Protoporphyrin IX

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 Structure
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
InChIKeyFEDYMSUPMFCVOD-UJJXFSCMSA-N
CAS DataBase Reference553-12-8
NIST Chemistry ReferenceProtoporphyrin-1x(553-12-8)
EPA Substance Registry SystemProtoporphyrin IX (553-12-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
8-10-23
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Protoporphyrin IX Usage And Synthesis
Useshepatoprotectant
UsesProtoporphyrin 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
DefinitionChEBI: 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 DescriptionProtoporphyrin 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 ActionsProtoporphyrin IX?levels are elevated in?tumor?cells due to?metabolism anomalies?compared to normal?cells.
Enzyme inhibitorThis 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 MethodsProtoporphyrin 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 evaluationprotoporphyrin 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
Preparation ProductsProtoporphyrin IX dimethyl ester-->Cu(II) Protoporphyrin IX
PROTOPORPHYRINATO ZINC PROTOPORPHYRIN-'IX' DISODIUM SALT,PROTOPORPHYRIN IX DISODIUM SALT,PROTOPORPHYRIN-'IX' DISODIUM SALT, FOR F LUORESCENCE,DISODIUM PROTOPORPHYRIN IX Protoporphyrin IX Hyaluronic acid 2,2-Bis(hydroxymethyl)propionic acid Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid Hematoprophyrin Folic acid 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE VINYL PROPIONATE CHLORODIMETHYLVINYLSILANE N-METHYL PROTOPORPHYRIN IX Silicone rubber,methyl-vinyl PROTOPORPHYRIN IX V(IV) OXIDE Vinyl resin chromium protoporphyrin IX Citric acid Protoporphyrin

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