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"

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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）』「2012/11/21 01:53:42」(JST)

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Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common fatty acid found in animals, plants and microorganisms.^[4] Its molecular formula is CH₃(CH₂)₁₄CO₂H. As its name indicates, it is a major component of the oil from palm trees (palm oil, palm kernel oil, and coconut oil), but can also be found in meats, cheeses, butter, and dairy products. Palmitate is a term for the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at basic pH.

Palmitic acid has been shown (in rats fed on a 20% fat (palmitic acid), 80% carbohydrate diet) to alter aspects of the central nervous system responsible for the secretion of insulin, and to suppress the body's natural appetite-suppressing signals from leptin and insulin—the key hormones involved in weight regulation.^[5]

Aluminum salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm (aluminum naphthenate and aluminum palmitate). The word "napalm" is derived from the words naphthenic acid and palmitic acid.

Occurrence and production

Palmitic acid mainly occurs as its ester in triglycerides (fats), especially palm oil but also tallow. The cetyl ester of palmitic acid (cetyl palmitate) occurs in spermaceti. It was discovered by Edmond Frémy in 1840, in saponified palm oil.^[6] Butter, cheese, milk and meat also contain this fatty acid.

Palmitic acid is prepared by treating fats and oils with water at a high pressure and temperature (above 200 °C), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled.^[7]

Biochemistry

Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and the precursor to longer fatty acids. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC), which is responsible for converting acetyl-CoA to malonyl-CoA, which in turn is used to add to the growing acyl chain, thus preventing further palmitate generation.^[8] In biology, some proteins are modified by the addition of a palmitoyl group in a process known as palmitoylation. Palmitoylation is important for membrane localisation of many proteins.

Applications

Palmitic acid is mainly used to produce soaps, cosmetics, and release agents. These applications utilize sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from the coconut palm nut, is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups. This procedure affords glycerol and sodium palmitate.

Because it is inexpensive and adds texture to processed foods (convenience food), palmitic acid and its sodium salt find wide use including foodstuffs. Sodium palmitate is permitted as a natural additive in organic products.^[9]

Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics.

Recently, a long-acting antipsychotic medication, paliperidone palmitate (marketed as INVEGA Sustenna), used in the treatment of schizophrenia, has been synthesized using the oily palmitate ester as a long-acting release carrier medium when injected intramuscularly. The underlying method of drug delivery is similar to that used with decanoic acid to deliver long-acting depot medication, in particular, neuroleptics such as haloperidol decanoate.

Dietary effect

According to the World Health Organization, evidence is "convincing" that consumption of palmitic acid increases risk of developing cardiovascular diseases, placing it in the same evidence category as trans fatty acids.^[10] Retinyl palmitate is an antioxidant and a source of vitamin A added to low fat milk to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, to make vitamin A stable in milk.

References

^ Merck Index, 12th Edition, 7128.
^ 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. http://iupac.org/publications/pac/73/4/0685/.
^ Palmitic acid at Inchem.org
^ Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN 0849396883 | ISBN 978-0849396885
^ Palmitic acid mediates hypothalamic insulin resistance by altering PKC-θ subcellular localization in rodents, Journal of Clinical Investigation
^ E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757.
^ 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
^ Fatty acid biosynthesis - Reference pathway
^ US Soil Association standard 50.5.3
^ Diet, Nutrition and the Prevention of Chronic Diseases, WHO Technical Report Series 916, Report of a Joint WHO/FAO Expert Consultation, World Health Organization, Geneva, 2003, p. 88 (Table 10)

UpToDate Contents

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3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
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English Journal

Optimization of microwave-assisted extraction of cottonseed oil and evaluation of its oxidative stability and physicochemical properties.

Taghvaei M1, Jafari SM2, Assadpoor E3, Nowrouzieh S4, Alishah O4.
Food chemistry.Food Chem.2014 Oct 1;160:90-7. doi: 10.1016/j.foodchem.2014.03.064. Epub 2014 Mar 21.
Microwave assisted extraction (MAE) is a novel method, which can reduce the extraction time and solvent consumption. This study aimed to evaluate the influence of MAE on oxidative stability and physicochemical properties of cottonseed oil. We found that the optimum extraction conditions were: irradi
PMID 24799213

Nutritional and lipid profiles in marine fish species from Brazil.

Fernandes CE1, Vasconcelos MA2, de Almeida Ribeiro M3, Sarubbo LA4, Andrade SA5, Filho AB1.
Food chemistry.Food Chem.2014 Oct 1;160:67-71. doi: 10.1016/j.foodchem.2014.03.055. Epub 2014 Mar 20.
Centesimal composition and lipid profiles were evaluated in muscle tissue of four species of Brazilian fish using the Kjeldahl and Bligh & Dyer gravimetric methods and gas chromatography, respectively. The moisture, protein, total lipid, and ash values (g/100g) ranged from 71.13 to 78.39; 18.10
PMID 24799210

Japanese Journal

Ice core profiles of saturated fatty acids (C-12:0-C-30:0) and oleic acid (C-18:1) from southern Alaska since 1734 AD: A link to climate change in the Northern Hemisphere

Pokhrel Ambarish,Kawamura Kimitaka,Seki Osamu,Matoba Sumito,Shiraiwa Takayuki
Atmospheric environment 100, 202-209, 2015-01
… An ice core drilled at Aurora Peak in southeast Alaska was analyzed for homologous series of straight chain fatty acids (C-12:0-C-30:0) including unsaturated fatty acid (oleic acid) using gas chromatography (GC/FID) and GC/mass spectrometry (GC/MS). … Molecular distributions of fatty acids are characterized by even carbon number predominance with a peak at palmitic acid (C-16:0, av. 20.3 +/- SD. …
NAID 120005549589

Utilization of Stearic acid Extracted from Olive Pomace for Production of Triazoles, Thiadiazoles and Thiadiazines Derivatives of Potential Biological Activities

Soliman Hanaa Mohamad,Basuny Amany M.,Arafat Shaker M.
Journal of Oleo Science advpub(0), 2015
… These saturated fatty acids were identified by GC mass after esterification, and were identified as stearic, palmitic and myristic acids. … Stearic acid was extracted using supercritical CO2 extractor2). … The stearic acid was confirmed by means of GC mass after its esterification, and it was used as starting material for preparation of a variety of heterocyclic compounds, which were then tested for their antimicrobial activities. …
NAID 130005092020

Metabolomics changes in a rat model of obstructive jaundice: mapping to metabolism of amino acids, carbohydrates and lipids as well as oxidative stress

Long Yue,Dong Xin,Yuan Yawei,Huang Jinqiang,Song Jiangang,Sun Yumin,Lu Zhijie,Yang Liqun,Yu Weifeng
Journal of Clinical Biochemistry and Nutrition 57(1), 50-59, 2015
… >-glutamate, l-tyrosine, kynurenine, l-lactic acid, LysoPCc (14:0), glycine and succinic acid and decreased levels of l-valine, PCb (19:0/0:0), taurine, palmitic acid, l-isoleucine and citric acid metabolism …
NAID 130005085269

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★リンクテーブル★

リンク元	「palmitate」「パルミチン酸」「hexadecanoic acid」

「palmitate」

Palmitic acid
	IUPAC name hexadecanoic acid
	Other names C16:0 (Lipid numbers), palmic acid
Identifiers
CAS number	57-10-3
PubChem	985
ChEMBL	CHEMBL82293
IUPHAR ligand	1055
Jmol-3D images	Image 1
	SMILES CCCCCCCCCCCCCCCC(=O)O ;
Properties
Molecular formula	C16H32O2
Molar mass	256.42 g/mol
Appearance	White crystals
Density	0.853 g/cm3 at 62 °C
Melting point	62.9 °C
Boiling point	351-352 °C; 215 °C at 15 mmHg
Solubility in water	Insoluble
Acidity (pKa)	4.78
Hazards
NFPA 704	1 1 0
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references