5-Aminolevulinic acid methyl ester hydrochloride CAS 79416-27-6, 5-Aminolevulinic acid methyl ester hydrochloride, CAS 79416-27-6
5-aminolevulinic acid hydrochloride + anhydrous methanol (in a ratio of 1:5-8 g/mL) → Mix and dissolve;
79416-27-6
C6H12ClNO3
181.62
279-151-1
| CAS | 79416-27-6 |
| Molecular formula | C6H12ClNO3 |
| Molecular weight | 181.62 |
| EIENCS | 279-151-1 |
| Form | Solid |
| Melting point | 119-121°C |
| boling point | / |
| Density | / |
| Solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
| PKA | / |
| Color | White to Off-White |
| Storage temp | 2-8°C |
1. Mainstream craftsmanship
Catalytic esterification method (patent technology in 2024)
Steps
5-aminolevulinic acid hydrochloride + anhydrous methanol (in a ratio of 1:5-8 g/mL) → Mix and dissolve;
Add sulfoxide (SOCl₂, at a ratio of 1:1-1.5g /mL), and control the temperature at 5-10℃.
Heat to 60-70 ℃ and reflux for 3-5 hours;
Concentrate and recover methanol, and dissolve the solid powder in water.
Activated carbon decolorization (3-5% v/v, 50-70 ℃), cooling crystallization (rate 3-5 ℃/h).
Advantages: The yield is increased by 20%, the cost is reduced by 30%, and high ammonia nitrogen wastewater is avoided.
2. Comparison of traditional methods
Molecular sieve catalytic method: It requires high-temperature drying (300-350℃), has high energy consumption and low yield (Russian patent RU2611441C2).
1. Medical field (Core application)
Photodynamic therapy (PDT)
Mechanism of action: It is metabolized into protoporphyrin IX (PpIX), accumulates within cancer cells, and generates reactive oxygen species (ROS) under light exposure to kill tumor cells.
Advantages: It has a lipophilicity higher than 5-ALA, and its cell membrane penetration efficiency is increased by three times. It is suitable for the treatment of skin cancer and head and neck tumors.
2. Agriculture and Biotechnology
Plant growth regulation: As a precursor of 5-ALA, it promotes chlorophyll synthesis and enhances photosynthesis (dosage: 0.1-1 mg/L).
Pesticide intermediates: Synthesize highly efficient and low-toxicity fungicides to replace traditional organophosphorus pesticides.
3. Chemical Engineering and Materials
Organic synthesis: Preparation of porphyrin compounds and ionic liquid carriers.
Cosmetic additives: Repair skin damaged by light, but the concentration should be controlled (<0.5%) to avoid irritation.
Toxicity and Risk
Irritation: Eye/skin/respiratory tract irritation (GHS05, H315/H319/H335).
Operation protection: Wear a dust mask and goggles, and operate in a fume hood.
Storage and transportation
Keep away from light and sealed at 2-8 ℃, away from oxidants.
Non-hazardous goods transportation (NONH), but must be protected from moisture and light.
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