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PROTOPORPHYRIN IX
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Name

PROTOPORPHYRIN IX

 EINECS 209-033-7
CAS No. 553-12-8 Density 1.299 g/cm3
PSA 130.90000 LogP 4.04060
Solubility 106.9mg/L(25 oC) Melting Point >300 °C(Solv: acetone (67-64-1))
Formula C34H34N4O4 Boiling Point 1122.015 °C at 760 mmHg
Molecular Weight 562.668 Flash Point 632.372 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 553-12-8 (Protoporphyrin IX) Hazard Symbols IrritantXi
Synonyms

2,18-Porphinedipropionicacid, 3,8,13,17-tetramethyl-7,12-divinyl- (8CI);Protoporphyrin IX (6CI);Kammerer's porphyrin;Levulan;NSC 177389;NSC 2632;Ooporphyrin;Protoporphyrin;

Article Data 47

PROTOPORPHYRIN IX Synthetic route

5522-66-7

protoporphyrin IX dimethyl ester

553-12-8

protoporphyrin IX

Conditions
ConditionsYield
With potassium hydroxide In methanol Reflux; Inert atmosphere; Darkness;76.6%
With hydrogenchloride In water
With zinc diacetate In methanol; dichloromethane; chloroform; water
7412-77-3

harderoporphyrinogen IX

553-12-8

protoporphyrin IX

Conditions
ConditionsYield
With 1H-imidazole; Bacillus subtilis protoporphyrinogen oxidase; flavin adenine dinucleotide In phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.4; Enzyme kinetics; Further Variations:; Reagents;

hemin

553-12-8

protoporphyrin IX

Conditions
ConditionsYield
With ammonium hydroxide; phosphoric acid tributyl ester; sulfuric acid In benzene at 40℃; for 1.5h;
67-56-1

methanol

553-12-8

protoporphyrin IX

5522-66-7

protoporphyrin IX dimethyl ester

Conditions
ConditionsYield
With sulfuric acid at -10℃; for 18h;95%
553-12-8

protoporphyrin IX

N-(2-aminoethyl)maleimide trifluoroacetate

C46H46N8O6

Conditions
ConditionsYield
Stage #1: protoporphyrin IX With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 4h;
Stage #2: N-(2-aminoethyl)maleimide trifluoroacetate In N,N-dimethyl-formamide at 20℃; for 5h;		73%
67-56-1

methanol

553-12-8

protoporphyrin IX

297162-50-6

20-amino-3,6,9,12,15,18-hexaoxaeicosanoic acid tert-butyl ester

C54H71N5O12

Conditions
ConditionsYield
Stage #1: protoporphyrin IX With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Inert atmosphere;
Stage #2: methanol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
Stage #3: 20-amino-3,6,9,12,15,18-hexaoxaeicosanoic acid tert-butyl ester Further stages;		72%
1402836-58-1

rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole

553-12-8

protoporphyrin IX

C52H54N6O4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 60℃; for 5h;65.8%
553-12-8

protoporphyrin IX

75-65-0

tert-butyl alcohol

3-[(1Z,5Z,9Z,14Z)-18-(2-tert-Butoxycarbonyl-ethyl)-3,7,12,17-tetramethyl-8,13-divinyl-22,24-dihydro-porphin-2-yl]-propionic acid

Conditions
ConditionsYield
Stage #1: protoporphyrin IX With dmap; di-tert-butyl dicarbonate In pyridine at 20℃; for 6h;
Stage #2: tert-butyl alcohol In pyridine at 20℃; for 1h; Further stages.;		64%
With pyridine; dmap at 20℃;64%
86520-52-7

2-[2-(2-azidoethoxy)ethoxy]ethanol

553-12-8

protoporphyrin IX

C40H45N7O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;58%
553-12-8

protoporphyrin IX

100-51-6

benzyl alcohol

A

6-[2'-(benzyloxycarbonyl)ethyl]-7-(2'-carboxyethyl)-1,3,5,8-tetramethyl-2,4-divinylporphyrin

B

3-[(5Z,10Z,14Z,19Z)-18-(2-Benzyloxycarbonyl-ethyl)-3,8,13,17-tetramethyl-7,12-divinyl-porphyrin-2-yl]-propionic acid benzyl ester

Conditions
ConditionsYield
Stage #1: protoporphyrin IX With pyridine; pivaloyl chloride; triethylamine In dichloromethane at -5℃;
Stage #2: benzyl alcohol In dichloromethane at 5 - 8℃; for 12h;		A 47%
B 18%
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