33320-16-0

Basic information

• Product Name: D-Aminolevulinicacidmethylesterhydrochloride
• Synonyms: D-AminolevulinicacidmethylesterHCl;methyl 5-amino-4-oxopentanoate;methyl 5-aminolevulinate
• CAS NO: 33320-16-0
• Molecular Formula: C6H12ClNO3
• Molecular Weight: 181.61738
• Mol File: 33320-16-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 228 °C at 760 mmHg
• Flash Point: 99.5 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.0937mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: D-Aminolevulinicacidmethylesterhydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: D-Aminolevulinicacidmethylesterhydrochloride(33320-16-0)
• EPA Substance Registry System: D-Aminolevulinicacidmethylesterhydrochloride(33320-16-0)

Safety Data

• Hazardous Substances Data: 33320-16-0(Hazardous Substances Data)

Usage

Definition

ChEBI: The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydro hloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills t e tumour cells.

InChI:InChI=1/C6H11NO3/c1-4(8)3-5(7)6(9)10-2/h5H,3,7H2,1-2H3

Upstream product

• 624-45-3 levulinic acid methyl ester 
• 106-60-5 ALA 
• 149-73-5 trimethyl orthoformate 

Relevant articles and documents

Photosensitizer prodrug compound, and preparation method and application thereof

The invention provides a photosensitizer prodrug compound, and a preparation method and an application thereof. The compound has a structure represented by formula (I). A disulfide bond is introduced at the N end of 5-ALA or its ester derivative, the disulfide bond is a GSH responsive group, the group containing the disulfide bond undergoes self-immolative reaction under the condition of linking urethane to the beta position of the disulfide bond in order to release the connected 5-ALA or its ester derivative, protoporphyrin is generated in an intracellular metabolism manner, and the photosensitizer plays a role in photodynamic diagnosis, so dimerization induced inactivation of the 5-ALA is avoided, and the drug stability is increased; and the overexpression of the GSH in various tumor cells and the response of the prodrug compound to the GSH enhance the tumor targeting property of the drug. The invention also provides the application of the photosensitizer prodrug compound in the preparation of the drug for photodynamic diagnosis and treatment.

Improved peptide prodrugs of 5-ALA for PDT: Rationalization of cellular accumulation and protoporphyrin IX production by direct determination of cellular prodrug uptake and prodrug metabolization

Twenty-seven dipeptide derivatives of general structure Ac-Xaa-ALA-OR were synthesized as potential prodrugs for 5-aminolaevulinic acid-based photodynamic therapy (ALA-PDT). Xaa is an R-amino acid, chosen to provide a prodrug with appropriately tailored l