苯甲酸鈉
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苯甲酸鈉 | |
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IUPAC名 Sodium benzoate | |
別名 | E211、苯酸鈉、安息香酸鈉、苯甲酸鈉鹽 |
識別 | |
CAS號 | 532-32-1 ![]() |
PubChem | 517055 |
ChemSpider | 10305 |
SMILES |
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InChI |
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InChIKey | WXMKPNITSTVMEF-REWHXWOFAY |
ChEBI | 113455 |
RTECS | DH6650000 |
性質 | |
化學式 | C7H5NaO2 |
摩爾質量 | 144.1 g·mol−1 |
外觀 | 白色或無色結晶粉末 |
氣味 | 無味 |
密度 | 1.497 g/cm3 |
熔點 | 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 | 溶於液氨、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-戴奧辛) | 0.818 mg/kg(25 °C)[1] |
藥理學 | |
ATC代碼 | A16AX11(A16) |
危險性 | |
GHS危險性符號![]() | |
GHS提示詞 | Warning |
H-術語 | H319[2] |
P-術語 | P305+351+338[2] |
NFPA 704 | |
致死量或濃度: | |
LD50(中位劑量)
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4100 mg/kg(大鼠,口服) |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
苯甲酸鈉是苯甲酸的鈉鹽,化學式為C
6H
5CO
2Na,是一種白色結晶固體。苯甲酸鈉是很常用的食品防腐劑,E編碼為E211。
自然產生
許多植物是苯甲酸及其鹽和酯的天然來源,尤其是蔓越莓和覆盆子等漿果。[3]
生產
用途
防腐劑
苯甲酸鈉可用作防腐劑。它最廣泛用於酸性食品,如沙拉醬、碳酸飲料、果醬和果汁、泡菜、調味料和霜凍優格。在藥品和化妝品中也用作防腐劑。[5][6]在酸性條件下能轉化為苯甲酸,具有抑菌作用。苯甲酸水溶性差,一般不直接使用。美國FDA將其作為食品防腐劑的濃度限制為0.1%(按重量計)。[7]根據美國飼料控制官員協會的規定,苯甲酸鈉也被允許用作動物食品添加劑,最高含量為0.1%。[8]在英國,大多數軟飲料中的苯甲酸鈉已被山梨酸鉀取代。[9]
藥物
苯甲酸鈉因其結合胺基酸的能力而被用作尿素循環障礙的治療藥物。[10][11]最近的研究表明,苯甲酸鈉作為附加療法(1g/天)可能對精神分裂症有益。[12][13][14]
苯甲酸鈉與咖啡因一起用於治療硬膜穿刺後頭痛、與吸毒過量導致的呼吸抑制,[17][18]並與麥角胺一起治療血管性頭痛。[19]
機制
苯甲酸鈉的防腐機制為:苯甲酸親油性較強,容易穿過細胞膜進入細胞內,干擾細菌和黴菌等微生物細胞膜的通透性,抑制細胞膜對氨基酸的吸收。進入細胞內的苯甲酸分子抑制微生物細胞呼吸酶系的活性,使無氧呼吸中磷酸果糖激酶催化的反應速率下降95%,從而起到防腐作用。[20]
對健康的影響
苯甲酸/苯甲酸鹽天然存在於藍莓、蔓越莓、梅乾、肉桂和丁香[哪個/哪些?]中。少量的苯甲酸鈉對人體無毒害,它可以在體內很快被吸收,主要與甘氨酸結合以馬尿酸的形式排出體外,也有一小部分與葡糖醛酸結合為1-苯甲酰葡糖醛酸而排出。10-14小時便可從體內全部排出,因此少量的苯甲酸鈉不會有積蓄作用。但是貓對苯甲酸比較敏感,過量攝取容易出現興奮、神經過敏、失去聽力和平衡等徵狀,因此在製造寵物食品時需注意,但少量攝取並不影響健康。[21][22]
FDA規定食品中的苯甲酸鈉含量不得超過0.1%(以重量計)。[23]國際化學品安全署的研究發現每天攝入647-835mg每千克體重的苯甲酸鈉不會對健康產生負面影響。[24][25]
苯甲酸鹽類防腐劑(苯甲酸鈉、苯甲酸鉀)可以與維生素C反應生成具有致癌性的苯,[26]尤其在柑橘類飲料中更容易存在,(Sadighara et al., 2022)[27]。由於各國對於飲料中苯的含量標準不一,不同的飲料中苯的含量也不相同,而且上述分解反應也與光照、加熱和儲存時間等諸多因素有很大關係,因此目前對苯甲酸鹽產生的苯是否超標沒有定論。這使得公眾對苯甲酸鹽毒性的質疑持續不斷。可口可樂公司因此宣布將在其產品中逐漸禁止苯甲酸鈉的使用,而用更加天然的防腐劑代替。[28]但用另一種抗氧化劑代替抗壞血酸,添加 EDTA 或聚磷酸鈉以螯合催化羥基自由基形成的金屬離子,並審查儲存條件和保質期以儘量減少產品暴露於高溫和紫外線 (UV) 光下可以幫助飲料製造商減少或抑制其產品中苯的形成。[29][30][31]
除了生成苯外,英國謝菲爾德大學的彼得·派珀在研究苯甲酸鈉對活酵母細胞的影響後,認為苯甲酸鈉自身便會對細胞線粒體中的DNA造成破壞。由於粒線體是細胞呼吸的場所,因此對線粒體的損害會影響細胞的正常功能,在嚴重時可能導致細胞凋亡,從而加速機體的衰老,這個研究結果並沒有得到英國食品標準局的肯定。[32][33][34][35][36]
此外在兒童中,超量攝入苯甲酸鈉可能與哮喘、過敏或注意力缺陷多動障礙有關,並會影響人體認知功能與神經調(Piper, 2018)[37]過去也有研究認為碳酸飲料中的苯甲酸鈉與其他人工色素共同食用可能會加劇兒童的多動症,但由於對苯甲酸鈉的研究結論並不一致,因此這個研究結果並沒有得到英國食品標準局的肯定。[38][39][40]
參見
參考資料
- ^ 1.0 1.1 1.2 1.3 1.4 sodium benzoate. chemister.ru. [2022-12-28]. (原始內容存檔於2023-04-06).
- ^ 2.0 2.1 2.2 來源:Sigma-Aldrich Co., Sodium benzoate (2014-05-23查閱).
- ^ 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]. (原始內容存檔於2021-12-25).
- ^ Sodium benzoate. PubChem. [2022-12-28]. (原始內容存檔於2023-05-28). National Library of Medicine
- ^ Robitussin (Guaifenesin). Rxmed.com. [2013-01-14]. (原始內容存檔於2015-09-24).
- ^ Code of Federal Regulations Title 21. www.accessdata.fda.gov. [2022-12-28]. (原始內容存檔於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 (頁面存檔備份,存於網際網路檔案館) December 2013
- ^ Digest of Neurology and Psychiatry. Institute of Living. 16 April 2018 –透過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]. (原始內容存檔於2018-06-18).
- ^ PHENYLBUTYRATE, SODIUM BENZOATE. National Institute of Diabetes and Digestive and Kidney Diseases. 2012 [2022-12-28]. (原始內容存檔於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]. (原始內容存檔於2021-12-25).
- ^ ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate. [2022-12-28]. (原始內容存檔於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]. (原始內容存檔於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]. (原始內容存檔於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 (頁面存檔備份,存於網際網路檔案館) 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 (頁面存檔備份,存於網際網路檔案館) The Independent on Sunday 27 May 2007
- ^ Martin Hickman E211 Revealed: Evidence highlights new fear over drinks additive 網際網路檔案館的存檔,存檔日期2008-07-06. The Independent on Sunday 27 May 2007
- ^ Leading article: Children deserve our doubts 網際網路檔案館的存檔,存檔日期2007-12-12. The Independent on Sunday 27 May 2007
- ^ Chris Mercer Fresh health fears hit benzoate in soft drinks (頁面存檔備份,存於網際網路檔案館) 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. (原始內容存檔於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. (原始內容存檔於2022-10-25) (英語).
- ^ Food Standards Agency issues revised advice on certain artificial colours (頁面存檔備份,存於網際網路檔案館) 6 September 2007
- ^ Food Colorings and Hyperactivity (頁面存檔備份,存於網際網路檔案館) "Myomancy" 7 September 2007
- ^ Agency revises advice on certain artificial colours (頁面存檔備份,存於網際網路檔案館) Food Standards Agency 11 September 2007
延伸閱讀
- 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.
外部連結
- 國際化學品安全署對苯甲酸和苯甲酸鹽毒性的報告 (頁面存檔備份,存於網際網路檔案館) (英文)
- 苯甲酸鈉與兒童多動症的關係 (頁面存檔備份,存於網際網路檔案館)——TIME雜誌新聞
- 苯甲酸鈉轉化為苯的機理(幻燈片文件)(英文)
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