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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/13 20:49:45」(JST)

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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.^[5] 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

^ ^a ^b ^c ^d ^e Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
^ at 2.06–2.63 K
^ at −191 °C
^ ^a ^b Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685.
^ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
^ B. Martena, M. Pfeuffer, J. Schrezenmeir (2006). "Medium-chain triglycerides". International Dairy Journal 16 (11): 1374–1382. doi:10.1016/j.idairyj.2006.06.015.
^ Takeuchi, H; Sekine, S; Kojima, K; Aoyama, T (2008). "The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation". Asia Pacific journal of clinical nutrition. 17 Suppl 1: 320–3. PMID 18296368.
^ St-Onge, MP; Jones, PJ (2002). "Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity". The Journal of nutrition 132 (3): 329–32. PMID 11880549.
^ Papamandjaris, AA; MacDougall, DE; Jones, PJ (1998). "Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications". Life Sciences 62 (14): 1203–15. doi:10.1016/S0024-3205(97)01143-0. PMID 9570335.
^ Clegg, M. E. (2010). "Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance". International Journal of Food Sciences and Nutrition 61 (7): 653–679. doi:10.3109/09637481003702114. PMID 20367215.
^ 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.
^ Omura, Y; O'Young, B; Jones, M; Pallos, A; Duvvi, H; Shimotsuura, Y (2011). "Caprylic acid in the effective treatment of intractable medical problems of frequent urination, incontinence, chronic upper respiratory infection, root canalled tooth infection, ALS, etc., caused by asbestos & mixed infections of Candida albicans, Helicobacter pylori & cytomegalovirus with or without other microorganisms & mercury". Acupuncture & electro-therapeutics research 36 (1–2): 19–64. PMID 21830350.

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English Journal

Engineering Yarrowia lipolytica for production of medium-chain fatty acids.

Rutter CD1, Zhang S, Rao CV.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2015 Sep;99(17):7359-68. doi: 10.1007/s00253-015-6764-1. Epub 2015 Jul 1.
Lipids are naturally derived products that offer an attractive, renewable alternative to petroleum-based hydrocarbons. While naturally produced long-chain fatty acids can replace some petroleum analogs, medium-chain fatty acid would more closely match the desired physical and chemical properties of
PMID 26129951

Octanoic acid promotes branched-chain amino acid catabolisms via the inhibition of hepatic branched-chain alpha-keto acid dehydrogenase kinase in rats.

Kadota Y1, Toyoda T1, Hayashi-Kato M1, Kitaura Y1, Shimomura Y2.
Metabolism: clinical and experimental.Metabolism.2015 Sep;64(9):1157-64. doi: 10.1016/j.metabol.2015.05.014. Epub 2015 Jun 3.
OBJECTIVE: It has been reported that administration of octanoic acid, one of medium-chain fatty acids (MCFAs), promoted leucine oxidation in vitro and in vivo, but it remained unclear how octanoic acid stimulated leucine oxidation. Therefore, the aim of this study was to elucidate the mechanism that
PMID 26104959

Caprylic acid-induced impurity precipitation from protein A capture column elution pool to enable a two chromatography step process for monoclonal antibody purification.

Zheng J1, Wang L1, Twarowska B1, Laino S1, Sparks C1, Smith T1, Russell R1, Wang M1.
Biotechnology progress.Biotechnol Prog.2015 Aug 17. doi: 10.1002/btpr.2154. [Epub ahead of print]
This paper presents the use of caprylic acid to precipitate impurities from the protein A capture column elution pool for the purification of monoclonal antibodies (mAbs) with the objective of developing a two chromatography step antibody purification process. A caprylic acid-induced impurity precip
PMID 26280674

Japanese Journal

One-step preparation of S-nitrosated human serum albumin with high biological activities

Yu Ishima,Shuichi Hiroyama,Ulrich Kragh-Hansen,Toru Maruyama,Tomohiro Sawa,Takaaki Akaike,Toshiya Kai,Masaki Otagiri,イシマユウ,ヒロヤマシュウイチ,マルヤマトオル,サワトモヒロ,アカイケタカアキ,カイトシヤ,オタギリマサキ,異島優,廣山秀一,丸山徹,澤智裕,赤池孝章,甲斐俊哉,小田切優樹
Nitric Oxide 23(2), 121-127, 2010-09-15
… We found that binding of caprylic acid (CA) and N-acetyl-L-tryptophan (N-AcTrp) to defatted mercaptalbumin increased S-nitrosation by S-nitrosoglutathione (GS-NO) by making Cys-34 of HSA more accessible and by protecting it against oxidation, respectively. …
NAID 120002971552

Decomposition Kinetics of 6-O-Monoacyl Ascorbate in Air

WATANABE Yoshiyuki,SAWAHARA Yuki,ASAI Shinichi,ADACHI Shuji
Food science and technology research 14(2), 139-143, 2008-03-01
… 6-O-Monoacyl ascorbates were synthesized by the condensation of L-ascorbic acid with caprylic, capric, lauric, myristic or palmitic acid using immobilized lipase in acetone. …
NAID 10021184897

Related Pictures

★リンクテーブル★

リンク元	「caprylate」「カプリル酸」「octanoate」「octanoic acid」「オクタン酸」

「caprylate」

Caprylic acid
Names
	IUPAC name octanoic acid
	Other names C8:0 (Lipid numbers)
Identifiers
CAS Registry Number	124-07-2
ChEBI	CHEBI:28837
ChEMBL	ChEMBL324846
ChemSpider	370
DrugBank	DB04519
EC number	204-677-5
	InChI InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) ; Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N ; InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10); Key: WWZKQHOCKIZLMA-UHFFFAOYAH ;
IUPHAR/BPS	4585
Jmol-3D images	Image
KEGG	D05220
PubChem	379
	SMILES CCCCCCCC(=O)O ;
UNII	OBL58JN025
Properties
Chemical formula	C8H16O2
Molar mass	144.21 g/mol
Appearance	Oily colorless liquid
Odor	faint, fruity-acid; irritating
Density	0.910 g/cm3
Melting point	16.7 °C (62.1 °F; 289.8 K)
Boiling point	239.7 °C (463.5 °F; 512.8 K)
Solubility in water	0.068 g/100 mL
Solubility	soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile
log P	3.05
Vapor pressure	0.25 Pa
Acidity (pKa)	4.89; 1.055; 1.53
Refractive index (nD)	1.4285
Thermochemistry
Specific; heat capacity (C)	297.9 J/K mol
Std enthalpy of; formation (ΔfHo298)	-636 kJ/mol
Hazards
NFPA 704	0 3 1 COR
Flash point	130 °C (266 °F; 403 K)
Autoignition; temperature	440 °C (824 °F; 713 K)
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	10.08 g/kg (orally in rats)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references