Hematoporphyrin

Base Information

• Chemical Name: Hematoporphyrin
• CAS No.: 14459-29-1
• Deprecated CAS: 553-11-7,19710-66-8
• Molecular Formula: C34H38 N4 O6
• Molecular Weight: 598.699
• European Community (EC) Number: 238-450-7
• NSC Number: 267084,59265
• UNII: HBT6M5H379
• DSSTox Substance ID: DTXSID901030645,DTXSID00864508
• Nikkaji Number: J1.925.508E,J55.181C,J2.788.927A
• Wikipedia: Hematoporphyrin
• NCI Thesaurus Code: C167224
• Metabolomics Workbench ID: 55293
• ChEMBL ID: CHEMBL317840,CHEMBL403729
• Mol file: 14459-29-1.mol

Synonyms:Haematoporphyrin IX;Hematoporphyrin;Hematoporphyrins;Hemedonin

Chemical Property of Hematoporphyrin

Chemical Property:

• Melting Point: 172.5°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 1192.7°Cat760mmHg
• Flash Point: 675.1°C
• PSA: 171.36000
• Density: 1.32g/cm³
• LogP: 2.64570
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly), Methanol (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 598.27913494
• Heavy Atom Count: 44
• Complexity: 1020

Purity/Quality:

99% ^*data from raw suppliers

HP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic. Reported to be preferentially absorbed by cancerous tissues, making them fluoresce under UV light.
• Hazard Codes: Toxic. Reported to be preferentially absorbed by cancerous tissues, making them fluoresce under UV light.
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C2=CC3=NC(=CC4=NC(=CC5=C(C(=C(N5)C=C1N2)C(C)O)C)C(=C4CCC(=O)O)C)C(=C3C)CCC(=O)O)C(C)O
• Recent ClinicalTrials: Perio. Maint. With Diode LBR
• Uses: antidepressant, antineoplastic Hematoporphyrin (Photodyn, Sensibion) is a porphyrin prepared from hemin. It is a derivative of protoporphyrin IX, where the two vinyl groups have been hydrated (coverted to alcohols). It is used as a photosensitizer in photodynamic therapy. Acetylation of hematoporphyrin followed by hydrolysis of the product of that reaction affords a mixture called hematoporphyrin derivative (HPD), which is also used in photodynamic therapy. Hematoporphyrin has also been used as an antidepressant and antipsychotic since the 1920s.

Technology Process of Hematoporphyrin

There total 9 articles about Hematoporphyrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ hematoporphyrin (14459-29-1)

Guidance literature:

Dihydro-haematoporphyrin durch Disproportionierung;

DOI:10.1021/ja00871a032

Reference yield:

→ hematoporphyrin (14459-29-1) + hematoporphyrin-dimethyl ester (32562-61-1,119366-88-0,119366-89-1,131070-54-7,131070-74-1,6033-09-6)

Guidance literature:

Reference yield:

hemin → hematoporphyrin (14459-29-1)

Guidance literature:

With hydrogen bromide; acetic acid; hematoporphyrin-IX; anschliessend Behandeln mit H₂O;

upstream raw materials:

3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

diacetyldeuteroporphyrin IX dimethyl ester

hematoporphyrin-dimethyl ester

O,O'-diacetyl-hematoporphyrin-dimethyl ester

Downstream raw materials:

hematoporphyrin-dimethyl ester

protoporphyrin

3-[(1Z,4Z,9Z,15Z)-18-[3-(N,N'-Dicyclohexyl-carbamimidoyloxy)-3-oxo-propyl]-7,12-bis-(1-hydroxy-ethyl)-3,8,13,17-tetramethyl-porphyrin-2-yl]-propionic acid benzyl ester

3-[(4Z,10Z,15Z,19Z)-18-[3-(N,N'-Dicyclohexyl-carbamimidoyloxy)-3-oxo-propyl]-8,13-bis-(1-hydroxy-ethyl)-3,7,12,17-tetramethyl-22,24-dihydro-porphin-2-yl]-propionic acid benzyl ester

Refernces

A New Water-soluble Singlet Oxygen Probe

10.1039/c39820001147

The research aimed to synthesize a new water-soluble singlet oxygen probe, which is crucial for studying the formation and biological implications of singlet oxygen in aqueous media. The researchers synthesized a dihydroisobenzofuran derivative, specifically the potassium salt of (4,7-dihydro-5,6-dimethylisobenzofuran-1,3-diyl)bis(benzene-p-decanoic acid), known as DIBA. This compound was designed to overcome the limitations of previous water-soluble singlet oxygen traps, which had strong absorption in the visible region, complicating kinetic studies. The study concluded that DIBA is a suitable probe for singlet oxygen due to its rapid bleaching upon reaction, and the involvement of superoxide radicals in the bleaching process was indicated by the change in reaction rate in argon-saturated and deuteriated water solutions. Key chemicals used in the synthesis process included hematoporphyrin (HP) as a photosensitizer, and various reagents in the multi-step synthesis scheme such as EtO2C[CH2]2COCI, H2, Pd-C, MeCO2H-HCl, fumaroyl chloride, AlCl3, and KOH-EtOH.