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| | Protoporphyrin IX Basic information |
| Product Name: | Protoporphyrin IX | | Synonyms: | KAMMERER'S PORPHYRIN;2,18-Porphinedipropionic acid, 3,8,13,17-tetramethyl-7,12-divinyl-;21H,23H-Porphine-2,18-dipropanoic acid, 7,12-diethenyl-3,8,13,17-tetramethyl-;7,12-Diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid;Kammerer's prophyrin;PROTOPORPHYRIN-'IX', FOR FLUORESCENCE;ProtoporphyrinIXforfluorescence95+%;PROTOPORPHYRINIX,FREEACID | | CAS: | 553-12-8 | | MF: | C34H34N4O4 | | MW: | 562.66 | | EINECS: | 209-033-7 | | Product Categories: | Inhibitors;Natural Porphyrins and Derivitives;Porphyrins;porphine (porphyrin) ligand | | Mol File: | 553-12-8.mol |  |
| | Protoporphyrin IX Chemical Properties |
| 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 | | InChIKey | FEDYMSUPMFCVOD-UJJXFSCMSA-N | | CAS DataBase Reference | 553-12-8 | | NIST Chemistry Reference | Protoporphyrin-1x(553-12-8) | | EPA Substance Registry System | Protoporphyrin IX (553-12-8) |
| | Protoporphyrin IX Usage And Synthesis |
| Uses | hepatoprotectant | | Uses | 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
| | 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. |
| | Protoporphyrin IX Preparation Products And Raw materials |
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