10170-03-3

Basic information

• Product Name: UROPORPHYRIN I, OCTAMETHYL ESTER
• Synonyms: 21H,23H-Porphine-2,7,12,17-tetrapropanoic acid, 3,8,13,18-tetrakis(2-methoxy-2-oxoethyl)-, tetramethyl ester;23h-porphine-2,7,12,17-tetrapropanoicacid,3,8,13,18-tetrakis(2-methoxy-2-21;tetramethylester;UROPORPHYRIN I, OCTAMETHYL ESTER;tetramethyl 3,8,13,18-tetrakis(2-methoxy-2-oxoethyl)-21H,23H-porphine-2,7,12,17-tetrapropionate;3,8,13,18-Tetrakis(2-methoxy-2-oxoethyl)-21H,23H-porphyrin-2,7,12,17-tetrapropionic acid tetramethyl ester;3,8,13,18-Tetrakis(2-oxo-2-methoxyethyl)-21H,23H-porphyrin-2,7,12,17-tetrapropionic acid tetramethyl ester;3,8,13,18-Tetrakis[(methoxycarbonyl)methyl]-21H,23H-porphyrin-2,7,12,17-tetrakis(propanoic acid methyl) ester
• CAS NO: 10170-03-3
• Molecular Formula: C₄₈H₅₄N₄O₁₆
• Molecular Weight: 942.96
• EINECS: 233-444-0
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Porphyrins;porphine (porphyrin) ligand
• Mol File: 10170-03-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 291-292°C
• Boiling Point: 1153.1°Cat760mmHg
• Flash Point: 651.2°C
• Appearance: rust colored/Powder
• Density: 1.293g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: −20°C
• CAS DataBase Reference: UROPORPHYRIN I, OCTAMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: UROPORPHYRIN I, OCTAMETHYL ESTER(10170-03-3)
• EPA Substance Registry System: UROPORPHYRIN I, OCTAMETHYL ESTER(10170-03-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 10170-03-3(Hazardous Substances Data)

Usage

Description

UROPORPHYRIN I, OCTAMETHYL ESTER is a derivative of Uroporphyrin I (U847058), a porphyrin derivative with anti-HIV-1 activity. It is known for its ability to bind to the V3 loop of the envelope glycoprotein gp120 of the human immunodeficiency virus type 1. UROPORPHYRIN I, OCTAMETHYL ESTER is also utilized as a reagent for measuring the antioxidant capacity in biological samples, making it a valuable tool in various research and diagnostic applications.

Uses

Used in Pharmaceutical Industry:
UROPORPHYRIN I, OCTAMETHYL ESTER is used as an anti-HIV-1 agent for its ability to bind to the V3 loop of the envelope glycoprotein gp120, potentially inhibiting the virus's ability to infect host cells.
Used in Research and Diagnostic Applications:
UROPORPHYRIN I, OCTAMETHYL ESTER is used as a reagent for measuring the antioxidant capacity in biological samples, which is crucial for understanding the role of antioxidants in various diseases and the effectiveness of antioxidant therapies.
Used in Antiviral Applications:
In the field of antiviral research, UROPORPHYRIN I, OCTAMETHYL ESTER is used for its potential role in developing new treatments and therapies against HIV-1, by targeting the virus's envelope glycoprotein and disrupting its interaction with host cells.

InChI:InChI=1/C48H54N4O16/c1-61-41(53)13-9-25-29(17-45(57)65-5)37-22-34-27(11-15-43(55)63-3)31(19-47(59)67-7)39(51-34)24-36-28(12-16-44(56)64-4)32(20-48(60)68-8)40(52-36)23-35-26(10-14-42(54)62-2)30(18-46(58)66-6)38(50-35)21-33(25)49-37/h21-24,49-50H,9-20H2,1-8H3/b33-21-,34-22-,35-23-,36-24-,37-22-,38-21-,39-24-,40-23-

Upstream product

• 67-56-1 methanol 
• 607-14-7 uroporphyrin I 
• 84290-87-9 5'-formyl-3',4-di-(2-methoxycarbonylethyl)-3,4'-dimethoxycarbonylmethyl-2,2'-methylenedipyrrole-5-carboxylic acid 
• 77929-50-1 5'-formyl-4-methyl-3,3'-di-(2-methoxycarbonylethyl)-4'-(methoxycarbonylmethyl)-2,2'-methylenedipyrrole-5-carboxylic acid 
• 77813-88-8 uroporphyrinogen I octamethyl ester 
• 106-60-5 ALA 

Downstream Products

• 531-14-6 coproporphyrin I 
• 25767-20-8 coproporphyrin I methyl ester 
• 15435-60-6 uroporphyrin II octamethyl ester 
• 15435-60-6 uroporphyrin III octamethyl ester 

Relevant articles and documents

Isomerization of uroporphyrinogen I octamethyl ester through spiro- pyrrolenine intermediate

Treatment of uroporphyrinogen I octamethyl ester with 2- mercaptobenzothiazolylmethyl pyrrole derivative in the presence of silver (I) trifrate under anaerobic condition in dichloromethane for 20 h, followed by aerial oxidation of the products, gave a statistical mixture of uroporphyrin I~IV octamethyl esters. It was proposed that this transformation proceeds through a spiro-pyrrolenine as a key intermediate.

Identification of tetrapyrrole compounds excreted by Rhodobacter sphaeroides and sources of the methyl hydrogens of bacteriochlorophyll a biosynthesized by R. sphaeroides, based on13C-NMR spectral analysis of coproporphyrin III tetramethyl ester

Red-fluorescent tetrapyrrole compounds excreted by Rhodobacter sphaeroides into the culture broth were concluded to be coproporphyrinogen (Copro'gen) III and uroporphyrinogen (Uro'gen) I, based on the 13C-NMR spectral identification of coproporphyrin (Copro) III tetramethyl ester and uroproporphyrin (Uro) I octamethyl ester. The sources of the methyl hydrogens of bacteriochlorophyll a were established by analysis of the 13C-NMR spectra of 2H,13C-Copro III tetramethyl ester chemically derived from 2H,13C-Copro'gen III biosynthesized through the feeding of δ-amino[2-13C]levulinic acid (ALA) to R. sphaeroides in medium containing 50% 2H2O. We confirmed the previous finding that one of the methyl hydrogens was derived from water in the medium during decarboxylation of four acetyl side chains of Uro'gen III to generate Copro'gen III. It was further shown that the other hydrogen atoms, previously reported to be derived from methylene hydrogens at C-2 of ALA, had been exchanged with hydrogen of water in the medium in the biosynthetic pathways leading from ALA to Copro'gen III.

Quantitative analysis of porphyrins in dried blood spots using liquid chromatography-tandem mass spectrometry with pre-column derivatization

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