Porphobilinogen

Base Information

• Chemical Name: Porphobilinogen
• CAS No.: 487-90-1
• Deprecated CAS: 1189314-12-2,2118404-09-2
• Molecular Formula: C10H14 N2 O4
• Molecular Weight: 226.232
• Hs Code.: 2933990090
• European Community (EC) Number: 207-666-3
• UNII: 74KHC72QXK
• DSSTox Substance ID: DTXSID4060070
• Nikkaji Number: J6.026G
• Wikipedia: Porphobilinogen
• Wikidata: Q421178
• Metabolomics Workbench ID: 37157
• ChEMBL ID: CHEMBL1235151
• Mol file: 487-90-1.mol

Synonyms:Porphobilinogen

Chemical Property of Porphobilinogen

Chemical Property:

• Vapor Pressure: 5.74E-10mmHg at 25°C
• Melting Point: 174-177oC
• Boiling Point: 478.6ºC at 760 mmHg
• PKA: 4.22±0.10(Predicted)
• Flash Point: 243.2ºC
• PSA: 116.41000
• Density: 1.421g/cm3
• LogP: 0.81800
• Storage Temp.: −20°C
• Solubility.: Aqueous Base (Slightly), Acetonitrile (Slightly), DMSO (Slightly)
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 226.09535693
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

98%,99%, ^*data from raw suppliers

Porphobilinogen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O
• Uses: An intermediate in the biosynthesis of Heme, found in the urine of patients with acute porphyria.

Technology Process of Porphobilinogen

There total 30 articles about Porphobilinogen 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: 83.0%

3-(5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)-propionic acid ethyl ester (24331-86-0) → porphobilinogen (487-90-1)

Guidance literature:

With potassium hydroxide; In acetic acid; at 0 ℃; for 4h;

Reference yield: 59.0%

3-(5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid, methyl ester (32682-61-4) → porphobilinogen (487-90-1)

Guidance literature:

With potassium hydroxide; at 20 ℃; for 96h;

DOI:10.1021/ja016303q

Reference yield: 56.0%

5-aminolevulinic acid hydrochloride (5451-09-2) → porphobilinogen (487-90-1)

Guidance literature:

With potassium phosphate; 2-hydroxyethanethiol; 5-aminolevulinate dehydratase; 1.) 37 deg C, 6 h, 2.) pH 8.0, 0-4 deg C, overnight;

upstream raw materials:

ALA

porphobilinogen lactam

methanol

5-aminolevulinic acid hydrochloride

Downstream raw materials:

3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane

coproporphyrinogen III

protoporphyrin IX

uroporphyrinogen I

Refernces

• 1、 Battersby et al.. "-". . p. 451,453,454. Retrieved 1979.
• 2、 Choiniere, John R.,Scott, C. Ronald,Gelb, Michael H.,Turecek, Frantisek. "Direct assay of δ-Aminolevulinic acid dehydratase in heme biosynthesis for the detection of porphyrias by tandem mass spectrometry". . p. 6730 - 6736. Retrieved 2010.
• 3、 Jacobi,Li. "Synthesis of porphobilinogen via a novel ozonide cleavage reaction". . p. 9307 - 9312. Retrieved 2001.
• 4、 Müller,Bezold. "Production of porphobilinogen from delta-aminolevulinic acid with cell suspensions from Propionibacterium shermanii". . p. 47 - 53. Retrieved 1969.
• 5、 Donegan, Rebecca K.,Moore, Courtney M.,Hanna, David A.,Reddi, Amit R.. "Handling heme: The mechanisms underlying the movement of heme within and between cells". . p. 88 - 100. Retrieved 2018/08/21.