関: capric acid、decanoate

WordNet

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"

PrepTutorEJDIC

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）』「2015/07/02 18:00:28」(JST)

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For the term capric as it related to music see Capriccio (music)

Decanoic acid (capric acid) is a saturated fatty acid. Its formula is CH₃(CH₂)₈COOH. Salts and esters of decanoic acid are called decanoates or "caprates". The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.^[9]

Occurrence

Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.^[10] It is found in the milk of various mammals and to a lesser extent in other animal fats.^[6]

Two other acids are named after goats: caproic (a C6 fatty acid) and caprylic (a C8 fatty acid). Along with decanoic acid, these total 15% in goat milk fat.

Production

Decanoic acid can be prepared from oxidation of primary alcohol decanol by using chromium trioxide (CrO₃) oxidant under acidic conditions.^[11]

Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide will give sodium decanoate. This salt (CH₃(CH₂)₈COO⁻Na⁺) is a component of some types of soap.

Use

Decanoic acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.^[8]

Pharmaceuticals

Decanoate ester prodrugs of various pharmaceuticals are available. Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for fatty tissue. Since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using its decanoate form. Some examples of drugs available as a decanoate ester include nandrolone, fluphenazine, bromperidol, and haloperidol.

References

^ ^a ^b ^c ^d n-Decanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-15)
^ ^a ^b ^c ^d ^e CID 2969 from PubChem
^ ^a ^b ^c ^d ^e ^f Sigma-Aldrich Co., Decanoic acid. Retrieved on 2014-06-15.
^ ^a ^b ^c Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering Data on Mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.
^ ^a ^b ^c ^d ^e ^f Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
^ ^a ^b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.
^ ^a ^b ^c Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-15.
^ ^a ^b ^c "CAPRIC ACID". http://www.chemicalland21.com. AroKor Holdings Inc. Retrieved 2014-06-15.
^ "capri-, capr- +". Retrieved 2012-09-28.
^ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
^ John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624

UpToDate Contents

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1. 尿酸のバランス uric acid balance
2. 出産時の臍帯血酸塩基分析 umbilical cord blood acid base analysis at delivery
3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
4. ポルフィリン症：概要 porphyrias an overview
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

Decanoic acid-modified glycol chitosan hydrogels containing tightly adsorbed palmityl-acylated exendin-4 as a long-acting sustained-release anti-diabetic system.

Lee C1, Choi JS1, Kim I1, Byeon HJ1, Kim TH1, Oh KT2, Lee ES3, Lee KC1, Youn YS4.Author information 1School of Pharmacy, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon 440-746, Republic of Korea.2College of Pharmacy, Chung-Ang University, 221 Heukseok dong, Dongjak-gu, Seoul 155-756, Republic of Korea.3Division of Biotechnology, The Catholic University of Korea, 43-1 Yeokgok 2-dong, Wonmi-gu, Bucheon-si, Gyeonggi-do 420-743, Republic of Korea.4School of Pharmacy, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon 440-746, Republic of Korea. Electronic address: ysyoun@skku.edu.AbstractDecanoic acid-modified glycol chitosan (DA-GC) hydrogels containing tightly adsorbed palmitic acid-modified exendin-4 (Ex4-C16) were prepared, and their pharmaceutical abilities as a long-acting sustained-release exendin-4 system for the treatment of diabetes were evaluated. Glycol chitosan (GC) was conjugated with N-hydroxysuccinimide-activated decanoic acid (DA) in anhydrous 0.4% dimethylaminopyridine/dimethylsulfoxide at different feed ratios. DA-GC hydrogels formed by physical self-assembly during dialysis vs. deionized water, and their inner network structures, swelling or gel-forming abilities and release properties were examined. The hypoglycemia caused by Ex4-C16-loaded DA-GC hydrogels was evaluated by subcutaneous administration in type 2 diabetic db/db mice. The results obtained showed that GC prepared at a DA:GC feed ratio of 1:100 had optimal properties with respect to hydrogel swelling, stiffness and Ex4-C16 incorporation, whereas DA-GC hydrogels prepared at a feed ratio of greater than 1:100 formed gels that were too stiff. The in vitro and in vivo release of Ex4-C16 from DA-GC hydrogels was dramatically delayed compared with native Ex4 probably due to strong hydrophobic interactions. In particular, Ex4-C16 in DA-GC hydrogels was found to be present around the injection site up to 10days after subcutaneous administration, whereas Ex4 in DA-GC hydrogels was cleared from injection sites in ∼2days in ICR mice. Finally, the hypoglycemia induced by Ex4-C16 DA-GC hydrogels was maintained for >7days. Our findings demonstrate that Ex4-C16 DA-GC hydrogels offer a potential delivery system for the long-term treatment of type 2 diabetes.
Acta biomaterialia.Acta Biomater.2014 Feb;10(2):812-20. doi: 10.1016/j.actbio.2013.10.009. Epub 2013 Oct 17.
Decanoic acid-modified glycol chitosan (DA-GC) hydrogels containing tightly adsorbed palmitic acid-modified exendin-4 (Ex4-C16) were prepared, and their pharmaceutical abilities as a long-acting sustained-release exendin-4 system for the treatment of diabetes were evaluated. Glycol chitosan (GC) was
PMID 24140611

Production of poly-3-(hydroxybutyrate-co-hydroxyvalerate) by Haloferax mediterranei using rice-based ethanol stillage with simultaneous recovery and re-use of medium salts.

Bhattacharyya A, Saha J, Haldar S, Bhowmic A, Mukhopadhyay UK, Mukherjee J.Author information School of Environmental Studies, Jadavpur University, Kolkata, 700 032, India.AbstractHaloferax mediterranei holds promise for competitive industrial-scale production of polyhydroxyalkanoate (PHA) because cheap carbon sources can be used thus lowering production costs. Although high salt concentration in production medium permits a non-sterile, low-cost process, salt disposal after process completion is a problem as current environmental standards do not allow total dissolved solids (TDS) above 2000 mg/l in discharge water. As the first objective of this work, the waste product of rice-based ethanol industry, stillage, was used for the production of PHA by H. mediterranei in shake flasks. Utilization of raw stillage led to 71 ± 2 % (of dry cell weight) PHA accumulation and 16.42 ± 0.02 g/l PHA production. The product yield coefficient was 0.35 while 0.17 g/l h volumetric productivity was attained. Simultaneous reduction of BOD5 and COD values of stillage by 83 % was accomplished. The PHA was isolated by osmotic lysis of cells, purification by sodium dodecyl sulfate and organic solvents. The biopolymer was identified as poly-3-(hydroxybutyrate-co-15.4 mol%-hydroxyvalerate) (PHBV). This first report on utilization of rice-based ethanol stillage for PHBV production by H. mediterranei is currently the most cost effective. As the second objective, directional properties of decanoic acid together with temperature dependence of water solubility in decanoic acid were applied for two-stage desalination of the spent stillage medium. We report for the first time, recovery and re-use of 96 % of the medium salts for PHA production thus removing the major bottleneck in the potential application of H. mediterranei for industrial production of PHBV. Final discharge water had TDS content of 670 mg/l.
Extremophiles : life under extreme conditions.Extremophiles.2014 Jan 19. [Epub ahead of print]
Haloferax mediterranei holds promise for competitive industrial-scale production of polyhydroxyalkanoate (PHA) because cheap carbon sources can be used thus lowering production costs. Although high salt concentration in production medium permits a non-sterile, low-cost process, salt disposal after p
PMID 24442255

The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells.

Hughes SD, Kanabus M, Anderson G, Hargreaves IP, Rutherford T, O'Donnell M, Cross JH, Rahman S, Eaton S, Heales SJ.Author information Clinical and Molecular Genetics Unit, UCL Institute of Child Health, UK; Chemical Pathology, Great Ormond Street Hospital for Children NHS Foundation Trust, London, UK.AbstractThe Ketogenic diet (KD) is an effective treatment with regards to treating pharmaco-resistant epilepsy. However, there are difficulties around compliance and tolerability. Consequently, there is a need for refined/simpler formulations that could replicate the efficacy of the KD. One of the proposed hypotheses is that the KD increases cellular mitochondrial content which results in elevation of the seizure threshold. Here, we have focussed on the medium-chain triglyceride (MCT) form of the diet and the observation that plasma octanoic acid (C8) and decanoic acid (C10) levels are elevated in patients on the MCT KD. Using a neuronal cell line (SH-SY5Y), we demonstrated that 250uM C10, but not C8, caused, over a 6-day period, a marked increase in the mitochondrial enzyme, citrate synthase along with complex I activity and catalase activity. Increased mitochondrial number was also indicated by electron microscopy. C10 is a reported PPARγ agonist and the use of a PPARγ antagonist was shown to prevent the C10-mediated increase in mitochondrial content and catalase. C10 may mimic the mitochondrial proliferation associated with the KD and raises the possibility that formulations based on this fatty acid could replace a more complex diet. This article is protected by copyright. All rights reserved.
Journal of neurochemistry.J Neurochem.2014 Jan 3. doi: 10.1111/jnc.12646. [Epub ahead of print]
The Ketogenic diet (KD) is an effective treatment with regards to treating pharmaco-resistant epilepsy. However, there are difficulties around compliance and tolerability. Consequently, there is a need for refined/simpler formulations that could replicate the efficacy of the KD. One of the proposed
PMID 24383952

Japanese Journal

Investigation of Koku Impact Compounds in Sweet Cream on the Basis of Sensory Evaluation and Separation Techniques

KOBAYASHI Noriaki,NISHIMURA Osamu
Food science and technology research 17(3), 233-240, 2011-05-01
… fractions selected by sensory evaluation were analyzed by gas chromatography-mass spectroscopy, and 7 long-chain fatty acids (decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, and linoleic acid), 3 long-chain aliphatic delta-lactones (5-dodecanolide, 5-tetradecanolide, and 5-hexadecanolide), and cholesterol were …
NAID 10028259633

2P-1111 n-Decanoic acidを水酸化して3-Hydroxydecan-oic acidを生産する細菌の探索(3a発酵生理学,発酵工学,一般講演,代謝生理学・発酵生産,伝統の技と先端科学技術の融合)

冨永祐希,斉藤駿,本田康博,倉田淳志,岸本憲明
日本生物工学会大会講演要旨集平成22年度, 36, 2010-09-25
NAID 110008084478

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★リンクテーブル★

リンク元	「decanoate」「デカン酸」「capric acid」
拡張検索	「octadecanoic acid」「hexadecanoic acid」「beta-methyliodophenyl pentadecanoic acid」

「decanoate」

Decanoic acid
Names
	IUPAC name Decanoic acid
	Other names Capric acid, n-Capric acid, n-Decanoic acid, Decylic acid, n-Decylic acid, C10:0 (Lipid numbers)
Identifiers
CAS Registry Number	334-48-5 ; 1002-62-6 (sodium salt)
ChEBI	CHEBI:30813
ChEMBL	ChEMBL107498
ChemSpider	2863
DrugBank	DB03600
EC number	206-376-4
	InChI InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) ; Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N ; InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12); Key: GHVNFZFCNZKVNT-UHFFFAOYAC ;
IUPHAR/BPS	5532
Jmol-3D images	Image
KEGG	C01571
PubChem	2969
RTECS number	HD9100000
	SMILES O=C(O)CCCCCCCCC ;
UNII	4G9EDB6V73
Properties
Chemical formula	C10H20O2
Molar mass	172.27 g·mol−1
Appearance	White crystals
Odor	Strong rancid and unpleasant
Density	0.893 g/cm3 (25 °C); 0.8884 g/cm3 (35.05 °C); 0.8773 g/cm3 (50.17 °C)
Melting point	31.6 °C (88.9 °F; 304.8 K)
Boiling point	268.7 °C (515.7 °F; 541.8 K)
Solubility in water	0.015 g/100 mL (20 °C)
Solubility	Soluble in alcohol, ether, CHCl3, C6H6, CS2, acetone
log P	4.09
Vapor pressure	4.88·10−5 kPa (25 °C); 0.1 kPa (108 °C); 2.03 kPa (160 °C)
Acidity (pKa)	4.9
Thermal conductivity	0.372 W/m·K (solid); 0.141 W/m·K (liquid)
Refractive index (nD)	1.4288 (40 °C)
Viscosity	4.327 cP (50 °C); 2.88 cP (70 °C)
Structure
Crystal structure	Monoclinic (−3.15 °C)
Space group	P21/c
Lattice constant	a = 23.1 Å, b = 4.973 Å, c = 9.716 Å α = 90°, β = 91.28°, γ = 90°
Thermochemistry
Specific; heat capacity (C)	475.59 J/mol·K
Std enthalpy of; formation (ΔfHo298)	−713.7 kJ/mol
Std enthalpy of; combustion (ΔcHo298)	6079.3 kJ/mol
Hazards
Main hazards	Medium toxicity
Safety data sheet	External MSDS
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
EU classification	Xi
R-phrases	R36/37/38
S-phrases	S24/25, S26, S36/37/39
Ingestion hazard	May be toxic
Inhalation hazard	May cause irritation
Skin hazard	May be toxic on contact
NFPA 704	1 2 0
Flash point	110 °C (230 °F; 383 K)
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	10 g/kg (rats, oral)
Related compounds
Related fatty acids	Caprylic acid; Lauric acid
Related compounds	Decanol; Decanal
	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

　　[★]

デカン酸、(化合物)カン酸エステル

関: capric acid、decanoic acid

「デカン酸」

　　[★]

英: decanoic acid、decanoate
関: カプリン酸、デカン酸エステル

「capric acid」

　　[★]

カプリン酸

関: caprate、decanoate、decanoic acid

「octadecanoic acid」

　　[★]

オクタデカン酸

関: aluminum monostearate、calcium stearate、magnesium stearate、stearate、stearic acid

「hexadecanoic acid」

　　[★]

ヘキサデカン酸

関: palmitate、palmitic acid

「beta-methyliodophenyl pentadecanoic acid」

　　[★] β-メチルヨードフェニルペンタデカン酸

[nist-1] -Decanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-15)

[pubchem-2] CID 2969 from PubChem

[sigma-3] ^ ^a ^b ^c ^d ^e ^f Sigma-Aldrich Co., Decanoic acid. Retrieved on 2014-06-15.

[edm-4] Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering Data on Mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.

[crc-5] ^ ^a ^b ^c ^d ^e ^f Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

[lexicon-6] "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.

[adb-7] Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-15.

[cheml-8] "CAPRIC ACID". http://www.chemicalland21.com. AroKor Holdings Inc. Retrieved 2014-06-15.

[9] "capri-, capr- +". Retrieved 2012-09-28.

[Ullmann-10] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2

[11] John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624

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decanoic acid