5,10,15,20-TETRAKIS(4-HYDROXYPHENYL)-21H,23H-PORPHINE Chemical Properties

Melting point:

>300 °C(lit.)

Density 

1.401±0.06 g/cm3(Predicted)

storage temp. 

room temp

form 

powder to crystal

color 

Gray to Dark purple to Black

λmax

421 nm

ε(extinction coefficient)

≥285000 at 417-423nm in methanol at 0.001g/L

InChIKey

VFHDWGAEEDVVPD-LWQDQPMZSA-N

SMILES

C1(C2=CC=C(O)C=C2)=C2N=C(C(C3=CC=C(O)C=C3)=C3NC(=C(C4=CC=C(O)C=C4)C4=NC(=C(C5=CC=C(O)C=C5)C5NC1=CC=5)C=C4)C=C3)C=C2 |c:20,t:8,23,35|

Safety Information

Hazard Codes 

C

Risk Statements 

34-37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3263 8/PG 3

WGK Germany 

1

HS Code 

2934.30.5000

MSDS

• Language:English Provider:SigmaAldrich

5,10,15,20-TETRAKIS(4-HYDROXYPHENYL)-21H,23H-PORPHINE Usage And Synthesis

Description

5,10,15,20-(tetra-4-hydroxyphenyl)porphyrin is a porphyrin derivative used for detection of water-soluble vitamins by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry.

Uses

meso-Tetra(p-hydroxyphenyl)porphine is a porphyrin derivative used for research.

Synthesis

6.1 g of p-hydroxybenzaldehyde was dissolved in 110 mL of propionic acid, 6 mL of dimethyl sulfoxide (DMSO) was added, the mixture was mechanically stirred and heated to 128°C. Freshly distilled 3.5 mL of pyrrole was dissolved in 10 mL of propionic acid and slowly added dropwise at a rate of 1 drop per second to the above reaction mixture. The temperature of the reaction system was then raised to 141 °C and the reaction was refluxed for 2 hours. Upon completion of the reaction, hot filtration was performed and the filter cake was washed twice with propionic acid to obtain a blue solid 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin crude product. 10 g of the dried crude product was placed in a 100 mL round-bottomed flask, 20 mL of anhydrous ethanol was added and heated to reflux for 15 minutes before continuing to heat for 1.5 hours. The reaction solution was cooled in an ice bath for 1.5 h. The reaction solution was filtered and washed twice with ethanol to give 0.6172 g of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin in 7.27% yield. Finally, the purified product was purified by silica gel column chromatography (200 mesh) using acetone as eluent.

References

[1] Patent: CN105085536, 2018, B. Location in patent: Paragraph 0060; 0117-0122
[2] Journal of the American Chemical Society, 2013, vol. 135, # 49, p. 18513 - 18519
[3] Macromolecular Bioscience, 2013, vol. 13, # 6, p. 808 - 816
[4] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 611 - 623
[5] Tetrahedron Letters, 2007, vol. 48, # 41, p. 7287 - 7290

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