酚酞

酚酞
	IUPAC名; 3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-one; 3,3-雙(4-羥基苯基)-2-(3H)-苯並呋喃酮
識別
CAS號	77-09-8
PubChem	4764
SMILES	O=C1OC(c2ccccc12)(c3ccc(O)cc3)c4ccc(O)cc4;
DrugBank	DB04824
KEGG	D05456
性質
化學式	C20H14O4
摩爾質量	318.323 g·mol⁻¹
密度	1.277 g cm−3, 32 ℃
熔點	258℃~263℃（）
溶解性（水）	400mg/L
溶解性（其他溶劑）	不溶於苯，易溶於乙醇和醚，微溶於DMSO
λmax	552 nm (1st); 374 nm (2nd) nm
危險性
	歐盟危險性符號; 有害 Xn
警示術語	R：R22, R40, R45, R62, R68,
安全術語	S：S53, S45
	GHS危險性符號;
GHS提示詞	danger
H-術語	H341, H350, H361
P-術語	P201, P281, P308+313
NFPA 704	3 2 0
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

酚酞（英語：Phenolphthalein）是一種化合物，分子式為C₂₀H₁₄O₄，通常以簡寫形式寫成「PP」、「HIn」、「HPh」、「phph」或簡稱為「Ph」。酚酞通常用作酸鹼指示劑。酚酞在酸性溶液中變為無色，在鹼性溶液中變為粉紅色。

酚酞微溶於水，通常溶解在醇中以用於實驗。它是一種弱酸，可在溶液中失去H⁺離子。酚酞分子是無色的，失去質子的酚酞離子是紫紅色的。其在較高pH中會進一步失去質子並導致褪色。濃硫酸中的酚酞離子是由於磺化引起的橙紅色。^[2]

用途[編輯]

酸鹼指示劑[編輯]

酚酞（酸鹼指示劑）
低於pH 8.3 時		高於pH 10.0 時
8.3	⇌	10.0

酚酞的常見用途是作為酸鹼指示劑。其與甲基紅、溴百里酚藍和百里酚藍一起作為通用指示劑的成分。^[3]

酚酞在水溶液中根據溶液的pH產生不同的形式。^[2]^[4]^[5]^[6]

文獻中關於化合物的水合形式和硫酸中的顏色存在不一致。Wittke在1983年報告稱，在強酸性條件下，其以質子化形式（HIn⁺）存在而呈現橙色。然而後來的論文表明，這種顏色是由於其被磺化為酚磺酞。^[2]

在強酸性和弱鹼性條件之間，內酯形式（HIn）是無色的。雙去質子化（In^2-）酚鹽形式（苯酚的陰離子形式）產生熟悉的粉紅色。在強鹼性溶液中，酚酞轉化為In(OH)^3-形式，其粉紅色會經歷相當緩慢的褪色反應^[6]，當pH值大於13時變為完全無色。酚酞的pK_A值為9.05、9.50 和12，而酚磺酞的pK_A值為1.2和7.70。^[2]

	H₃In⁺	H₂In	In²⁻	In(OH)³⁻
結構
球棍模型
pH	<-1 在H₂SO₄中^[4]	0−8.3	8.3−10.0^[7]	>12
條件	強酸性	酸性、近中性	鹼性	強鹼性
顏色	橙色	無色	粉紅色至品紅色	無色
圖片


酚酞結構隨pH值的變化動畫: H₃In⁺ → H₂In → In²⁻ → In(OH)³⁻

醫療用途[編輯]

酚酞作為瀉藥已被使用了一個多世紀，但由於擔憂其致癌性^[8]^[9]，現已從多數國家的非處方藥列表中移除。^[10]

儘管有對其致癌性的擔憂，但使用酚酞作為瀉藥不太可能導致卵巢癌。^[11]

酚酞已被添加到歐洲化學品管理局的高度關注物質 (SVHC) 候選清單中。^[12]

合成[編輯]

酚酞是通過鄰苯二甲酸酐與兩份苯酚在濃硫酸加熱的情況下縮合製得的。這個方法由阿道夫·馮·拜爾於1871年發現。^[13]^[14]^[15]

該反應也可以由氯化鋅和氯化亞碸的混合物催化。^[17]

參見[編輯]

參考資料[編輯]

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Phenolphthalein. [2014-10-07]. （原始內容存檔於2015-11-08）.
^ ^2.0 ^2.1 ^2.2 ^2.3 Tamura, Zenzo. Spectrophotometric Analysis of the Relationship between Dissociation and Coloration, and of the Structural Formulas of Phenolphthalein in Aqueous Solution. Analytical Sciences. December 1996, 12 (6): 927–930. doi:10.2116/analsci.12.927.
^ Universal Indicator. ISCID Encyclopedia of Science and Philosophy. （原始內容存檔於September 25, 2006）.
^ ^4.0 ^4.1 Wittke, Georg. Reactions of phenolphthalein at various pH values. Journal of Chemical Education. 1 March 1983, 60 (3): 239. Bibcode:1983JChEd..60..239W. ISSN 0021-9584. doi:10.1021/ed060p239.
^ Abdel-Hamid, Refat. The Adsorption Behavior of Phenolphthalein at a Mercury Electrode in Water-Ethanol Solutions. Monatshefte für Chemie - Chemical Monthly. 1 September 1998, 129 (8): 817–826. S2CID 92339258. doi:10.1007/PL00013491.
^ ^6.0 ^6.1 Kunimoto, Ko-Ki. Molecular structure and vibrational spectra of phenolphthalein and its dianion. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (SAA). February 2001, 57 (2): 265–271. Bibcode:2001AcSpA..57..265K. PMID 11206560. doi:10.1016/S1386-1425(00)00371-1.
^ Rathod, Balraj B.; Murthy, Sahana; Bandyopadhyay, Subhajit. Is this Solution Pink Enough? A Smartphone Tutor to Resolve the Eternal Question in Phenolphthalein-Based Titration. Journal of Chemical Education. 20 February 2019, 96 (3): 486–494. Bibcode:2019JChEd..96..486R. S2CID 104475433. doi:10.1021/acs.jchemed.8b00708.
^ Dunnick, J. K.; Hailey, J. R. Phenolphthalein Exposure Causes Multiple Carcinogenic Effects in Experimental Model Systems (PDF). Cancer Research. 1996, 56 (21): 4922–4926 [2022-02-22]. PMID 8895745. （原始內容存檔 (PDF)於2022-02-17）.
^ Tice, R. R.; Furedi-Machacek, M.; Satterfield, D.; Udumudi, A.; Vasquez, M.; Dunnick, J. K. Measurement of Micronucleated Erythrocytes and DNA Damage during Chronic Ingestion of Phenolphthalein in Transgenic Female Mice Heterozygous for the p53 Gene. Environmental and Molecular Mutagenesis. 1998, 31 (2): 113–124. PMID 9544189. doi:10.1002/(SICI)1098-2280(1998)31:2<113::AID-EM3>3.0.CO;2-N.
^ Spiller, H. A.; Winter, M. L.; Weber, J. A.; Krenzelok, E. P.; Anderson, D. L.; Ryan, M. L. Skin Breakdown and Blisters from Senna-Containing Laxatives in Young Children. The Annals of Pharmacotherapy. May 2003, 37 (5): 636–639. PMID 12708936. S2CID 31837142. doi:10.1345/aph.1C439.
^ Cooper, G. S.; Longnecker, M. P.; Peters, R. K. Ovarian Cancer Risk and Use of Phenolphthalein-Containing Laxatives. Pharmacoepidemiology and Drug Safety. 2004, 13 (1): 35–39 [2019-06-26]. PMID 14971121. S2CID 24783082. doi:10.1002/pds.824. （原始內容存檔於2022-01-26）.
^ Phenolphthalein - Substance Information - ECHA. echa.europa.eu. [2017-11-06]. （原始內容存檔於2018-06-12）（英國英語）.
^ Baeyer, A. Ueber eine neue Klasse von Farbstoffen. Berichte der Deutschen Chemischen Gesellschaft. 1871, 4 (2): 555–558 [2020-09-02]. doi:10.1002/cber.18710040209. （原始內容存檔於2021-02-14）.
^ Baeyer, A. Ueber die Phenolfarbstoffe. Berichte der Deutschen Chemischen Gesellschaft. 1871, 4 (2): 658–665 [2019-06-26]. doi:10.1002/cber.18710040247. （原始內容存檔於2021-10-11）.
^ Baeyer, A. Ueber die Phenolfarbstoffe. Polytechnisches Journal. 1871, 201 (89): 358–362 [2022-02-22]. （原始內容存檔於2021-10-11）.
^ Max Hubacher, 美國專利第2,192,485號 (1940 to Ex Lax Inc)
^ 美國專利第2,522,939號

[sigma-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Phenolphthalein. [2014-10-07]. （原始內容存檔於2015-11-08）.

[Tamura1996-2] 2.0 ^2.1 ^2.2 ^2.3 Tamura, Zenzo. Spectrophotometric Analysis of the Relationship between Dissociation and Coloration, and of the Structural Formulas of Phenolphthalein in Aqueous Solution. Analytical Sciences. December 1996, 12 (6): 927–930. doi:10.2116/analsci.12.927.

[3] Universal Indicator. ISCID Encyclopedia of Science and Philosophy. （原始內容存檔於September 25, 2006）.

[wittke1983-4] 4.0 ^4.1 Wittke, Georg. Reactions of phenolphthalein at various pH values. Journal of Chemical Education. 1 March 1983, 60 (3): 239. Bibcode:1983JChEd..60..239W. ISSN 0021-9584. doi:10.1021/ed060p239.

[Abdel-Hamid-5] Abdel-Hamid, Refat. The Adsorption Behavior of Phenolphthalein at a Mercury Electrode in Water-Ethanol Solutions. Monatshefte für Chemie - Chemical Monthly. 1 September 1998, 129 (8): 817–826. S2CID 92339258. doi:10.1007/PL00013491.

[Kunimoto2001-6] 6.0 ^6.1 Kunimoto, Ko-Ki. Molecular structure and vibrational spectra of phenolphthalein and its dianion. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (SAA). February 2001, 57 (2): 265–271. Bibcode:2001AcSpA..57..265K. PMID 11206560. doi:10.1016/S1386-1425(00)00371-1.

[7] Rathod, Balraj B.; Murthy, Sahana; Bandyopadhyay, Subhajit. Is this Solution Pink Enough? A Smartphone Tutor to Resolve the Eternal Question in Phenolphthalein-Based Titration. Journal of Chemical Education. 20 February 2019, 96 (3): 486–494. Bibcode:2019JChEd..96..486R. S2CID 104475433. doi:10.1021/acs.jchemed.8b00708.

[8] Dunnick, J. K.; Hailey, J. R. Phenolphthalein Exposure Causes Multiple Carcinogenic Effects in Experimental Model Systems (PDF). Cancer Research. 1996, 56 (21): 4922–4926 [2022-02-22]. PMID 8895745. （原始內容存檔 (PDF)於2022-02-17）.

[9] Tice, R. R.; Furedi-Machacek, M.; Satterfield, D.; Udumudi, A.; Vasquez, M.; Dunnick, J. K. Measurement of Micronucleated Erythrocytes and DNA Damage during Chronic Ingestion of Phenolphthalein in Transgenic Female Mice Heterozygous for the p53 Gene. Environmental and Molecular Mutagenesis. 1998, 31 (2): 113–124. PMID 9544189. doi:10.1002/(SICI)1098-2280(1998)31:2<113::AID-EM3>3.0.CO;2-N.

[10] Spiller, H. A.; Winter, M. L.; Weber, J. A.; Krenzelok, E. P.; Anderson, D. L.; Ryan, M. L. Skin Breakdown and Blisters from Senna-Containing Laxatives in Young Children. The Annals of Pharmacotherapy. May 2003, 37 (5): 636–639. PMID 12708936. S2CID 31837142. doi:10.1345/aph.1C439.

[11] Cooper, G. S.; Longnecker, M. P.; Peters, R. K. Ovarian Cancer Risk and Use of Phenolphthalein-Containing Laxatives. Pharmacoepidemiology and Drug Safety. 2004, 13 (1): 35–39 [2019-06-26]. PMID 14971121. S2CID 24783082. doi:10.1002/pds.824. （原始內容存檔於2022-01-26）.

[12] Phenolphthalein - Substance Information - ECHA. echa.europa.eu. [2017-11-06]. （原始內容存檔於2018-06-12）（英國英語）.

[13] Baeyer, A. Ueber eine neue Klasse von Farbstoffen. Berichte der Deutschen Chemischen Gesellschaft. 1871, 4 (2): 555–558 [2020-09-02]. doi:10.1002/cber.18710040209. （原始內容存檔於2021-02-14）.

[14] Baeyer, A. Ueber die Phenolfarbstoffe. Berichte der Deutschen Chemischen Gesellschaft. 1871, 4 (2): 658–665 [2019-06-26]. doi:10.1002/cber.18710040247. （原始內容存檔於2021-10-11）.

[15] Baeyer, A. Ueber die Phenolfarbstoffe. Polytechnisches Journal. 1871, 201 (89): 358–362 [2022-02-22]. （原始內容存檔於2021-10-11）.

[16] Max Hubacher, 美國專利第2,192,485號 (1940 to Ex Lax Inc)

[17] 美國專利第2,522,939號

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