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Dichlorophenolindophenol

Names
Preferred IUPAC name 4-(3,5-dichloro-4-hydroxyphenyl)iminocyclohexa-2,5-dien-1-one
Other names Dichloroindophenol (); 2,6-Dichlorophenolindophenol; 2,6-Dichloroindophenol; 2,6-Dichloro-4-[(4-hydroxyphenyl)imino]-2,5-cyclohexadien-1-one
Identifiers
CAS Number	956-48-9 Y
3D model (JSmol)	Interactive image
Abbreviations	DCPIP, DCIP, DPIP
ChEBI	CHEBI:945 Y
ChEMBL	ChEMBL500871 Y
ChemSpider	10661857
ECHA InfoCard	100.012.254
EC Number	213-479-8
KEGG	C00102 Y
PubChemCID	13726
UNII	C35QN2Z58B
CompTox Dashboard(EPA)	DTXSID501174455 DTXSID7061352, DTXSID501174455
InChI InChI=1S/C12H7Cl2NO2/c13-10-5-8(6-11(14)12(10)17)15-7-1-3-9(16)4-2-7/h1-6,16H Y Key: CCBICDLNWJRFPO-UHFFFAOYSA-N Y InChI=1/C12H7Cl2NO2/c13-10-5-8(6-11(14)12(10)17)15-7-1-3-9(16)4-2-7/h1-6,16H Key: CCBICDLNWJRFPO-UHFFFAOYAL
SMILES Cl\C2=CC(=N/c1ccc(O)cc1)/C=C(/Cl)C2=O
Properties
Chemical formula	C12H7Cl2NO2
Molar mass	268.09 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302,H315,H319,H335
Precautionary statements	P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

2,6-Dichlorophenolindophenol (DCPIP,DCIP orDPIP) is achemical compound used as aredox dye. Whenoxidized, DCPIP is blue with a maximal absorption at 600 nm; whenreduced, DCPIP is colorless.

DCPIP can be used to measure the rate ofphotosynthesis. It is part of theHill reagents family. When exposed to light in a photosynthetic system, the dye is decolorised by chemical reduction. DCPIP has a higheraffinity for electrons thanferredoxin and the photosynthetic electron transport chain can reduce DCPIP as a substitute forNADP⁺, that is normally the final electron carrier in photosynthesis. As DCPIP is reduced and becomes colorless, the resultant increase inlight transmittance can be measured using aspectrophotometer.

DCPIP can also be used as an indicator forvitamin C.^[1][2] If vitamin C, which is a good reducing agent, is present, the blue dye, which turns pink in acid conditions, is reduced to a colorless compound by ascorbic acid. This reaction is a redox reaction: vitamin C (ascorbic acid) is oxidized todehydroascorbic acid, and DCPIP is reduced to the colorless compound DCPIPH₂

DCPIP (blue) + H⁺ → DCPIPH (pink)

DCPIPH (pink) + vitamin C → DCPIPH₂ (colorless)

In thistitration, when all the ascorbic acid in the solution has been used up, there will not be any electrons available to reduce the DCPIPH and the solution remains pink due to the DCPIPH. The end point is a pink color that persists for 10 seconds or more, if there is not enough ascorbic acid to reduce all of the DCPIPH. Pharmacological experiments suggest that DCPIP may serve as apro-oxidant chemotherapeutic targeting human cancer cells in an animal model of humanmelanoma; DCPIP-induced cancer cell death occurs by depletion of intracellularglutathione and upregulation ofoxidative stress.^[3]

• Indophenol
• Metachromasy
• Methylene blue
• Wurster's blue

• Indophenol dyes
• Redox indicators
• Chloroarenes
• 4-Hydroxyphenyl compounds

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