on the oxidation of octanoic acid (C8, Saturated). This observation can be explained by AMP functions serving as an energy sensor and regulator of metabolism. When ATP production does not keep up with needs, a higher portion of a cell's adenine nucleotide pool is in the form of AMP. AMP promotes catabolic pathways that lead to synthesis of ATP, while inhibiting energy-utilizing synthetic pathways. For example, AMP regulates fatty acid synthesis and catabolism by controlling availability of malonyl-CoA.

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.[6]

For ghrelin to have a hunger-stimulating action on a hypothalamus, caprylic acid must be linked to a serine residue at the 3-position of ghrelin. To cause hunger, it must acylate an -OH group. Other fatty acids in the same position have similar effects on hunger.

The acid chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.

Dietary uses

Caprylic acid is taken as a dietary supplement.

Some studies have shown that MCTs can help in the process of excess calorie burning, and thus weight loss.[7][8][9][10] MCTs are also seen as promoting fat oxidation and reduced food intake.[11] There has also been interest in MCTs from endurance athletes and the bodybuilding community.[12]

It is believed to suppress fungal infections within the gut, notably candida albicans infection.[13]


  1. ^ a b c d e
  2. ^ a b
  3. ^
  4. ^ at 2.06–2.63 K
  5. ^ at −191 °C
  6. ^ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
  7. ^
  8. ^
  9. ^
  10. ^
  11. ^
  12. ^ Talbott, Shawn M. and Kerry Hughes. (2006). The Health Professional's Guide to Dietary Supplements. Lippincott Williams & Wilkins. pp. 60–63. ISBN 978-0-7817-4672-4.
  13. ^
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.