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P8293

Sigma-Aldrich

Protoporphyrin IX

≥95%

Synonym(s):

3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid, Kammerer’s porphyrin, Ooporphyrin

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About This Item

Empirical Formula (Hill Notation):
C34H34N4O4
CAS Number:
553-12-8
Molecular Weight:
562.66
Beilstein:
380795
EC Number:
209-033-7
MDL number:
MFCD00151109
UNSPSC Code:
41106305
PubChem Substance ID:
24278655
NACRES:
NA.32

Quality Level

100

Assay

≥95%

form

powder

fluorescence

λex 402 nm; λem 625 nm (bound to HRP)
λex 409 nm; λem 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

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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.

related product

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Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Agata Szade et al.
EMBO molecular medicine, 11(12), e09571-e09571 (2019-11-12)
Granulocyte colony-stimulating factor (G-CSF) is used in clinical practice to mobilize cells from the bone marrow to the blood; however, it is not always effective. We show that cobalt protoporphyrin IX (CoPP) increases plasma concentrations of G-CSF, IL-6, and MCP-1
Heme controls ferroportin1 (FPN1) transcription involving Bach1, Nrf2 and a MARE/ARE sequence motif at position -7007 of the FPN1 promoter.
Marro S
Haematologica, 95(8), 1261-1268 (2010)
J Flemmig et al.
Free radical research, 50(12), 1386-1395 (2016-10-26)
Excessive release of hemoglobin from red blood cells markedly disturbs the health status of patients due to cytotoxic effects of free hemoglobin and heme. The latter component is able to initiate novel hemolytic events in unperturbed red blood cells. We
Aggregation Behavior of Protoporphyrin IX in Aqueous Solutions: Clear Evidence of
Vesicle Formation
Luigi Monsu Scolaro
The Journal of Physical Chemistry B, 106, 2453-2459 (2002)
Johan Lindgren et al.
Scientific reports, 7(1), 13324-13324 (2017-10-19)
The holotype (MHM-K2) of the Eocene cheloniine Tasbacka danica is arguably one of the best preserved juvenile fossil sea turtles on record. Notwithstanding compactional flattening, the specimen is virtually intact, comprising a fully articulated skeleton exposed in dorsal view. MHM-K2
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