Aminolevulinic Acid hydrochloride
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Aminolevulinic Acid hydrochloride

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Aminolevulinic Acid 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. It is an intermediate in heme biosynthesis and photochemotherapy for actinic keratosis.

Category
Other Unnatural Amino Acids
Catalog number
BAT-008154
CAS number
5451-09-2
Molecular Formula
C5H10ClNO3
Molecular Weight
167.59
Aminolevulinic Acid hydrochloride
Size Price Stock Quantity
10 g $197 In stock
IUPAC Name
5-amino-4-oxopentanoic acid;hydrochloride
Synonyms
Levulan Kerastick; 5-Aminolevulinic acid HCl; 5-ALA; NSC-18509; Gliolan; delta-Aminolevulinic acid hydrochloride
Related CAS
106-60-5 (free base)
Appearance
White to Off-White Solid
Purity
>98%
Density
1.2±0.1 g/cm3
Melting Point
156-158°C
Boiling Point
311.5±27.0 °C at 760 mmHg
Storage
Store at -20°C
Solubility
Soluble in DMSO, Methanol and Water
Application
photochemotherapy for actinic keratosis
InChI
InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H
InChI Key
ZLHFONARZHCSET-UHFFFAOYSA-N
Canonical SMILES
C(CC(=O)O)C(=O)CN.Cl
1.Urinary 5-Aminolevulinic Acid Concentrations as a Potential Tumor Marker for Colorectal Cancer Screening and Recurrence.
Kamada Y1, Murayama Y2, Ota U3, Takahashi K3, Arita T1, Kosuga T1, Konishi H1, Morimura R1, Komatsu S1, Shiozaki A1, Kuriu Y1, Ikoma H1, Nakanishi M1, Ichikawa D1, Fujiwara H1, Okamoto K1, Tanaka T3, Otsuji E1. Anticancer Res. 2016 May;36(5):2445-50.
BACKGROUND/AIM: Tumor biomarkers, such as carcinoembryonic antigen (CEA) and cancer antigen 19-9 (CA19-9), are used to screen and monitor tumor recurrence in patients with colorectal cancer (CRC). 5-Aminolevulinic acid (5-ALA) is used in photodynamic diagnosis and therapy. Porphyrins produced by tumor cells are excreted in the urine after 5-ALA administration. In this study, we evaluated the use of porphyrins as novel tumor markers in urine samples from patients with CRC.
2.Intraoperative Detection of Superficial Liver Tumors by Fluorescence Imaging Using Indocyanine Green and 5-aminolevulinic Acid.
Kaibori M1, Matsui K2, Ishizaki M2, Iida H2, Okumura T2, Sakaguchi T2, Inoue K2, Ikeura T3, Asano H4, Kon M2. Anticancer Res. 2016 Apr;36(4):1841-9.
BACKGROUND/AIM: Indocyanine green (ICG) and the porphyrin precursor 5-aminolevulinic acid (5-ALA) have been approved as fluorescence imaging agents in the clinical setting. This study evaluated the usefulness of fluorescence imaging with both ICG and 5-ALA for intraoperative identification of latent small liver tumors.
3.A gas chromatography-mass spectrometry method for the determination of delta-aminolevulinic acid in plant leaves.
Hijaz F1, Killiny N2. J Chromatogr A. 2016 Apr 16. pii: S0021-9673(16)30464-2. doi: 10.1016/j.chroma.2016.04.041. [Epub ahead of print]
Delta-aminolevulinic (δ-ALA) acid is an important intermediate for tetrapyrroles biosynthesis and it has recently received great attention in plant physiology and human toxicology. However, the colorimetric method which is the most common method for determination of δ-ALA is time consuming and is not specific. In this study, a method for determination of δ-ALA in plant tissues was developed based on the trimethylsilyl (TMS) derivative of the pyrrole formed from the reaction of δ-ALA with ethyl acetoacetate via Knorr condensation. The δ-ALA in the HCl extract was reacted with ethyl acetoacetate to form a pyrrole. Then, the pyrrole compound was extracted using ethyl acetate and the solvent was evaporated to dryness. The dried sample was derivatized to its TMS ester and analyzed using GC-MS. The concentration of δ-ALA in citrus leaves incubated with levulinic acid was also determined by the conventional colorimetric method. The linear range was 10-200ppm in the full scan mode and 0.
4.Off-label photodynamic therapy for recalcitrant facial flat warts using topical 5-aminolevulinic acid.
Yang YL1,2, Sang J1,2, Liao NX1,2, Wei F1,2, Liao W1,2, Chen JH3,4. Lasers Med Sci. 2016 Apr 8. [Epub ahead of print]
The facial flat wart (verruca plana) is one of the most common reasons for dermatology and primary care visits. Although there are many therapeutic modalities, no single therapy has been proven to be completely curative. Case reports and uncontrolled studies suggested that photodynamic therapy (PDT) with topical 5-aminolevulinic acid (ALA) can effectively treat recalcitrant facial flat warts. A total of 12 patients with recalcitrant facial flat warts were enrolled in the study. ALA gel (10 %) was applied topically to lesions and incubated for 3 h. The lesions were irradiated by an LED light of 630 ± 10 nm at dose levels of 60-100 mW/cm. Clinical assessment was conducted before and after every treatment for up to 24 weeks. Among the ten patients completing three sessions of ALA-PDT, five had complete lesions clearance, and the other five patients were significantly improved. At the 24-week follow-up, the average effective rate was 88.8 %, with no recurrences.
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