苯甲酸钠
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苯甲酸钠 | |
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IUPAC名 Sodium benzoate | |
别名 | E211、苯酸钠、安息香酸钠、苯甲酸钠盐 |
识别 | |
CAS号 | 532-32-1 ![]() |
PubChem | 517055 |
ChemSpider | 10305 |
SMILES |
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InChI |
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InChIKey | WXMKPNITSTVMEF-REWHXWOFAY |
ChEBI | 113455 |
RTECS | DH6650000 |
性质 | |
化学式 | C7H5NaO2 |
摩尔质量 | 144.1 g·mol−1 |
外观 | 白色或无色结晶粉末 |
气味 | 无味 |
密度 | 1.497 g/cm3 |
熔点 | 410 °C(683 K) |
溶解性(水) | 62.65 g/100 mL(0 °C) 62.84 g/100 mL(15 °C) 62.87 g/100 mL(30 °C) 74.2 g/100 mL(100 °C)[1] |
溶解性 | 溶于液氨、吡啶[1] |
溶解性(甲醇) | 8.22 g/100 g(15 °C) 7.55 g/100 g(66.2 °C)[1] |
溶解性(乙醇) | 2.3 g/100 g(25 °C) 8.3 g/100 g(78 °C)[1] |
溶解性(1,4-二𫫇英) | 0.818 mg/kg(25 °C)[1] |
药理学 | |
ATC代码 | A16AX11(A16) |
危险性 | |
GHS危险性符号![]() | |
GHS提示词 | Warning |
H-术语 | H319[2] |
P-术语 | P305+351+338[2] |
NFPA 704 | |
致死量或浓度: | |
LD50(中位剂量)
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4100 mg/kg(大鼠,口服) |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
苯甲酸钠是苯甲酸的钠盐,化学式为C
6H
5CO
2Na,是一种白色结晶固体。苯甲酸钠是很常用的食品防腐剂,E编码为E211。
自然产生
许多植物是苯甲酸及其盐和酯的天然来源,尤其是蔓越莓和覆盆子等浆果。[3]
生产
用途
防腐剂
苯甲酸钠可用作防腐剂。它最广泛用于酸性食品,如沙拉酱、碳酸饮料、果酱和果汁、泡菜、调味料和冻酸奶。在药品和化妆品中也用作防腐剂。[5][6]在酸性条件下能转化为苯甲酸,具有抑菌作用。苯甲酸水溶性差,一般不直接使用。美国FDA将其作为食品防腐剂的浓度限制为0.1%(按重量计)。[7]根据美国饲料控制官员协会的规定,苯甲酸钠也被允许用作动物食品添加剂,最高含量为0.1%。[8]在英国,大多数软饮料中的苯甲酸钠已被山梨酸钾取代。[9]
药物
苯甲酸钠因其结合氨基酸的能力而被用作尿素循环障碍的治疗药物。[10][11]最近的研究表明,苯甲酸钠作为附加疗法(1g/天)可能对精神分裂症有益。[12][13][14]
苯甲酸钠与咖啡因一起用于治疗硬膜穿刺后头痛、与吸毒过量导致的呼吸抑制,[17][18]并与麦角胺一起治疗血管性头痛。[19]
机制
苯甲酸钠的防腐机制为:苯甲酸亲油性较强,容易穿过细胞膜进入细胞内,干扰细菌和霉菌等微生物细胞膜的通透性,抑制细胞膜对氨基酸的吸收。进入细胞内的苯甲酸分子抑制微生物细胞呼吸酶系的活性,使无氧呼吸中磷酸果糖激酶催化的反应速率下降95%,从而起到防腐作用。[20]
对健康的影响
苯甲酸/苯甲酸盐天然存在于蓝莓、蔓越莓、梅干、肉桂和丁香[哪个/哪些?]中。少量的苯甲酸钠对人体无毒害,它可以在体内很快被吸收,主要与甘氨酸结合以马尿酸的形式排出体外,也有一小部分与葡糖醛酸结合为1-苯甲酰葡糖醛酸而排出。10-14小时便可从体内全部排出,因此少量的苯甲酸钠不会有积蓄作用。但是猫对苯甲酸比较敏感,过量摄取容易出现兴奋、神经过敏、失去听力和平衡等症状,因此在制造宠物食品时需注意,但少量摄取并不影响健康。[21][22]
FDA规定食品中的苯甲酸钠含量不得超过0.1%(以重量计)。[23]国际化学品安全署的研究发现每天摄入647-835mg每千克体重的苯甲酸钠不会对健康产生负面影响。[24][25]
苯甲酸盐类防腐剂(苯甲酸钠、苯甲酸钾)可以与维生素C反应生成具有致癌性的苯,[26]尤其在柑橘类饮料中更容易存在,(Sadighara et al., 2022)[27]。由于各国对于饮料中苯的含量标准不一,不同的饮料中苯的含量也不相同,而且上述分解反应也与光照、加热和储存时间等诸多因素有很大关系,因此目前对苯甲酸盐产生的苯是否超标没有定论。这使得公众对苯甲酸盐毒性的质疑持续不断。可口可乐公司因此宣布将在其产品中逐渐禁止苯甲酸钠的使用,而用更加天然的防腐剂代替。[28]但用另一种抗氧化剂代替抗坏血酸,添加 EDTA 或聚磷酸钠以螯合催化羟基自由基形成的金属离子,并审查储存条件和保质期以尽量减少产品暴露于高温和紫外线 (UV) 光下可以帮助饮料制造商减少或抑制其产品中苯的形成。[29][30][31]
除了生成苯外,英国谢菲尔德大学的彼得·派珀在研究苯甲酸钠对活酵母细胞的影响后,认为苯甲酸钠自身便会对细胞线粒体中的DNA造成破坏。由于粒线体是细胞呼吸的场所,因此对线粒体的损害会影响细胞的正常功能,在严重时可能导致细胞凋亡,从而加速机体的衰老,这个研究结果并没有得到英国食品标准局的肯定。[32][33][34][35][36]
此外在儿童中,超量摄入苯甲酸钠可能与哮喘、过敏或注意力缺陷多动障碍有关,并会影响人体认知功能与神经调(Piper, 2018)[37]过去也有研究认为碳酸饮料中的苯甲酸钠与其他人工色素共同食用可能会加剧儿童的多动症,但由于对苯甲酸钠的研究结论并不一致,因此这个研究结果并没有得到英国食品标准局的肯定。[38][39][40]
参见
参考资料
- ^ 1.0 1.1 1.2 1.3 1.4 sodium benzoate. chemister.ru. [2022-12-28]. (原始内容存档于2023-04-06).
- ^ 2.0 2.1 2.2 来源:Sigma-Aldrich Co., Sodium benzoate (2014-05-23查阅).
- ^ del Olmo, Ana; Calzada, Javier; Nuñez, Manuel. Benzoic acid and its derivatives as naturally occurring compounds in foods and as additives: Uses, exposure, and controversy. Critical Reviews in Food Science and Nutrition. 2015-11-20, 57 (14): 3084–3103. PMID 26587821. S2CID 205692543. doi:10.1080/10408398.2015.1087964.
- ^ International Programme on Chemical Safety. Inchem.org. [2022-02-09]. (原始内容存档于2021-12-25).
- ^ Sodium benzoate. PubChem. [2022-12-28]. (原始内容存档于2023-05-28). National Library of Medicine
- ^ Robitussin (Guaifenesin). Rxmed.com. [2013-01-14]. (原始内容存档于2015-09-24).
- ^ Code of Federal Regulations Title 21. www.accessdata.fda.gov. [2022-12-28]. (原始内容存档于2021-12-25).
- ^ AAFCO. Official Publication: 262. 2004.
- ^ Saltmarsh, Mike. Recent trends in the use of food additives in the United Kingdom. Journal of the Science of Food and Agriculture. 2015-03-15, 95 (4): 649–652. ISSN 1097-0010. PMID 24789520. doi:10.1002/jsfa.6715.
... the preservative used in the study, sodium benzoate, has been replaced by potassium sorbate in the majority of soft drinks.
- ^ Häberle, J; Boddaert, N; Burlina, A; Chakrapani, A; Dixon, M; Huemer, M; Karall, D; Martinelli, D; Crespo, PS; Santer, R; Servais, A; Valayannopoulos, V; Lindner, M; Rubio, V; Dionisi-Vici, C. Suggested guidelines for the diagnosis and management of urea cycle disorders. Orphanet Journal of Rare Diseases. 2012, 7: 32. PMC 3488504
. PMID 22642880. doi:10.1186/1750-1172-7-32.
- ^ Wilcken, B. Problems in the management of urea cycle disorders. Molecular Genetics and Metabolism. 2004,. 81 Suppl 1: S86–91. PMID 15050980. doi:10.1016/j.ymgme.2003.10.016.
- ^ Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor (页面存档备份,存于互联网档案馆) December 2013
- ^ Digest of Neurology and Psychiatry. Institute of Living. 16 April 2018 –通过Google Books.
- ^ Mental Health Research Institute Staff Publications, University of Michigan. Mental Health Research Institute
- ^ Cinnamon May Help Halt Parkinson's Disease Progression - News Releases - Rush University Medical Center. [2022-12-28]. (原始内容存档于2018-06-18).
- ^ PHENYLBUTYRATE, SODIUM BENZOATE. National Institute of Diabetes and Digestive and Kidney Diseases. 2012 [2022-12-28]. (原始内容存档于2018-09-01).
- ^ Yücel, A; Ozyalçin, S; Talu, GK; Yücel, EC; Erdine, S. Intravenous administration of caffeine sodium benzoate for postdural puncture headache. Reg Anesth Pain Med. 1999, 24 (1): 51–4. PMID 9952095. doi:10.1097/00115550-199924010-00010.
- ^ mayoclinic.org, Caffeine And Sodium Benzoate (Injection Route). [2022-12-28]. (原始内容存档于2021-12-25).
- ^ ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate. [2022-12-28]. (原始内容存档于2021-12-25).
- ^ Krebs H. A., Wiggins D., Stubbs M., Sols A., Bedoya F. Studies on the mechanism of the antifungal action of benzoate. Biochem. J. September 1983, 214 (3): 657–663. PMC 1152300
. PMID 6226283. doi:10.1042/bj2140657.
- ^ Bedford PG, Clarke EG. Experimental benzoic acid poisoning in the cat. Vet. Rec. January 1972, 90 (3): 53–8. PMID 4672555.
- ^ AFCO. Official Publication: 262. 2004.
- ^ Clague, J.A. & Fellers, C.R. Relation of benzoic acid content and other constituents of cranberries to keeping quality. Plant Physiology. 1934, (9): 631–6.
- ^ Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate. [2009-05-08]. (原始内容存档于2020-11-14).
- ^ Cosmetic Ingredient Review Expert Panel Bindu Nair. Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. Int J Tox. 2001, 20 (Suppl 3): 23–50.
- ^ FDA, 2006. "Data on Benzene in Soft Drinks and Other Beverages, " United States Food and Drug Administration. Accessed June 2nd at: 存档副本. [2008-03-26]. (原始内容存档于2008-03-26).
- ^ Sadighara, Parisa; Pirhadi, Mohadeseh; Sadighara, Melina; Shavaly-Gilani, Parisa; Zirak, Mohammad Reza; Zeinali, Tayebeh. Benzene food exposure and their prevent methods: a review. Nutrition & Food Science. 2022-01-01, 52 (6). ISSN 0034-6659. doi:10.1108/NFS-10-2021-0306.
- ^ The Daily Mail DNA Damage Fear (页面存档备份,存于互联网档案馆) 24 May 2008
- ^ Benzene as a Chemical Hazard in Processed Foods
- ^ Guidance Document to Mitigate the Potential for Benzene Formation in Beverages
- ^ Evaluation of accelerated UV and thermal testing for benzene formation in beverages containing benzoate and ascorbic acid. Journal of Food Science.
- ^ Martin Hickman Caution: Some soft drinks may seriously harm your health (页面存档备份,存于互联网档案馆) The Independent on Sunday 27 May 2007
- ^ Martin Hickman E211 Revealed: Evidence highlights new fear over drinks additive 互联网档案馆的存档,存档日期2008-07-06. The Independent on Sunday 27 May 2007
- ^ Leading article: Children deserve our doubts 互联网档案馆的存档,存档日期2007-12-12. The Independent on Sunday 27 May 2007
- ^ Chris Mercer Fresh health fears hit benzoate in soft drinks (页面存档备份,存于互联网档案馆) BeverageDaily 29 May 2007
- ^ Piper PW. Yeast superoxide dismutase mutants reveal a pro-oxidant action of weak organic acid food preservatives. Free Radic. Biol. Med. December 1999, 27 (11-12): 1219–27 [2009-05-08]. PMID 10641714. (原始内容存档于2018-09-04).
- ^ Piper, Peter W. Potential Safety Issues Surrounding the Use of Benzoate Preservatives. Beverages. 2018-06, 4 (2) [2022-10-24]. ISSN 2306-5710. doi:10.3390/beverages4020033. (原始内容存档于2022-10-25) (英语).
- ^ Food Standards Agency issues revised advice on certain artificial colours (页面存档备份,存于互联网档案馆) 6 September 2007
- ^ Food Colorings and Hyperactivity (页面存档备份,存于互联网档案馆) "Myomancy" 7 September 2007
- ^ Agency revises advice on certain artificial colours (页面存档备份,存于互联网档案馆) Food Standards Agency 11 September 2007
延伸阅读
- Kubota K, Ishizaki T. Dose-dependent pharmacokinetics of benzoic acid following oral administration of sodium benzoate to humans. Eur. J. Clin. Pharmacol. 1991, 41 (4): 363–8. PMID 1804654.
Although the maximum rate of biotransformation of benzoic acid to hippuric acid varied between 17.2 and 28.8 mg.kg-1.h-1 among the six individuals, the mean value (23.0 mg.kg-1.h-1) was fairly close to that provided by daily maximum dose (0.5 g.kg-1.day-1) recommended in the treatment of hyperammonaemia in patients with inborn errors of ureagenesis
- Andersen A. Final report on the safety assessment of benzaldehyde. Int. J. Toxicol. 2006, 25 (Suppl 1): 11–27. PMID 16835129. doi:10.1080/10915810600716612.
外部链接
- 国际化学品安全署对苯甲酸和苯甲酸盐毒性的报告 (页面存档备份,存于互联网档案馆) (英文)
- 苯甲酸钠与儿童多动症的关系 (页面存档备份,存于互联网档案馆)——TIME杂志新闻
- 苯甲酸钠转化为苯的机理(幻灯片文件)(英文)
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