4-ヒドロキシ安息香酸 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶性粉末～粉末
溶解性
エタノール及びアセトンに溶け、水に溶けにくい。(水:0.8W%)
用途
生体内ではユビキノン合成などの中間体として重要であり、動物、植物、微生物を含め幅広い生物が合成している。したがって食品中にも存在しており、ココナツやアサイーなどには多く含まれている。4-ヒドロキシ安息香酸のエステルはパラベンと呼ばれ、保存料として用いられる。4-ヒドロキシ安息香酸はその原料である。
用途
有機合成原料。
説明
4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid or PHBA, is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohol and acetone. It is isomeric with salicylic acid (2-hydroxybenzoic acid), a forerunner to aspirin, and 3-hydroxybenzoic acid. The esters of 4-hydroxybenzoic acid, also called parabens, are widely used as preservatives in cosmetics and some ophthalmic solutions.
化学的特性
4-Hydroxybenzoic acid is an odorless white crystalline astringent powder. In pure form, it imparts a sweetish taste at
first, which quickly becomes acrid and disagreeable
天然物の起源
4-Hydroxybenzoic acid is a phenolic acid that has been found in a variety of fruit peels and leaves. It can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in Macrotyloma uniflorum (horse gram), carob and in Phyllanthus acidus (Otaheite gooseberry).
使用
4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4'-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions.
製造方法
Prepared from p-bromophenol or p-hydroxybenzaldehyde, or from saponification of methyl salicylate, a major component
of oil of wintergreen.
In 1947, H. Gilman and C. E. Arntzen at Iowa State College (Ames) reported the synthesis of 4-HBA from 4-hydroxybenzaldehyde. Several other preparation methods were developed since then. Today it is produced commercially via the Kolbe–Schmitt reaction, which originated in the mid-1800s. Potassium phenoxide and CO2 are heated under pressure; the reaction mixture is then acidified to obtain the product 4-Hydroxybenzoic acid. (Oddly, if the sodium salt is used, the product is 2-hydroxybenzoic acid, or salicylic acid.)
Org. Synth. 1934, 14, 48
DOI:
10.15227/orgsyn.014.0048
定義
ChEBI: 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate.
主な応用
4-Hydroxybenzoic acid can be used as a starting material to synthesize organic intermediates such as 4-acetoxybenzoic acid and 4-hydroxy-3,5-diiodobenzoic acid.
4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4′-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions.
一般的な説明
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. 4-Hydroxybenzoic acid belongs to the class of aromatic acids, which may be used as a preservative in cosmetics, pharmaceuticals and as a synthetic flavoring agent in food products.
純化方法
Crystallise the hydroxyacid from water. [Beilstein 10 IV 345.]
4-ヒドロキシ安息香酸 上流と下流の製品情報
原材料
準備製品