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Phenol red (also known as phenolsulfonphthalein or PSP) is a pH indicator frequently used in cell biology laboratories.

Chemical structure and properties

Phenol red exists as a red crystal that is stable in air. Its solubility is 0.77 grams per liter (g/l) in water and 2.9 g/l in ethanol.^[1] It is a weak acid with pK_a = 8.00 at 20 °C (68 °F).

A solution of phenol red is used as a pH indicator: its color exhibits a gradual transition from yellow to red over the pH range 6.8 to 8.2. Above pH 8.2, phenol red turns a bright pink (fuchsia) color.^[2]^[3]

Phenol red (pH indicator)
below pH 6.8		above pH 8.2
6.8	⇌	8.2

This solution contains a pH indicator which helps in monitoring of the pH changes in the cell culture. It will change from red to yellow when the pH value decreases.

In crystalline form, and in solution under very acidic conditions (low pH), the compound exists as a zwitterion as in the structure shown above, with the sulfate group negatively charged, and the ketone group carrying an additional proton. This form is sometimes symbolically written as H₂⁺PS⁻ and is orange-red. If the pH is increased (pK_a = 1.2), the proton from the ketone group is lost, resulting in the yellow, negatively charged ion denoted as HPS⁻. At still higher pH (pK_a = 7.7), the phenol's hydroxide group loses its proton, resulting in the red ion denoted as PS²⁻.^[4]

In several sources, the structure of phenol red is shown with the sulfur atom being part of a cyclic group, similar to the structure of phenolphthalein.^[1]^[5] However, this cyclic structure could not be confirmed by X-ray crystallography.^[6]

Several indicators share a similar structure to phenol red, including bromothymol blue, thymol blue, bromocresol purple, thymolphthalein, and phenolphthalein. (A table of other common chemical indicators is available in the article on pH indicators.)

Phenolsulfonphthalein test

Phenol red was used in the phenolsulfonphthalein test to estimate the overall blood flow through the kidney and is now obsolete.

The test is based on the fact that phenol red is excreted almost entirely in the urine. Phenol red solution is administered intravenously, the urine produced is collected. By measuring the amount of phenol red excreted colorimetrically, kidney function can be determined.^[7]

Indicator for cell cultures

Phenol red, 40 µM: colors in cell culture medium at a pH range from 6.0 to 8.0.

Most living tissues prosper at a near-neutral pH; that is, a pH close to 7. The pH of blood ranges from 7.35 to 7.45, for instance. When cells are grown in tissue culture, the medium in which they grow is held close to this physiological pH. A small amount of phenol red added to this growth medium will have a pink-red color under normal conditions. Typically, 15 mg /l are used for cell culture.

In the event of problems, waste products produced by dying cells or overgrowth of contaminants will cause a change in pH, leading to a change in indicator color. For example, a culture of relatively slowly dividing mammalian cells can be quickly overgrown by bacterial contamination. This usually results in an acidification of the medium, turning it yellow. Many biologists find this a convenient way to rapidly check on the health of tissue cultures. In addition, the waste products produced by the mammalian cells themselves will slowly decrease the pH, gradually turning the solution orange and then yellow. This color change is an indication that even in the absence of contamination, the medium needs to be replaced (generally, this should be done before the medium has turned completely orange).

Since the color of phenol red can interfere with some spectrophotometric and fluorescent assays, many types of tissue culture media are also available without phenol red.

Estrogen mimic

Phenol red is a weak estrogen mimic, and in cell cultures can enhance the growth of cells that express the estrogen receptor.^[8]

An important breakthrough in biotechnology was reported in 2005 by Bukovsky and coworkers. Using phenol red as a differentiation factor, they produced human oocytes (eggs) from cells scraped from the surface of adult ovaries. These cells on the outer ovarian surface are known as ovarian surface epithelial cells. Such cells had been taken from five women aged 39 to 52 and were cultured in the presence of phenol red, inducing oogenesis.^[9]

Previously, human eggs had only been produced in vitro from totipotent, blastomeric embryonic stem cells. This experiment demonstrated viable human egg cells can easily be produced from an adult cell that already has some degree of specialization. Furthermore, it lessens the implications associated with the fact that women are born with all of the egg cells they will ever have throughout their lives. While this breakthrough was not without controversy, it provides hope for infertile women wishing to undergo in vitro fertilization, and hints at the possibility of new options for postmenopausal women, as well. It also suggests the future of stem cell research may not have to rely as heavily on human embryos as a source of unspecialized, totipotent cells for research.^{[citation needed]}

Use in swimming pool test kits

Phenol red, sometimes labelled with a different name, such as "Guardex Solution #2", is used as a pH indicator in home swimming pool test kits.^[10]

Chlorine can result in the bleaching of the dye in the absence of thiosulfate to inhibit the oxidizing chlorine. High levels of bromine can convert phenol red to bromophenol red (dibromophenolsulfonephthalein, whose lowered pK_a results in an indicator with a range shifted in the acidic direction - water at pH 6.8 will appear to test at 7.5). Even higher levels of bromine (>20 ppm) can result in the secondary conversion of bromophenol red to bromophenol blue with an even lower pK_a, erroneously giving the impression that the water has an extremely high pH despite being dangerously low.^[11]

References

^ ^a ^b Merck Index, 11th ed., 7213 Phenolsulfonphtalein
^ Merck Index, 13th ed., 7329 Phenolsulfonphthalein
^ Beilstein 5-19-03-00457
^ Tamura, Z.; Maeda M. (1997). "Differences between phthaleins and sulfonphthaleins". Yakugaku Zasshi (in Japanese) 117 (10–11): 764–770. PMID 9414589.
^ "Phenolsulfonphthalein". PubChem. NIH.
^ Yamaguchi, K.; Tamura, Z.; Maeda, M. (1997). "Molecular Structure of the Zwitterionic Form of Phenolsulfonphthalein" (pdf). Analytical Sciences 13 (3): 521–522. doi:10.2116/analsci.13.521.
^ "Phenolsulfonphthalein Test". Encyclopædia Britannica.
^ Berthois, Y.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. (1986). "Phenol red in tissue culture media is a weak estrogen: Implications concerning the study of estrogen-responsive cells in culture" (pdf). Proceedings of the National Academy of Sciences of the United States of America 83 (8): 2496–2500. doi:10.1073/pnas.83.8.2496. PMC 323325. PMID 3458212.
^ Bukovsky, A.; Svetlikova, M.; Caudle, M. R. (2005). "Oogenesis in Cultures Derived from Adult Human Ovaries" (pdf). Reproductive Biology and Endocrinology 3 (5): 17. doi:10.1186/1477-7827-3-17. PMC 1131924. PMID 15871747.
^ Guardex Solution 2 - Phenol Red Material Safety Data Sheet
^ Effect of Bromine on Phenol Red in pH Tests

External links

Video of phenol red activity demonstration and medium preparation

UpToDate Contents

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Effects of poloxamer 407-induced hyperlipidemia on hepatic multidrug resistance protein 2 (Mrp2/Abcc2) and the pharmacokinetics of mycophenolic acid in rats.

Kwon MH1, Yoon JN1, Baek YJ1, Kim YC2, Cho YY1, Kang HE3.
Biopharmaceutics & drug disposition.Biopharm Drug Dispos.2016 Sep;37(6):352-65. doi: 10.1002/bdd.2017.
Hepatic multidrug resistance-associated protein 2 (Mrp2) is responsible for the majority of the biliary elimination of endogenous and exogenous substances, therefore it is important to evaluate possible functional changes in Mrp2 activity under conditions of hyperlipidemia (HL). Thus, the present st
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Precision-cut human kidney slices as a model to elucidate the process of renal fibrosis.

Stribos EG1, Luangmonkong T2, Leliveld AM3, de Jong IJ3, van Son WJ4, Hillebrands JL5, Seelen MA4, van Goor H5, Olinga P6, Mutsaers HA7.
Translational research : the journal of laboratory and clinical medicine.Transl Res.2016 Apr;170:8-16.e1. doi: 10.1016/j.trsl.2015.11.007. Epub 2015 Nov 25.
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Wide-field medium-repetition-rate multiphoton microscopy reduces photodamage of living cells.

Macias-Romero C1, Zubkovs V2, Wang S1, Roke S1.
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Japanese Journal

Novel Diagnostic Method of Peritoneal Injury Using Dual Macromolecular Markers

Hirata Haruna,Miyamoto Hirotaka,Shimokawa Kenta,Nakashima Mikiro,Nakayama Morio,Fumoto Shintaro,Nishida Koyo
Biological and Pharmaceutical Bulletin 37(2), 262-267, 2014-02-01
… Then, marker substances of various molecular weights (phenolsulfonphthalein, fluorescein isothiocyanate-dextran (FD)-10, FD-40, FD-70, FD-2000 or tetramethylrhodamine-dextran (RD)-10) were injected into the peritoneal cavity. …
NAID 120005438841

Novel Diagnostic Method of Peritoneal Injury Using Dual Macromolecular Markers

Hirata Haruna,Miyamoto Hirotaka,Shimokawa Kenta,Nakashima Mikiro,Nakayama Morio,Fumoto Shintaro,Nishida Koyo
Biological and Pharmaceutical Bulletin 37(2), 262-267, 2014
… Then, marker substances of various molecular weights (phenolsulfonphthalein, fluorescein isothiocyanate-dextran (FD)-10, FD-40, FD-70, FD-2000 or tetramethylrhodamine-dextran (RD)-10) were injected into the peritoneal cavity. …
NAID 130003390929

Dietary fat and bile juice, but not obesity, are responsible for the increase in small intestinal permeability induced through the suppression of tight junction protein expression in LETO and OLETF rats

Suzuki Takuya,Hara Hiroshi
Nutrition & Metabolism 7, 19, 2010-03-12
… Intestinal permeability in the OLETF rats evaluated by the urinary excretion of intestinal permeability markers (Cr-EDTA and phenolsulfonphthalein) was comparable to that in the LETO rats. …
NAID 120002063215

Related Pictures

★リンクテーブル★

リンク元	「PSP」「フェノールスルホンフタレイン」「phenol red」
拡張検索	「phenolsulfonphthalein test」

「PSP」

Phenol red
Identifiers
CAS Registry Number	143-74-8
ATC code	V04CH03
ChEBI	CHEBI:31991
ChEMBL	ChEMBL258921
ChemSpider	4602
	InChI InChI=1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H ; Key: BELBBZDIHDAJOR-UHFFFAOYSA-N ;
Jmol-3D images	Image
PubChem	4766
	SMILES O=S2(=O)OC(c1ccccc12)(c3ccc(O)cc3)c4ccc(O)cc4 ;
Properties
Chemical formula	C19H14O5S
Molar mass	354.38 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

「フェノールスルホンフタレイン」

　　[★]

英: phenolsulfonphthalein PSP
同: フェノールレッド phenol red

「phenol red」

　　[★]

フェノールレッド

関: phenolsulfonphthalein

「phenolsulfonphthalein test」

　　[★] フェノールスルホンフタレイン色素排泄試験 PSP test

[merck-1] Merck Index, 11th ed., 7213 Phenolsulfonphtalein

[Merck-2] Merck Index, 13th ed., 7329 Phenolsulfonphthalein

[Beilstein-3] Beilstein 5-19-03-00457

[4] Tamura, Z.; Maeda M. (1997). "Differences between phthaleins and sulfonphthaleins". Yakugaku Zasshi (in Japanese) 117 (10–11): 764–770. PMID 9414589.

[5] "Phenolsulfonphthalein". PubChem. NIH.

[6] Yamaguchi, K.; Tamura, Z.; Maeda, M. (1997). "Molecular Structure of the Zwitterionic Form of Phenolsulfonphthalein" (pdf). Analytical Sciences 13 (3): 521–522. doi:10.2116/analsci.13.521.

[7] "Phenolsulfonphthalein Test". Encyclopædia Britannica.

[8] Berthois, Y.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. (1986). "Phenol red in tissue culture media is a weak estrogen: Implications concerning the study of estrogen-responsive cells in culture" (pdf). Proceedings of the National Academy of Sciences of the United States of America 83 (8): 2496–2500. doi:10.1073/pnas.83.8.2496. PMC 323325. PMID 3458212.

[9] Bukovsky, A.; Svetlikova, M.; Caudle, M. R. (2005). "Oogenesis in Cultures Derived from Adult Human Ovaries" (pdf). Reproductive Biology and Endocrinology 3 (5): 17. doi:10.1186/1477-7827-3-17. PMC 1131924. PMID 15871747.

[10] Guardex Solution 2 - Phenol Red Material Safety Data Sheet

[11] Effect of Bromine on Phenol Red in pH Tests

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phenolsulfonphthalein