パルミチン酸 化学特性,用途語,生産方法
外観
白色, 微粒又は粉末
定義
本品は、次の化学式で表される脂肪酸である。
溶解性
水に不溶。冷エタノールに難溶。エーテル, 熱エタノールに易溶。エーテルに溶けやすく、エタノールにやや溶けやすく、水にほとんど溶けない。水に不溶。エーテル、ベンゼン、クロロホルムに可溶。石油エーテルに難溶。ジエチルエーテルに溶けやすく、エタノールにやや溶けやすく、水にほとんど溶けない。
解説
[同義異語]パルミチン酸
森北出版「化学辞典（第2版）
用途
有機合成、化粧品、医薬品、油剤、石鹸。
用途
乳化剤、可塑剤、化粧品原料、有機合成
化粧品の成分用途
不透明化剤、乳化剤、洗浄剤、香料
効能
診断補助薬 (超音波造影剤)
説明
Palmitic acid is a kind of common saturated fatty acid of a 16-carbon backbone, which is contained in fats and waxes. It naturally exists in palm oil and palm kernel oil, and can also be found in butter, cheese, milk, meat, cocoa butter, soybean oil and sunflower oil. It can be produced by many kinds of plants and organisms. It can be used for the production of soap, cosmetics, and industrial mold release agents. It is also a food processing aid. It can also be used to produce cetyl alocohol which is useful in the production of detergents and cosmetics. Recently, it has been also used for the manufacture of a long-acting antipsychotic medication, paliperidone palmitate.
化学的特性
Palmitic acid occurs as white crystalline scales with a slight characteristic odor and taste. It is one of the most common saturated fatty acids found in animals and plants. It is a mixture of solid organic acids obtained from fats consisting chiefly of palmitic acid (C16H35O2) with varying amounts of stearic acid (C16H36O2). As its name tells us, it is found in palm oil but also in butter, cheese, milk and meat.
天然物の起源
Reported found in apple, beef fat, preferments of bread, celery, cheddar cheese, blue cheese, roquefort cheese,
other cheeses, roasted cocoa bean, cognac, country cured ham, essential oil of lemon, heated milk, essential oil of sweet orange, pork
fat, potato, black tea, tomato, banana, grapefruit juice, cranberry, guava, grapes, melon, papaya, pear, raspberry, strawberry, cinnamon,
ginger, saffron, milk powder, fatty fish, chicken, lamb, hop oil, beer, rum, whiskies, grape wines, peanut oil, popcorn, soybean,
coconut meat, avocado, cloudberry, plums, beans, mushroom, starfruit, marjoram, fenugreek, mango, tamarind, fig, kelp, cardamom,rice, prickly pear, dill, licorice, sake, buckwheat, corn oil, malt, wort, roasted chicory root, lemon balm, shrimp, crab, clam, scallop,
Chinese quince, pawpaw and sweet grass oil.
使用
Palmitic Acid is a common fatty acid found in plants and animals. The body converts excess carbohydrates into Palmitic Acid, thus Palmitic Acid is the first fatty acid produced during fatty acid synt
hesis as well as a precursor for longer fatty acids.
定義
ChEBI: Palmitic acid is a saturated long-chain fatty acid with a 16-carbon backbone. It is a metabolite found in the aging mouse brain. It is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat.
主な応用
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.
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.
調製方法
Palmitic acid occurs naturally in all animal fats as the glyceride,
palmitin, and in palm oil partly as the glyceride and partly
uncombined. Palmitic acid is most conveniently obtained from
olive oil after removal of oleic acid, or from Japanese beeswax.
Synthetically, palmitic acid may be prepared by heating cetyl
alcohol with soda lime to 270°C or by fusing oleic acid with
potassium hydrate.
応用例（製薬）
Palmitic acid is used in oral and topical pharmaceutical formulations.
Palmitic acid has been used in implants for sustained release
of insulin in rats.
生物学的応用
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. 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.
安全性プロファイル
A poison by intravenous route. A human skin irritant. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes
安全性
Palmitic acid is used in oral and topical pharmaceutical formulations
and is generally regarded as nontoxic and nonirritant at the
levels employed as an excipient. However, palmitic acid is reported
to be an eye and skin irritant at high levels and is poisonous by
intravenous administration.
LD
50 (mouse, IV): 57 mg/kg
貯蔵
The bulk material should be stored in a well-closed container in a
cool, dry, place.
純化方法
Purify palmitic acid by slow (overnight) recrystallisation from hexane. Some samples are also crystallised from acetone, EtOH or EtOAc. The crystals are kept in air to lose solvent, or are pumped dry of solvent on a vacuum line. [Iwahashi et al. J Chem Soc, Faraday Trans 1 81 973 1985, pK: White J Am Chem Soc 72 1858 1950, Beilstein 2 IV 1157.]
不和合性
Palmitic acid is incompatible with strong oxidizing agents and
bases.
規制状況(Regulatory Status)
GRAS listed. Included in the FDA Inactive Ingredients Database
(oral tablets). Included in nonparenteral medicines licensed in the
UK.
パルミチン酸 上流と下流の製品情報
原材料
準備製品