ChemicalBook CAS DataBase List 5-Aminolevulinic acid hydrochloride

5-Aminolevulinic acid hydrochloride synthesis

9synthesis methods

Product Name:5-Aminolevulinic acid hydrochloride
CAS Number:5451-09-2
Molecular formula:C5H10ClNO3
Molecular Weight:167.59

Aminolevulinic acid, also known as ALA, is a topically administered metabolic precursor of protoporphyrin IX. After topical administration, aminolevulinic acid (ALA) is converted to protoporphyrin IX (PpIX) which is a photosensitizer. When the proper wavelength of light activates protoporphyrin IX, singlet oxygen is produced, resulting in a local cytotoxic effect. In 1999, FDA approved this drug for for actinic keratosis.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Shrestha-dawadi, Prativa Bade; Lugtenburg, Johan. Preparation of [1,2,3,4,5-13C5]-5-amino-4-oxopentanoic acid (ALA) - design of a synthetic scheme to prepare any 13C- and 15N-isotopomer with high isotopic enrichment. European Journal of Organic Chemistry. Issue 23. Pages 4654-4663. 2003.

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Yield:5451-09-2 96.6%

Reaction Conditions:

with hydrogenchloride in water; for 6 h;Reflux;

Steps:

2.1; 2.1-1; 2.2; 2.1-2; 2.3-2.17; 2.1-3; 2.5.3; 3

Dissolve 2.00 g of 5-phthalimide levulinic acid obtained in the previous step with 40 ml of 6N hydrochloric acid and heat it for reaction at reflux for 6 hours, decolorize and filter on activated carbon, distill under reduced pressure to remove water to the end, and recrystallize the remainder with acetone , To obtain 1.24 g of solid. According to the proton nuclear magnetic resonance spectrum data, the obtained solid is determined to be 5-aminolevulinic acid hydrochloride, with a yield of 96.6% (calculated as 5-phthalimidolevulinic acid); mp: 149°C, purity ( HPLC, a/a%) 99.9%.

References:

CN111592484,2020,A Location in patent:Paragraph 0060; 0062-0063; 0065-0066; 0068-0069; 0071-0072