Protoporphyrin IX
Synonym(s):3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid;8,13-Divinyl-3,7,12,17-tetramethyl-21H,23H-porphine-2,18-dipropionic acid zinc derivative;Kammerer’s porphyrin;Ooporphyrin;Protoporphyrin IX zinc(II) complex
- CAS NO.:553-12-8
- Empirical Formula: C34H34N4O4
- Molecular Weight: 562.66
- MDL number: MFCD00151109
- EINECS: 209-033-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is Protoporphyrin IX?
The Uses of Protoporphyrin IX
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
The Uses of Protoporphyrin IX
hepatoprotectant
What are the applications of Application
Protoporphyrin-9 is the key porphyrin precursor to heme sites and chlorophyll in animal and plant cells
Definition
ChEBI: A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyri s.
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.
Biochem/physiol Actions
Protoporphyrin IX?levels are elevated in?tumor?cells due to?metabolism anomalies?compared to normal?cells.
Enzyme inhibitor
This iiron-free, immediate precusor of heme (FWfree-acid = 562.67 g/mol; CAS 553-12-8; brownish-yellow solid; soluble in a number of organic solvents; disodium and dipotassium salts solublized in the presence of Tween 80) has lmax values in 25% HCl are 602.4, 582.2, and 557.2 nm. Protoporphryrin IX is also an activator of guanylate cyclase. See also Iron Protoporphyrin IX; Heme; Hemin Target(s): aminolevulinate aminotransferase; 5-aminolevulinate synthase; glutamate: glyoxylate aminotransferase; glutathione S-transferase; glyoxalase I, or lactoylglutathione lyase; guanylate cyclase; heme oxygenase; hydroxymethylbilane synthase, or porphobilinogen deaminase; nitric-oxide synthase; porphobilinogen synthase, or 5-aminolevulinate dehydratase; succinyl-CoA synthetase; tryptophan pyrrolase, or tryptophan 2,3-dioxygenase; and uroporphyrinogen decarboxylase.
Purification Methods
Protoporphyrin IX (3,18-divinyl-2,7,13,17-tetramethylporphin-8,12-dipropionic acid, ooporphyrin) [553-12-8] M 562.7, pKEst ~ 4.8. Protoporphyrin IX is purified by dissolving (4g) in 98-100% HCOOH (85mL), diluting with dry Et2O (700mL) and keeping at 0o overnight. The precipitate is collected and washed with Et2O, then H2O, and dried in a vacuum at 50o over P2O5. It crystallises from aqueous pyridine and from Et2O in monoclinic, brownish-yellow prisms. The UV max values in 25% HCl are 557.2, 582.2 and 602.4nm. It is freely soluble in ethanolic HCl, AcOH, CHCl3, and Et2O containing AcOH. It forms sparingly soluble diNa and diK salts. [Ramsey Biochemical Preparations 3 39 1953, UV: Holden Aust J. Exptl Biol and Med Sci 15 412 1937, Garnick J Biol Chem 175 333 1948, IR: Falk & Willis Aust J Sci Res [A] 4 579 1951, Beilstein 26 IV 3042.]
Toxicity evaluation
protoporphyrin IX, is highly toxic in the presence of light and molecular oxygen, killing photosynthetic plants very quickly through the generation of singlet oxygen.
Properties of Protoporphyrin IX
Melting point: | >300 °C(Solv: acetone (67-64-1)) |
Boiling point: | 629.06°C (rough estimate) |
Density | 1.1829 (rough estimate) |
refractive index | 1.6000 (estimate) |
storage temp. | 2-8°C |
solubility | DMSO (Slightly) |
form | Powder |
color | purple |
Water Solubility | 106.9mg/L(25 ºC) |
Sensitive | light sensitive |
Merck | 13,7990 |
BRN | 380795 |
Stability: | Light Sensitive |
CAS DataBase Reference | 553-12-8 |
NIST Chemistry Reference | Protoporphyrin-1x(553-12-8) |
EPA Substance Registry System | Protoporphyrin IX (553-12-8) |
Safety information for Protoporphyrin IX
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Protoporphyrin IX
InChIKey | FEDYMSUPMFCVOD-UJJXFSCMSA-N |
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