芳香单羧酸、二羧酸和三羧酸酯、芳香二羧酸酯、二羧酸酯、三羧酸酯或多元醇酯

R. M. David, R. H. Mckee, J. Butala, R. Barter, M. Kayser
{"title":"芳香单羧酸、二羧酸和三羧酸酯、芳香二羧酸酯、二羧酸酯、三羧酸酯或多元醇酯","authors":"R. M. David, R. H. Mckee, J. Butala, R. Barter, M. Kayser","doi":"10.1002/0471435139.TOX080","DOIUrl":null,"url":null,"abstract":"The simple aliphatic esters of benzoic acid are liquids used as solvents, flavors, or perfumes. The arylbenzoate benzyl is used as a miticide or plasticizer. In general, these compounds have a low order of toxicity. The primary effect expected from ingestion of moderate amounts of benzoates is gastrointestinal irritation, gastric pain, nausea, and vomiting. Available data indicate a low order of skin absorbability, and the undiluted materials may be either slight or moderate skin irritants. In rabbits, the degree of skin irritation caused by alkyl benzoates increases with an increase in molecular weight. \n \n \n \nThe salicylates are used as flavorants, perfumes, or analgesics. The most commonly used member of this class of compounds is methyl salicylate. Ingestion of relatively small quantities of methyl salicylate may cause severe, rapid-onset salicylate poisoning. \n \n \n \nThe lower alkyl esters of p- or 4-hydroxybenzoic acid (C1 to C4), also named the methyl-, ethyl-, propyl-, and butyl parabens, are high-boiling liquids that decompose on heating. They are widely used in the food, cosmetic, and pharmaceutical industries as preservatives, bacteristats, and fungistats. Parabens also have been used therapeutically for the treatment of moniliasis, a Candida albicans infection. \n \n \n \nBy the oral route, parabens are rapidly absorbed, metabolized, and excreted. The lower paraben homologues have low potential for acute or chronic systemic toxicity and are therefore approved as human food additives. \n \n \n \nThe cinnamates (phenyl acrylates, phenylpropenoic acid esters) are mainly used as fragrances in the perfume industry. The cinnamates appear to have low to moderate toxicity in mammals. In humans, dermal exposure to allyl cinnamate may cause skin irritation. \n \n \n \nSome p-aminobenzoic acid (PABA) esters occur naturally, since the free compound, PABA, is an intricate part of the vitamin B complex and is utilized for its synthesis. PABA esters exhibit a low order of acute toxicity in experimental animals. In humans, cases of methemoglobinemia after topical benzocaine or procaine use have been reported. Sunscreen agents containing PABA esters may occasionally produce allergic photosensitization. \n \n \n \nThe ortho-aminobenzoates (anthranilates) are less irritating and less likely to cause sensitization than the para-aminobenzoates, but have less therapeutic usefulness. They are used in some sunscreen lotions. Anthranilates have low toxicity potential. \n \n \n \nLong-chain fatty acids of glycerides may be replaced by one or more acetyl groups to produce mono-, di-, or triacetin. Acetins, propionates, and butyrates serve as food additives, solvents or plasticizers, and surface-active agents. Available evidence indicates that these agents exhibit a low order of toxicity. Normally, no irritant effects occur upon inhalation or direct dermal contact. \n \n \n \nThe higher glycerides of fatty acids with odd-numbered carbon chains (C5 to C11) are found naturally in very small quantities in diverse organisms, and the even-numbered (C12 to C24) esters are common nutritional constituents. They are used as emulsifiers for foods, industrial raw materials, or nonacid detergent components. Some toxicity data are available for the C5 and C8 compounds. The even-numbered C12 to C18 glycerides are nontoxic. \n \n \n \nLittle toxicological information is known about resorcinol esters compounds. \n \n \n \nGallates are chemically trihydroxybenzoic acid esters. They serve generally as antioxidants, and the propyl, octyl, and dodecyl gallates have been approved as food additives. The gallates exhibit low acute and chronic toxicity in experimental animals. The bulk of evidence suggests that they are not carcinogenic or teratogenic. \n \n \n \nOxalates, malonates, glutarates, and succinates are high-flash, high-boiling fluids. Oxalates and malonates are mainly used as solvents for resins or as chemical intermediates. The general industrial use of these materials has not been associated with any particular toxicity problem. Diethyl oxalate, which can exert typical local solvent and systemic effects, may present an exception. In humans, diethyl oxalate may cause irritation to skin and mucous membranes. \n \n \n \nChemical and physical property data for alkyl and alkoxy adipates, azelates, and sebacates are summarized. These compounds are important chemical intermediates and are used extensively as plasticizers. Some of these agents are used in food packaging materials. They possess low acute toxicities, and their irritant effects on the skin and eye are very slight. Available evidence suggests that the lower alkyl adipates (dimethyl, diethyl, dibutyl) are reproductive and/or fetal toxicants. \n \n \n \nMaleic acid esters (cis-2-butenoates), fumarates (trans-2-butenoates), and itaconates have been utilized as plasticizers, raw materials for chemical syntheses, or preservatives for fats and oils. \n \n \n \nThe esters of alkenyl dicarboxylic acids are of low acute toxicity. They have a tendency to cause skin or eye irritation in rabbits. Allergic dermatitis has occurred in humans exposed to dibutyl maleate. Subacute and chronic toxicity data for these compounds are limited. \n \n \n \nThe aromatic ortho-dicarboxylic acid (phthalate) esters are among the most important industrial chemicals. They are used as plasticizers for a variety of plastics; those of C8 and above are used to add flexibility to PVC. They also are used with vinyl and cellulose resins to lend toughness and flexibility. They are commonly used in wire and cable coverings, moldings, vinyl consumer products, and medical devices. Some low-molecular-weight phthalate esters (e.g., methyl, ethyl, and butyl) are used as industrial solvents rather than as plasticizers. Occasionally, these low-molecular-weight phthalates have applications for consumer products such as ink and lacquer. Physically, phthalates occur mainly in liquid form with high boiling ranges and very low vapor pressures, with both contributing to the high stability of these materials. \n \n \n \nThe biological responses to phthalate esters vary based on the alcohol side chain and the animal species tested. In general, phthalate esters have low potential for acute toxicity following oral, dermal, or inhalation exposure. They are nonirritating or slightly irritating to the skin and eyes, and they are not sensitizers. \n \n \nKeywords: \n \nBenzoates; \nSalicylates; \nParabens; \nHydroxybenzoates; \nCinnamates; \nAminobenzoates; \nGlycerol acetates; \nAcetins; \nPropionates; \nButylates; \nOxalates; \nMalonates; \nSuccinates; \nSulfosuccinates; \nGlutarates; \nAdipates; \nAzelates; \nSebacates; \nMaleates; \nFumarates; \nItaconates; \nPhthalates; \nGlycolates; \nTrimellitates","PeriodicalId":19820,"journal":{"name":"Patty's Toxicology","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2001-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"48","resultStr":"{\"title\":\"Esters of Aromatic Mono‐, Di‐, and Tricarboxylic Acids, Aromatic Diacids and Di‐, Tri‐, Or Polyalcohols\",\"authors\":\"R. M. David, R. H. Mckee, J. Butala, R. Barter, M. Kayser\",\"doi\":\"10.1002/0471435139.TOX080\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The simple aliphatic esters of benzoic acid are liquids used as solvents, flavors, or perfumes. The arylbenzoate benzyl is used as a miticide or plasticizer. In general, these compounds have a low order of toxicity. The primary effect expected from ingestion of moderate amounts of benzoates is gastrointestinal irritation, gastric pain, nausea, and vomiting. Available data indicate a low order of skin absorbability, and the undiluted materials may be either slight or moderate skin irritants. In rabbits, the degree of skin irritation caused by alkyl benzoates increases with an increase in molecular weight. \\n \\n \\n \\nThe salicylates are used as flavorants, perfumes, or analgesics. The most commonly used member of this class of compounds is methyl salicylate. Ingestion of relatively small quantities of methyl salicylate may cause severe, rapid-onset salicylate poisoning. \\n \\n \\n \\nThe lower alkyl esters of p- or 4-hydroxybenzoic acid (C1 to C4), also named the methyl-, ethyl-, propyl-, and butyl parabens, are high-boiling liquids that decompose on heating. They are widely used in the food, cosmetic, and pharmaceutical industries as preservatives, bacteristats, and fungistats. Parabens also have been used therapeutically for the treatment of moniliasis, a Candida albicans infection. \\n \\n \\n \\nBy the oral route, parabens are rapidly absorbed, metabolized, and excreted. The lower paraben homologues have low potential for acute or chronic systemic toxicity and are therefore approved as human food additives. \\n \\n \\n \\nThe cinnamates (phenyl acrylates, phenylpropenoic acid esters) are mainly used as fragrances in the perfume industry. The cinnamates appear to have low to moderate toxicity in mammals. In humans, dermal exposure to allyl cinnamate may cause skin irritation. \\n \\n \\n \\nSome p-aminobenzoic acid (PABA) esters occur naturally, since the free compound, PABA, is an intricate part of the vitamin B complex and is utilized for its synthesis. PABA esters exhibit a low order of acute toxicity in experimental animals. In humans, cases of methemoglobinemia after topical benzocaine or procaine use have been reported. Sunscreen agents containing PABA esters may occasionally produce allergic photosensitization. \\n \\n \\n \\nThe ortho-aminobenzoates (anthranilates) are less irritating and less likely to cause sensitization than the para-aminobenzoates, but have less therapeutic usefulness. They are used in some sunscreen lotions. Anthranilates have low toxicity potential. \\n \\n \\n \\nLong-chain fatty acids of glycerides may be replaced by one or more acetyl groups to produce mono-, di-, or triacetin. Acetins, propionates, and butyrates serve as food additives, solvents or plasticizers, and surface-active agents. Available evidence indicates that these agents exhibit a low order of toxicity. Normally, no irritant effects occur upon inhalation or direct dermal contact. \\n \\n \\n \\nThe higher glycerides of fatty acids with odd-numbered carbon chains (C5 to C11) are found naturally in very small quantities in diverse organisms, and the even-numbered (C12 to C24) esters are common nutritional constituents. They are used as emulsifiers for foods, industrial raw materials, or nonacid detergent components. Some toxicity data are available for the C5 and C8 compounds. The even-numbered C12 to C18 glycerides are nontoxic. \\n \\n \\n \\nLittle toxicological information is known about resorcinol esters compounds. \\n \\n \\n \\nGallates are chemically trihydroxybenzoic acid esters. They serve generally as antioxidants, and the propyl, octyl, and dodecyl gallates have been approved as food additives. The gallates exhibit low acute and chronic toxicity in experimental animals. The bulk of evidence suggests that they are not carcinogenic or teratogenic. \\n \\n \\n \\nOxalates, malonates, glutarates, and succinates are high-flash, high-boiling fluids. Oxalates and malonates are mainly used as solvents for resins or as chemical intermediates. The general industrial use of these materials has not been associated with any particular toxicity problem. Diethyl oxalate, which can exert typical local solvent and systemic effects, may present an exception. In humans, diethyl oxalate may cause irritation to skin and mucous membranes. \\n \\n \\n \\nChemical and physical property data for alkyl and alkoxy adipates, azelates, and sebacates are summarized. These compounds are important chemical intermediates and are used extensively as plasticizers. Some of these agents are used in food packaging materials. They possess low acute toxicities, and their irritant effects on the skin and eye are very slight. Available evidence suggests that the lower alkyl adipates (dimethyl, diethyl, dibutyl) are reproductive and/or fetal toxicants. \\n \\n \\n \\nMaleic acid esters (cis-2-butenoates), fumarates (trans-2-butenoates), and itaconates have been utilized as plasticizers, raw materials for chemical syntheses, or preservatives for fats and oils. \\n \\n \\n \\nThe esters of alkenyl dicarboxylic acids are of low acute toxicity. They have a tendency to cause skin or eye irritation in rabbits. Allergic dermatitis has occurred in humans exposed to dibutyl maleate. Subacute and chronic toxicity data for these compounds are limited. \\n \\n \\n \\nThe aromatic ortho-dicarboxylic acid (phthalate) esters are among the most important industrial chemicals. 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引用次数: 48

摘要

苯甲酸的简单脂肪族酯是用作溶剂、香精或香水的液体。芳基苯甲酸苄酯用作杀虫剂或增塑剂。一般来说,这些化合物的毒性较低。摄入适量苯甲酸盐的主要作用是胃肠道刺激、胃痛、恶心和呕吐。现有数据表明,皮肤可吸收性较低,未稀释的材料可能对皮肤有轻微或中度刺激。在家兔中,烷基苯甲酸酯引起的皮肤刺激程度随着分子量的增加而增加。水杨酸盐可用作香料、香水或止痛剂。这类化合物中最常用的成员是水杨酸甲酯。摄入相对少量的水杨酸甲酯可引起严重的、快速发作的水杨酸中毒。对羟基苯甲酸或4-羟基苯甲酸(C1至C4)的低烷基酯,也被称为对羟基苯甲酸甲酯、乙基苯甲酸酯、丙基苯甲酸酯和丁基苯甲酸酯,是加热时分解的高沸点液体。它们广泛用于食品、化妆品和制药行业,作为防腐剂、抑菌剂和真菌剂。对羟基苯甲酸酯也用于治疗念珠菌感染念珠菌病。通过口服途径,对羟基苯甲酸酯被迅速吸收、代谢和排泄。较低的对羟基苯甲酸酯同系物具有较低的急性或慢性全身毒性,因此被批准作为人类食品添加剂。肉桂酸酯(苯基丙烯酸酯、苯基丙烯酸酯)在香水工业中主要用作香料。肉桂酸酯对哺乳动物似乎有低到中等的毒性。在人类,皮肤暴露于肉桂酸烯丙酯可能会引起皮肤刺激。一些对氨基苯甲酸(PABA)酯自然产生,因为游离化合物PABA是维生素B复合物的一个复杂部分,并用于其合成。PABA酯类在实验动物中表现出低阶急性毒性。在人类中,局部使用苯佐卡因或普鲁卡因后出现高铁血红蛋白血症的病例已有报道。含有PABA酯的防晒剂偶尔会产生过敏性光敏。邻氨基苯甲酸酯(邻氨基苯甲酸酯)比对氨基苯甲酸酯刺激性更小,引起致敏的可能性更小,但治疗效果较差。它们被用于一些防晒乳液中。邻氨基苯甲酸酯具有低毒性。甘油酯的长链脂肪酸可被一个或多个乙酰基取代,生成单乙酰、二乙酰或三乙酰。醋酸酯、丙酸酯和丁酸酯用作食品添加剂、溶剂或增塑剂以及表面活性剂。现有证据表明,这些药剂的毒性较低。通常情况下,吸入或直接皮肤接触不会产生刺激性作用。奇数碳链脂肪酸(C5至C11)的高甘油酯自然存在于各种生物体中,数量很少,偶数(C12至C24)酯是常见的营养成分。它们被用作食品、工业原料或非酸性洗涤剂的乳化剂。一些关于C5和C8化合物的毒性数据是可用的。偶数的C12到C18甘油是无毒的。间苯二酚酯类化合物的毒理学信息很少。没食子酸盐在化学上是三羟基苯甲酸酯。它们通常用作抗氧化剂,而没食子酸酯丙酯、没食子酸酯辛酯和没食子酸酯十二烷基已被批准作为食品添加剂。没食子酸酯在实验动物中表现出较低的急性和慢性毒性。大量证据表明它们不会致癌或致畸。草酸盐、丙二酸盐、戊二酸盐和琥珀酸盐是高闪、高沸腾的液体。草酸盐和丙二酸盐主要用作树脂的溶剂或化学中间体。这些材料的一般工业用途没有与任何特定的毒性问题联系在一起。草酸二乙酯可以发挥典型的局部溶剂和全身效应,可能是一个例外。对人类来说,草酸二乙酯可能会刺激皮肤和粘膜。综述了烷基和烷氧己二酸酯、氮二酸酯和癸二酸酯的化学和物理性质数据。这些化合物是重要的化学中间体,广泛用作增塑剂。其中一些药剂用于食品包装材料。它们具有低急性毒性,对皮肤和眼睛的刺激作用非常轻微。现有证据表明,较低的烷基己二酸酯(二甲基、二乙基、二丁基)是生殖和/或胎儿毒物。马来酸酯(顺式-2-丁烯酸酯)、富马酸酯(反式-2-丁烯酸酯)和邻戊酸酯已被用作增塑剂、化学合成原料或脂肪和油的防腐剂。烯基二羧酸酯具有低急性毒性。 它们有引起兔子皮肤或眼睛刺激的倾向。接触马来酸二丁酯的人也发生过过敏性皮炎。这些化合物的亚急性和慢性毒性数据有限。邻苯二甲酸(邻苯二甲酸酯)是最重要的工业化学品之一。它们被用作各种塑料的增塑剂;C8及以上的用于增加PVC的柔韧性。它们还与乙烯基和纤维素树脂一起使用,以增加韧性和柔韧性。它们通常用于电线电缆外壳,模具,乙烯基消费品和医疗设备。一些低分子量邻苯二甲酸酯(如甲基、乙基和丁基)用作工业溶剂而不是增塑剂。偶尔,这些低分子量邻苯二甲酸盐有应用于消费品,如油墨和漆。物理上,邻苯二甲酸盐主要以液体形式存在,具有高沸点范围和非常低的蒸汽压,这两者都有助于这些材料的高稳定性。邻苯二甲酸酯的生物反应因醇侧链和实验动物种类而异。一般来说,邻苯二甲酸酯在口服、皮肤或吸入暴露后发生急性毒性的可能性很低。它们对皮肤和眼睛没有刺激或轻微刺激,它们不是致敏剂。关键词:苯甲酸;水杨酸盐;防腐剂;Hydroxybenzoates;肉桂酸;Aminobenzoates;丙三醇醋酸盐;醋精;类;丁醇;草酸;丙二酸酯;琥珀酸;Sulfosuccinates;戊二酸;己二酸;壬二;癸二酸酯;顺丁烯二酸盐;延胡索酸酯;Itaconates;邻苯二甲酸酯;羧甲;Trimellitates
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Esters of Aromatic Mono‐, Di‐, and Tricarboxylic Acids, Aromatic Diacids and Di‐, Tri‐, Or Polyalcohols
The simple aliphatic esters of benzoic acid are liquids used as solvents, flavors, or perfumes. The arylbenzoate benzyl is used as a miticide or plasticizer. In general, these compounds have a low order of toxicity. The primary effect expected from ingestion of moderate amounts of benzoates is gastrointestinal irritation, gastric pain, nausea, and vomiting. Available data indicate a low order of skin absorbability, and the undiluted materials may be either slight or moderate skin irritants. In rabbits, the degree of skin irritation caused by alkyl benzoates increases with an increase in molecular weight. The salicylates are used as flavorants, perfumes, or analgesics. The most commonly used member of this class of compounds is methyl salicylate. Ingestion of relatively small quantities of methyl salicylate may cause severe, rapid-onset salicylate poisoning. The lower alkyl esters of p- or 4-hydroxybenzoic acid (C1 to C4), also named the methyl-, ethyl-, propyl-, and butyl parabens, are high-boiling liquids that decompose on heating. They are widely used in the food, cosmetic, and pharmaceutical industries as preservatives, bacteristats, and fungistats. Parabens also have been used therapeutically for the treatment of moniliasis, a Candida albicans infection. By the oral route, parabens are rapidly absorbed, metabolized, and excreted. The lower paraben homologues have low potential for acute or chronic systemic toxicity and are therefore approved as human food additives. The cinnamates (phenyl acrylates, phenylpropenoic acid esters) are mainly used as fragrances in the perfume industry. The cinnamates appear to have low to moderate toxicity in mammals. In humans, dermal exposure to allyl cinnamate may cause skin irritation. Some p-aminobenzoic acid (PABA) esters occur naturally, since the free compound, PABA, is an intricate part of the vitamin B complex and is utilized for its synthesis. PABA esters exhibit a low order of acute toxicity in experimental animals. In humans, cases of methemoglobinemia after topical benzocaine or procaine use have been reported. Sunscreen agents containing PABA esters may occasionally produce allergic photosensitization. The ortho-aminobenzoates (anthranilates) are less irritating and less likely to cause sensitization than the para-aminobenzoates, but have less therapeutic usefulness. They are used in some sunscreen lotions. Anthranilates have low toxicity potential. Long-chain fatty acids of glycerides may be replaced by one or more acetyl groups to produce mono-, di-, or triacetin. Acetins, propionates, and butyrates serve as food additives, solvents or plasticizers, and surface-active agents. Available evidence indicates that these agents exhibit a low order of toxicity. Normally, no irritant effects occur upon inhalation or direct dermal contact. The higher glycerides of fatty acids with odd-numbered carbon chains (C5 to C11) are found naturally in very small quantities in diverse organisms, and the even-numbered (C12 to C24) esters are common nutritional constituents. They are used as emulsifiers for foods, industrial raw materials, or nonacid detergent components. Some toxicity data are available for the C5 and C8 compounds. The even-numbered C12 to C18 glycerides are nontoxic. Little toxicological information is known about resorcinol esters compounds. Gallates are chemically trihydroxybenzoic acid esters. They serve generally as antioxidants, and the propyl, octyl, and dodecyl gallates have been approved as food additives. The gallates exhibit low acute and chronic toxicity in experimental animals. The bulk of evidence suggests that they are not carcinogenic or teratogenic. Oxalates, malonates, glutarates, and succinates are high-flash, high-boiling fluids. Oxalates and malonates are mainly used as solvents for resins or as chemical intermediates. The general industrial use of these materials has not been associated with any particular toxicity problem. Diethyl oxalate, which can exert typical local solvent and systemic effects, may present an exception. In humans, diethyl oxalate may cause irritation to skin and mucous membranes. Chemical and physical property data for alkyl and alkoxy adipates, azelates, and sebacates are summarized. These compounds are important chemical intermediates and are used extensively as plasticizers. Some of these agents are used in food packaging materials. They possess low acute toxicities, and their irritant effects on the skin and eye are very slight. Available evidence suggests that the lower alkyl adipates (dimethyl, diethyl, dibutyl) are reproductive and/or fetal toxicants. Maleic acid esters (cis-2-butenoates), fumarates (trans-2-butenoates), and itaconates have been utilized as plasticizers, raw materials for chemical syntheses, or preservatives for fats and oils. The esters of alkenyl dicarboxylic acids are of low acute toxicity. They have a tendency to cause skin or eye irritation in rabbits. Allergic dermatitis has occurred in humans exposed to dibutyl maleate. Subacute and chronic toxicity data for these compounds are limited. The aromatic ortho-dicarboxylic acid (phthalate) esters are among the most important industrial chemicals. They are used as plasticizers for a variety of plastics; those of C8 and above are used to add flexibility to PVC. They also are used with vinyl and cellulose resins to lend toughness and flexibility. They are commonly used in wire and cable coverings, moldings, vinyl consumer products, and medical devices. Some low-molecular-weight phthalate esters (e.g., methyl, ethyl, and butyl) are used as industrial solvents rather than as plasticizers. Occasionally, these low-molecular-weight phthalates have applications for consumer products such as ink and lacquer. Physically, phthalates occur mainly in liquid form with high boiling ranges and very low vapor pressures, with both contributing to the high stability of these materials. The biological responses to phthalate esters vary based on the alcohol side chain and the animal species tested. In general, phthalate esters have low potential for acute toxicity following oral, dermal, or inhalation exposure. They are nonirritating or slightly irritating to the skin and eyes, and they are not sensitizers. Keywords: Benzoates; Salicylates; Parabens; Hydroxybenzoates; Cinnamates; Aminobenzoates; Glycerol acetates; Acetins; Propionates; Butylates; Oxalates; Malonates; Succinates; Sulfosuccinates; Glutarates; Adipates; Azelates; Sebacates; Maleates; Fumarates; Itaconates; Phthalates; Glycolates; Trimellitates
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