関: palmitate、palmitic acid

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）』「2015/07/19 14:38:38」(JST)

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Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common fatty acid (saturated) found in animals, plants and microorganisms.^[9] Its chemical formula is CH₃(CH₂)₁₄COOH. As its name indicates, it is a major component of the oil from palm trees (palm 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 physiologic pH (7.4).

Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. 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.^[10] 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 or 390 °F), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled.^[11]

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. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to comprise 21–30% (molar) of human depot fat,^[12] and it is a major, but highly variable, lipid component of human breast milk.^[13] 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.^[14] 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 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 palm tree (species Elaeis Guineensis), 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.^[15] The aluminium salt is used as a thickening agent of napalm used in military actions.

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.

Health effects

According to the World Health Organization, evidence is "convincing" that consumption of palmitic acid increases risk of developing cardiovascular diseases.^[16] 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.

Rats fed a diet of 20% palmitic acid and 80% carbohydrate for extended periods showed alterations in central nervous system control of insulin secretion, and suppression of the body's natural appetite-suppressing signals from leptin and insulin (the key hormones involved in weight regulation).^[17]

References

^ Merck Index, 12th Edition, 7128.
^ ^a ^b ^c ^d ^e ^f Sigma-Aldrich Co., Palmitic acid. Retrieved on 2014-06-02.
^ ^a ^b ^c ^d ^e ^f CID 985 from PubChem
^ Palmitic acid at Inchem.org
^ ^a ^b ^c ^d http://chemister.ru/Database/properties-en.php?dbid=1&id=6488
^ Seidell, Atherton; Linke, William F. (1952). [Google Books Solubilities of Inorganic and Organic Compounds]. Van Nostrand. Retrieved 2014-06-02.
^ ^a ^b ^c ^d n-Hexadecanoic 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 2014-05-11)
^ 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.
^ 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
^ Frémy, E. (1842). "Memoire sur les produits de la saponification de l’huile de palme". Journal de Pharmacie et de Chimie XII: 757.
^ Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_245.pub2.
^ Kingsbury, K. J.; Paul, S.; Crossley, A.; Morgan, D. M. (1961). "The fatty acid composition of human depot fat". Biochemical Journal 78: 541–550. PMC 1205373. PMID 13756126.
^ Lipids of human milk and infant formulas: a review
^ 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)
^ Benoit SC, Kemp CJ, Elias CF, Abplanalp W, Herman JP, Migrenne S, Lefevre AL, Cruciani-Guglielmacci C, Magnan C, Yu F, Niswender K, Irani BG, Holland WL, Clegg DJ (2009). "Palmitic acid mediates hypothalamic insulin resistance by altering PKC-θ subcellular localization in rodents". Journal of Clinical Investigation 119 (9): 2577–2587. doi:10.1172/JCI36714. PMID 19726875.

External links

Media related to Palmitic acid at Wikimedia Commons

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English Journal

Lipolysis and lipid oxidation during processing of Chinese traditional smoke-cured bacon.

Huang Y, Li H, Huang T, Li F, Sun J.Author information College of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, PR China. Electronic address: hyc2005@sina.com.AbstractLipolysis and lipid oxidation as well as the relationship between them during processing of Chinese traditional smoke-cured bacon were studied by evaluating the changes in physicochemical parameters, lipase and lipoxygenase (LOX) activities, lipid content, fatty acid composition, peroxide value (POV), and thiobarbituric acid reactive substances (TBARS). Besides phospholipids, triacylglycerols (TAG) were an important source of free fatty acids in bacon, resulting in an increase in free fatty acid content in the mid-late stage of processing, whilst phospholipids hydrolysed intensely in the early stage. Preferential lipolysis was observed for polyunsaturated fatty acids in phospholipids and for linoleic and palmitic acids in TAG. The lipolysis of TAG and phospholipids was independent and catalysed by acid lipase and phospholipase, respectively. ANOVA-partial least squares regression (APLSR) analysis showed that POV and TBARS were poorly related to LOX and closely associated with phospholipid degradation. Therefore, autoxidation may be the main cause of muscle lipid oxidation in smoke-cured bacon, which was promoted by phospholipid hydrolysis.
Food chemistry.Food Chem.2014 Apr 15;149:31-9. doi: 10.1016/j.foodchem.2013.10.081. Epub 2013 Oct 26.
Lipolysis and lipid oxidation as well as the relationship between them during processing of Chinese traditional smoke-cured bacon were studied by evaluating the changes in physicochemical parameters, lipase and lipoxygenase (LOX) activities, lipid content, fatty acid composition, peroxide value (POV
PMID 24295673

Carotenoid composition of berries and leaves from six Romanian sea buckthorn (Hippophae rhamnoides L.) varieties.

Pop RM, Weesepoel Y, Socaciu C, Pintea A, Vincken JP, Gruppen H.Author information University of Agricultural Sciences and Veterinary Medicine, Mănăştur Street, 3-5, 400372 Cluj-Napoca, Romania; Laboratory of Food Chemistry, Wageningen University, P.O. Box 8129, 6700 EV Wageningen, The Netherlands.AbstractBerries and leaves from six varieties of Carpathians' sea buckthorn (Hippophae rhamnoides L., ssp. Carpatica) were analysed for their carotenoid composition (free and esterified) using a combination of HPLC-PAD, GC-MS and UHPLC-PAD-ESI-MS techniques. GC-MS techniques revealed the fatty acid profile specific for each berry variety, while targeted UHPLC-MS analysis identified the fatty acids involved in carotenoids esterification: palmitic (C16:0), myristic (C14:0) and stearic (C18:0). Total carotenoid content varied between 53 and 97 mg/100g dry weight in berries, and between 3.5 and 4.2mg/100g DW in leaves. The carotenoid di-esters represented the main fraction among berry varieties having zeaxanthin di-palmitate as major compound, while leaves contained only free carotenoids like lutein, β-carotene, violaxanthin and neoxanthin. Principal component analysis identified the suitable carotenoid biomarkers characteristic for the Carpathians' sea buckthorn from Romania with contribution to their taxonomic classification and authenticity recognition.
Food chemistry.Food Chem.2014 Mar 15;147:1-9. doi: 10.1016/j.foodchem.2013.09.083. Epub 2013 Sep 27.
Berries and leaves from six varieties of Carpathians' sea buckthorn (Hippophae rhamnoides L., ssp. Carpatica) were analysed for their carotenoid composition (free and esterified) using a combination of HPLC-PAD, GC-MS and UHPLC-PAD-ESI-MS techniques. GC-MS techniques revealed the fatty acid profile
PMID 24206678

Methods of analysis for 2-dodecylcyclobutanone and studies to support its role as a unique marker of food irradiation.

Driffield M, Speck D, Lloyd AS, Parmar M, Crews C, Castle L, Thomas C.Author information The Food and Environment Research Agency, Sand Hutton, York YO41 1LZ, UK. Electronic address: malcolm.driffield@fera.gsi.gov.uk.AbstractMethods of analysis for 2-dodecylcyclobutanone (2-DCB) using gas chromatography with mass spectrometric detection (GC-MS), liquid chromatography with time-of-flight mass spectrometric detection (LC-TOF-MS) and LC with tandem MS (MS/MS) detection have been developed and optimised for maximum sensitivity to allow very low irradiation doses to be detected. The LC-MS/MS method, following derivatisation with 2,4-dinitrophenylhydrazine, was found to be the most sensitive technique and was used to determine the amount of 2-DCB formed from the model compounds palmitic acid, glyceryl tripalmitate and 1,3-dipalmitoyl-2-oleoylglycerol irradiated over a range of doses by two different irradiation sources (gamma and electron beam). The model compounds were also treated with a number of non-irradiation based processing techniques including heating in the presence and absence of oxygen, light, and redox active metal salts, in a conventional oven, microwave oven and pressure cooker. No 2-DCB was detected in any of the processed non-irradiated model compounds, reaffirming the hypothesis that 2-DCB is a unique radiolytic product that can be used as a marker of irradiation in foodstuffs.
Food chemistry.Food Chem.2014 Mar 1;146:308-13. doi: 10.1016/j.foodchem.2013.09.046. Epub 2013 Sep 18.
Methods of analysis for 2-dodecylcyclobutanone (2-DCB) using gas chromatography with mass spectrometric detection (GC-MS), liquid chromatography with time-of-flight mass spectrometric detection (LC-TOF-MS) and LC with tandem MS (MS/MS) detection have been developed and optimised for maximum sensitiv
PMID 24176347

Japanese Journal

Serum Metabolomics in Rats after Acute Paraquat Poisoning

Biological and Pharmaceutical Bulletin 38(7), 1049-1053, 2015
NAID 130005086291

DPPH Scavenging, PRAP Activities and Essential Oil Composition of Edible <i>Lathyrus ochrus</i> L. (Cyprus Vetch, Luvana) from Cyprus

Journal of Oleo Science advpub(0), 2015
NAID 130004800133

DPPH Scavenging, PRAP Activities and Essential Oil Composition of Edible <i>Lathyrus ochrus</i> L. (Cyprus Vetch, Luvana) from Cyprus

Journal of Oleo Science 64(3), 309-314, 2015
NAID 130004800117

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★リンクテーブル★

リンク元	「palmitate」「パルミチン酸」「ヘキサデカン酸」
拡張検索	「3,7,11,15-tetramethylhexadecanoic acid」

「palmitate」

Palmitic acid^[1]
Names
	IUPAC name hexadecanoic acid
	Other names C16:0 (Lipid numbers), palmic acid
Identifiers
CAS Registry Number	57-10-3
ChEMBL	ChEMBL82293
ChemSpider	960
	InChI InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) ; Key: IPCSVZSSVZVIGE-UHFFFAOYSA-N ; InChI=1/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18); Key: IPCSVZSSVZVIGE-UHFFFAOYAJ ;
IUPHAR/BPS	1055
Jmol-3D images	Image
PubChem	985
	SMILES CCCCCCCCCCCCCCCC(=O)O ;
Properties
Chemical formula	C16H32O2
Molar mass	256.43 g·mol−1
Appearance	white crystals
Density	0.852 g/cm3 (25 °C); 0.8527 g/cm3 (62 °C)
Melting point	62.9 °C (145.2 °F; 336.0 K)
Boiling point	351–352 °C (664–666 °F; 624–625 K) ; 271.5 °C (520.7 °F; 544.6 K); at 100 mmHg; 215 °C (419 °F; 488 K); at 15 mmHg
Solubility in water	4.6 mg/L (0 °C); 7.19 mg/L (20 °C); 8.26 mg/L (30 °C); 9.9 mg/L (45 °C); 11.8 mg/L (60 °C)
Solubility	soluble in amyl acetate, alcohol, CCl4, C6H6; very soluble in CHCl3
Solubility in ethanol	2 g/100 mL (0 °C); 2.8 g/100 mL (10 °C); 9.2 g/100 mL (20 °C); 31.9 g/100 mL (40 °C)
Solubility in methyl acetate	7.81 g/100 g
Solubility in ethyl acetate	10.7 g/100 g
Vapor pressure	0.051 mPa (25 °C); 1.08 kPa (200 °C); 28.06 kPa (300 °C)
Acidity (pKa)	4.78
Refractive index (nD)	1.43 (70 °C)
Thermochemistry
Specific; heat capacity (C)	463.36 J/mol·K
Std molar; entropy (So298)	452.37 J/mol·K
Std enthalpy of; formation (ΔfHo298)	-892 kJ/mol
Std enthalpy of; combustion (ΔcHo298)	10030.6 kJ/mol
Hazards
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H319
GHS precautionary statements	P305+351+338
EU classification	Xi
R-phrases	R36/37/38
S-phrases	S26
NFPA 704	1 1 0
Flash point	206 °C (403 °F; 479 K)
	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