デカン酸、(化合物)カン酸エステル

関: capric acid、decanoic acid

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/06 22:58:33」(JST)

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

Decanoic acid, or 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 arises from the Latin "capric" which pertains to goats due to their olfactory similarities.^[9]

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

Manufacturing of esters for artificial fruit flavors and perfumes. Also 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 salts and esters of various drugs 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 or salt include nandrolone, fluphenazine, bromperidol, haloperidol and vanoxerine.

Role for earliest life

A study published in 2013 outlines how decanoic acid may have primed and protected the earliest life on Earth. The scientists discovered that the four bases in RNA bound more readily to the decanoic acid than did the other seven bases tested. Furthermore, the same bases of RNA that preferentially stuck to the fatty acid also protected bags of decanoic acid from disruptive effects of salty seawater.^[12]

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". 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
^ Nucleobases bind to and stabilize aggregates of a prebiotic amphiphile, providing a viable mechanism for the emergence of protocells

UpToDate Contents

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5. 周術期の投薬マネージメント perioperative medication management

English Journal

Effect of curing salts and probiotic cultures on the evolution of flavor compounds in dry-fermented sausages during ripening.

Sidira M1, Kandylis P2, Kanellaki M2, Kourkoutas Y3.
Food chemistry.Food Chem.2016 Jun 15;201:334-8. doi: 10.1016/j.foodchem.2016.01.084. Epub 2016 Jan 21.
The effect of the concentration of curing salts, the nature of the probiotic culture (free or immobilized Lactobacillus casei ATCC 393 on wheat grains) and the ripening time on the generation of volatile compounds in probiotic dry-fermented sausages was investigated. Samples were collected after 1,
PMID 26868585

Serca2a and Na(+)/Ca(2+) exchanger are involved in left ventricular function following cardiac remodelling of female rats treated with anabolic androgenic steroid.

Nascimento AM1, Lima EM1, Brasil GA1, Caliman IF1, Silva JF2, Lemos VS2, Andrade TU3, Bissoli NS4.
Toxicology and applied pharmacology.Toxicol Appl Pharmacol.2016 Jun 15;301:22-30. doi: 10.1016/j.taap.2016.04.001. Epub 2016 Apr 10.
Anabolic-androgenic steroids are misused, including by women, but little is known about the cardiovascular effects of these drugs on women.AIM: To evaluated the effects of nandrolone decanoate (ND) and resistive physical exercise on cardiac contractility in young female rats.MAIN METHODS: Female Wis
PMID 27074353

Impact of flavouring substances on the aggregation behaviour of dissolved barley β-glucans in a model beer.

Kupetz M1, Sacher B2, Becker T1.
Carbohydrate polymers.Carbohydr Polym.2016 Jun 5;143:204-11. doi: 10.1016/j.carbpol.2016.01.070. Epub 2016 Feb 2.
Structural polymers such as cereal β-glucan may cause various processing problems in beverage industry depending on concentration, molar size distribution and agglomeration behaviour. In this context, influences of the beer volatiles dodecanoic acid, octyl butanoate, ethyl decanoate and decyl aceta
PMID 27083361

Japanese Journal

バイオディーゼルサロゲートの着火特性に関する反応論的解析(第3報)

平村義浩,大村慎太郎,桑原一成 [他]
自動車技術会論文集 43(2), 431-436, 2012-03
NAID 40019254532

Investigation of Transport Mechanism of Exendin-4 across Madin Darby Canine Kidney Cell Monolayers

Wang Mengshu,Sun Bingxue,Feng Jiao,Zhang Haihong,Liu Bin,Li Chun,Chen Yan,Zhang Yong,Kong Wei
Biological and Pharmaceutical Bulletin 35(5), 745-752, 2012
… Moreover, the apparent permeability coefficient (Papp) values of exendin-4 were determined in the presence of chitosan, sodium decanoate and ethylenediaminetetraacetic acid (EDTA) to further confirm the relative transport mechanism and to evaluate their potential utility in future formulation design. … And the order of enhancement was to the effect of chitosan>EDTA>sodium decanoate, and the order of safety was sodium decanoate≈chitosan>EDTA. …
NAID 130001872234

Lipase-catalyzed synthesis of hydrophobically modified dextrans : Activity and regioselectivity of lipase from Candida rugosa(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)

Kaewprapan Kultida,Wongkongkatep Jirarut,Panbangred Watanalai,Phinyocheep Pranee,Marie Emmanuelle,Durand Alain,Inprakhon Pranee
Journal of bioscience and bioengineering 112(2), 124-129, 2011-08
… Vinyl decanoate-modified dextran macromolecules (DexT40-VD) were synthesized in dimethyl sulfoxide at 50℃ using lipase AY from Candida rugosa for catalyzing transesterification between polysaccharide and vinyl fatty esters. …
NAID 110008711112

Related Pictures

★リンクテーブル★

リンク元	「デカン酸」「capric acid」「デカン酸エステル」「decanoic acid」
拡張検索	「nandrolone decanoate」「bromperidol decanoate」

「デカン酸」

Decanoic acid
	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 number	334-48-5 , 1002-62-6 (sodium salt)
PubChem	2969
ChemSpider	2863
UNII	4G9EDB6V73
EC number	206-376-4
DrugBank	DB03600
KEGG	C01571
ChEBI	CHEBI:30813
ChEMBL	CHEMBL107498
RTECS number	HD9100000
Jmol-3D images	Image 1
	SMILES O=C(O)CCCCCCCCC ;
	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 ;
Properties
Molecular formula	C10H20O2
Molar mass	172.26 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
Lattice constant	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
MSDS	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
Main hazards	Medium toxicity
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)
LD50	10 g/kg (rats, oral)
Related compounds
Related fatty acids	Caprylic acid; Lauric acid
Related compounds	Decanol; Decanal
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

　　[★]

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

「デカン酸エステル」

　　[★]

英: decanoate
関: カプリン酸、デカン酸

「decanoic acid」

　　[★]

デカン酸

関: capric acid、decanoate

「nandrolone decanoate」

　　[★]

デカン酸ナンドロロン

関: nandrolone、nandrolone cyclohexylpropionate、nandrolone furylpropionate、nandrolone phenylpropionate

「bromperidol decanoate」

　　[★]

デカン酸ブロムペリドール

関: bromperidol

[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". 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

[12] Nucleobases bind to and stabilize aggregates of a prebiotic amphiphile, providing a viable mechanism for the emergence of protocells

匿名

検索

案内

案内

decanoate