5451-09-2 Usage
Description
5-Aminolevulinic acid hydrochloride is a hydrochloride that is the monohydrochloride of 5-aminolevulinic acid. It is a naturally occurring amino acid and serves as a precursor in the synthesis of tetrapyrroles such as chlorophyll and heme. It is metabolized to protoporphyrin IX, a photoactive compound that accumulates in the skin and is used in combination with blue light illumination for the treatment of various skin conditions.
Uses
Used in Photodynamic Therapy:
5-Aminolevulinic acid hydrochloride is used as a photosensitizer for the photodynamic therapy of diseases such as Paget's disease and human papillomavirus (HPV) infection-associated cervical condylomata acuminata. It aids in the treatment process by enhancing the effects of light-based therapies.
Used in Heme Biosynthesis:
5-Aminolevulinic acid hydrochloride is used as a supplement for culturing Escherichia coli cells for heme biosynthesis. It plays a crucial role in the production of heme, which is an essential component of hemoglobin and other biological processes.
Used in Pharmaceutical Industry:
As a precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme, 5-Aminolevulinic acid hydrochloride is used in the pharmaceutical industry for the development of drugs targeting various medical conditions.
Used in Skin Treatment:
5-Aminolevulinic acid hydrochloride is used in the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It is combined with blue light illumination to improve the effectiveness of the treatment.
Chemical Properties:
5-Aminolevulinic acid hydrochloride appears as white to pale yellow crystals.
Biochem/physiol Actions
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.
Purification Methods
Dry ALA-HCl in a vacuum desiccator over P2O5 overnight, then crystallise it by dissolving it in cold EtOH and adding dry Et2O. Also crystallis
Check Digit Verification of cas no
The CAS Registry Mumber 5451-09-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,5 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5451-09:
(6*5)+(5*4)+(4*5)+(3*1)+(2*0)+(1*9)=82
82 % 10 = 2
So 5451-09-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H
5451-09-2Relevant articles and documents
Convenient syntheses of δ-aminolevulinic acid
Nudelman, Ayelet,Nudelman, Abraham
, p. 568 - 570 (1999)
Two convenient procedures for the synthesis of δ-aminolevulinic acid (5-ALA) are described.
A convenient method for introducing oxo group into the β-position of cyclic amines and its application to synthesis of δ-aminolevulinic acid
Matsumura,Takeshima,Okita
, p. 304 - 306 (1994)
Oxo group could be introduced into the β-position of N-methoxycarbonylated cyclic amines by utilizing electrochemical oxidation and/or m-chloroperbenzoic acid oxidation, and this method was applied to the preparation of δ-aminolevulinic acid, an intermediate of chlorophyll biosynthesis.
Preparation method of 5-aminolevulinic acid hydrochloride
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Paragraph 0038; 0061; 0068-0069, (2021/11/03)
The invention discloses a preparation method of 5-aminolevulinic acid hydrochloride, which comprises the following steps: by taking 1, 3-dichloroacetone as an initial raw material, reacting with Meldrum's acid or a derivative thereof, then carrying out ester exchange, ammoniation reaction and hydrolysis decarboxylation, and finally decolorizing, concentrating and recrystallizing to obtain the 5-aminolevulinic acid hydrochloride. The method is high in yield, convenient to operate, stable in quality and suitable for industrial production.
Preparation method 5 - ALA intermediate 5 - bromoolevulinic acid ester
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Paragraph 0034; 0053; 0057, (2021/09/22)
The invention relates to a preparation method of 5 - ALA intermediate 5 - bromoacetyl ester, which is characterized by comprising the following steps: (S1) reaction of the urotropine and a bromine source to prepare the urotropine bromine complex. (S2) Lourotropine bromide complex and levulinic acid ester reaction. Gave 5 - bromoolevulinic acid ester. Compared with the prior art, a bromo reagent such as liquid bromine and 5 - is used directly, NBS-site bromination product yield is increased 5 - 10% or more. The defect that 3 -position bromination or multi-site bromination product is large and separation is difficult in the bromination reaction is overcome. The method is cheap and easily available in raw materials, simple and convenient to operate and suitable for large-scale preparation 5 - ALA intermediate 5 - bromolevulinic acid ester .