P8293

Protoporphyrin IX

≥95%

• Synonym(s): 3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid, Kammerer’s porphyrin, Ooporphyrin
• Empirical Formula (Hill Notation): C₃₄H₃₄N₄O₄
• CAS Number: 553-12-8
• Molecular Weight: 562.66
• Beilstein/REAXYS Number: 380795
• EC Number: 209-033-7
• MDL number: MFCD00151109
• UNSPSC Code: 41106305
• PubChem Substance ID: 24278655
• NACRES: NA.32

Properties

• assay: ≥95%
• form: powder
• fluorescence: λ_ex 402 nm; λ_em 625 nm (bound to HRP); λ_ex 409 nm; λ_em 633 nm
• storage temp.: 2-8°C
• SMILES string: Cc1c(CCC(O)=O)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(C)c5C=C)c(C)c4C=C)c(C)c3CCC(O)=O
• InChI: 1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
• InChI key: KSFOVUSSGSKXFI-UJJXFSCMSA-N

Description

General description

Protoporphyrin IX belongs to the porphyrin family, which are a class of tetrapyrroles. It is the iron-free form of hemin and amphiphilic in nature. It is the precursor of heme in its biosynthetic pathway.

Protoporphyrin IX imparts red color to heme and is the major porphyrin in blood. It is synthesized from protoporphyrinogen IX in the presence of protoporphyrinogen IX oxidase.

Application

Protoporphyrin IX has been used:

• as a standard in protoporphyrin assays
• in fluorescence spectra analysis
• to treat cells in cell culture to study heme-mediated ferroportin 1 transcription

Activates soluble guanylyl cyclase.

Biochem/physiol Actions

Protoporphyrin IX penetrates human erythrocytes and aids the release of oxygen from them. It forms complexes with myoglobin and hemoglobin. It is a photosensitizer used in the photodynamic therapy of cancer.

Protoporphyrin IX levels are elevated in tumor cells due to metabolism anomalies compared to normal cells.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves