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Caprylic acid

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Caprylic acid

Dangerous for the Environment (Nature) N|
Caprylic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
octanoic acid
Other names
C8:0 (Lipid numbers)
Identifiers
 YesY
ChEBI  YesY
ChEMBL  YesY
ChemSpider  YesY
DrugBank  YesY
EC number 204-677-5
Jmol-3D images Image
KEGG  YesY
PubChem
UNII  YesY
Properties
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} }}}}
Documentation

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]

1.055[4]
1.53[5]

1.4285
Thermochemistry
297.9 J/K mol
Hazards
NFPA 704
0
3
1
COR
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.

Uses

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]

References

  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. ^
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