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
识别
CAS号	77-09-8
PubChem	4764
SMILES	O=C1OC(c2ccccc12)(c3ccc(O)cc3)c4ccc(O)cc4;
DrugBank	DB04824
KEGG	D05456
性质
化学式	C20H14O4
摩尔质量	318.323 g·mol⁻¹
密度	1.277 g cm−3, 32 ℃
熔点	258℃~263℃（）
溶解性（水）	400mg/L
溶解性（其他溶剂）	不溶于苯，易溶于乙醇和醚，微溶于DMSO
λmax	552 nm (1st); 374 nm (2nd) nm
危险性
	欧盟危险性符号; 有害 Xn
警示术语	R：R22, R40, R45, R62, R68,
安全术语	S：S53, S45
	GHS危险性符号;
GHS提示词	danger
H-术语	H341, H350, H361
P-术语	P201, P281, P308+313
NFPA 704	3 2 0
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

酚酞（英語：phenolphthalein）是一種化合物，分子式為C₂₀H₁₄O₄，常用“PP”、“HIn”、“HPh”、“phph”或“Ph”为速记符号。酚酞通常用作酸鹼指示劑，也曾作为刺激性泻剂。酚酞在酸性溶液中变为无色，在碱性溶液中变为粉红色，属于酞类染料（phthalein dyes）。

酚酞微溶于水，通常溶解在醇中以用于实验。它是一种弱酸，可在溶液中失去H⁺离子。酚酞分子是无色的，失去质子的酚酞离子是紫红色的。其在较高pH中会进一步失去质子并导致褪色。浓硫酸中的酚酞离子是由于磺化引起的橙红色。^[2]

用途

酸碱指示剂

酚酞（酸碱指示剂）
低於pH 8.3 时		高於pH 10.0 时
8.3	⇌	10.0

酚酞的常见用途是作为酸碱指示剂。其与甲基红、溴百里酚蓝和百里酚蓝一起作为通用指示剂的成分。^[3]

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

文献中关于化合物的水合形式和硫酸中的颜色存在不一致。Wittke在1983年报告称，在强酸性条件下，其以质子化形式（HIn⁺）存在而呈现橙色。然而后来的论文表明，这种颜色是由于其被磺化为酚磺酞。^[2]

在强酸性和弱碱性条件之间，内酯形式（HIn）是无色的。双去质子化（In^2-）酚盐形式（苯酚的阴离子形式）產生熟悉的粉红色。在强碱性溶液中，酚酞转化为In(OH)^3-形式，其粉红色会经历相当缓慢的褪色反应^[6]，当pH值大于13时变为完全无色。酚酞的pK_A值为9.05、9.50 和12，而酚磺酞的pK_A值为1.2和7.70。^[2]

	H₃In⁺	H₂In	In²⁻	In(OH)³⁻
结构
球棍模型
pH	<-1 在H₂SO₄中^[4]	0−8.3	8.3−10.0^[7]	>12
条件	强酸性	酸性、近中性	碱性	强碱性
颜色	橙色	无色	粉红色至品红色	无色
图片


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

医疗用途

酚酞作为泻药已被使用了一个多世纪，但由于擔憂其致癌性^[8]^[9]，现已从多数国家的非处方药列表中移除。^[10]

尽管有對其致癌性的擔憂，但使用酚酞作为泻药不太可能导致卵巢癌。^[11]

酚酞已被添加到欧洲化学品管理局的高度关注物质 (SVHC) 候选清单中。^[12]

合成

酚酞是通过邻苯二甲酸酐与两份苯酚在浓硫酸加热的情况下缩合制得的。这个方法由阿道夫·冯·拜尔于1871年发现。^[13]^[14]^[15]

该反应也可以由氯化锌和氯化亚砜的混合物催化。^[17]

參見

参考资料

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Phenolphthalein. [2014-10-07]. （原始内容存档于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. （原始内容存档于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. （原始内容存档 (PDF)于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. （原始内容存档于2022-01-26）.
^ Phenolphthalein - Substance Information - ECHA. echa.europa.eu. [2017-11-06]. （原始内容存档于2018-06-12）（英国英语）.
^ 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. （原始内容存档于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. （原始内容存档于2021-10-11）.
^ Baeyer, A. Ueber die Phenolfarbstoffe. Polytechnisches Journal. 1871, 201 (89): 358–362 [2022-02-22]. （原始内容存档于2021-10-11）.
^ Max Hubacher, 美國專利第2,192,485号 (1940 to Ex Lax Inc)
^ 美國專利第2,522,939号

[sigma-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Phenolphthalein. [2014-10-07]. （原始内容存档于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. （原始内容存档于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. （原始内容存档 (PDF)于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. （原始内容存档于2022-01-26）.

[12] Phenolphthalein - Substance Information - ECHA. echa.europa.eu. [2017-11-06]. （原始内容存档于2018-06-12）（英国英语）.

[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. （原始内容存档于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. （原始内容存档于2021-10-11）.

[15] Baeyer, A. Ueber die Phenolfarbstoffe. Polytechnisches Journal. 1871, 201 (89): 358–362 [2022-02-22]. （原始内容存档于2021-10-11）.

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

[17] 美國專利第2,522,939号

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