5-Azaniumyl-4-oxopentanoate

Base Information

• Chemical Name: 5-Azaniumyl-4-oxopentanoate
• CAS No.: 106-60-5
• Molecular Formula: C5H9NO
• Molecular Weight: 131.131
• Hs Code.: 29225090
• Mol file: 106-60-5.mol

Synonyms:5-azaniumyl-4-oxopentanoate;delta-aminolevulinate;5-ammoniolevulinate;5-ammonio-4-oxovalerate;5-ammonio-4-oxopentanoate;CHEBI:356416

Chemical Property of 5-Azaniumyl-4-oxopentanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.000303mmHg at 25°C
• Melting Point: 118-119 °C
• Refractive Index: 1.481
• Boiling Point: 298.4 °C at 760 mmHg
• PKA: 4.05(at 25℃)
• Flash Point: 134.3 °C
• PSA: 80.39000
• Density: 1.231 g/cm³
• LogP: 0.07930
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

3,4-Bis(benzyloxy)benzaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(=O)[O-])C(=O)C[NH3+]
• General Description: 5-Amino-4-oxopentanoic acid (also known as aminolevulinic acid or ALA) is a key intermediate in the biosynthesis of tetrapyrrole macrocycles, such as porphyrins, which are essential for bioenergetic processes. In prebiotic chemistry, ALA has been demonstrated to react with other acyclic compounds under moderate conditions to form uroporphyrinogen, bypassing the need for porphobilinogen (PBG) and suggesting a plausible abiotic pathway for the synthesis of these critical macrocycles. This highlights its potential role in the origin of life and the formation of biologically significant molecules.

Technology Process of 5-Azaniumyl-4-oxopentanoate

There total 38 articles about 5-Azaniumyl-4-oxopentanoate 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: 92.0%

C8H13NO4 → ALA (106-60-5)

Guidance literature:

With hydrogenchloride; cholesterol; In water; at 80 ℃; pH=7.2;

Reference yield: 87.0%

C8H15NO3 → ALA (106-60-5)

Guidance literature:

With hydrogenchloride; cholesterol; In water; at 70 ℃; pH=7.5;

Reference yield: 84.0%

C12H20ClNO3 → ALA (106-60-5)

Guidance literature:

With hydrogenchloride; cholesterol; In water; at 60 ℃; pH=7.8;

upstream raw materials:

5-hydroxyimino-4-oxo-valeric acid

5-phthalimidyl levulinic acid

ethyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate

2-Benzoylamino-3-oxo-hexanedioic acid 1-ethyl ester

Downstream raw materials:

porphobilinogen

3-[5-(2-Methoxycarbonyl-ethyl)-pyrazin-2-yl]-propionic acid methyl ester

3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid

pseudo-porphobilinogen

Refernces

Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

10.1039/c0nj00716a

The research focuses on the abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants, which are key precursors in the biosynthesis of tetrapyrrole macrocycles like porphyrins. These macrocycles are essential in various bioenergetic processes and are considered crucial for the origin of life. The study aimed to identify plausible prebiotic routes for forming these macrocycles, particularly addressing the challenge of forming the pyrrole precursor, porphobilinogen (PBG). The researchers successfully demonstrated a structure-directed route where d-aminolevulinic acid (ALA) reacts with 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH) under anaerobic conditions in water at moderate temperatures and pH levels, yielding uroporphyrinogen. This process bypasses the need for PBG, a significant hurdle in prebiotic chemistry, and suggests a possible prebiotic pathway for the formation of tetrapyrrole macrocycles. The study also showed that a different precursor could lead to the formation of coproporphyrinogen without the intermediacy of uroporphyrinogen. The chemicals used in this process include ALA, 1-AcOH, and their decarboxy analogues, which under specific conditions, resulted in the formation of uroporphyrinogen and coproporphyrinogen, respectively.