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+]
• Description: 5-aminolevulinic acid is the simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as a photosensitizing agent, an antineoplastic agent, a dermatologic drug, a prodrug, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a delta-amino acid and a 4-oxo monocarboxylic acid. It derives from a 4-oxopentanoic acid. It is a conjugate base of a 5-ammoniolevulinic acid. It is a conjugate acid of a 5-aminolevulinate. It is a tautomer of a 5-ammoniolevulinate.
• Uses: 5-Aminolevulinic acid (ALA), a nonprotein amino acid involved in tetrapyrrole synthesis, has been widely applied in agriculture, medicine, and food production.5-Aminolevulinic acid (5-ALA) is an intermediate in heme biosynthesis and is useful in cancer treatment. It is a non-protein amino acid. 5-ALA also has applications in the field of agriculture. It is being studied as an inducing reagent for protoporphyrin IX (PPIX) dependent fluorescence diagnosis of metastatic lymph nodes. 5-ALA is used for photodynamic therapy of diseases, such as Paget′s disease and HPV infection-associated cervical condylomata acuminata.Intermediate in heme biosynthesis.
• Indications: Aminolevulinic acid (ALA HCl, Levulan Kerastick) is indicated for the treatment of nonhyperkeratotic actinic keratosis of the face and scalp. It has two components, an alcohol solution vehicle and ALA HCl as a dry solid. The two are mixed prior to application to the skin. When applied to human skin, ALA is metabolized to protoporphyrin, which accumulates and on exposure to visible light produces a photodynamic reaction that generates reactive oxygen species (ROS).The ROS produce cytotoxic effects that may explain therapeutic efficacy. Local burning and stinging of treated areas of skin due to photosensitization can occur.
• Therapeutic Function: Photosensitizer

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:

methyl aminolevulinate

5-aminolevulinic acid phosphate

piperidine-2,5-dione

C₂₆H₄₃N₈O₁₈P₃S

Refernces

• 1、 Soares, Ana M. S.,Hungerford, Graham,Gon?alves, M. Sameiro T.,Costa, Susana P. G.. "Light triggering of 5-aminolevulinic acid from fused coumarin ester cages". . p. 2997 - 3005. Retrieved 2017.
• 2、 Lendrihas, Thomas,Hunter, Gregory A.,Ferreira, Gloria C.. "Serine 254 enhances an induced fit mechanism in murine 5-aminolevulinate synthase". . p. 3351 - 3359. Retrieved 2010.
• 3、 -. "Process for preparing 5-aminolevulinic acid from 5-chloromethyl furfural". Paragraph 0025; 0033-0036; 0043-0045; 0052-0054; 0061-0062. . Retrieved 2019/10/29.