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A3785

Sigma-Aldrich

5-Aminolevulinic acid hydrochloride

≥98%

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Synonym(s):
δ-Aminolevulinic acid hydrochloride, 5-Amino-4-oxopentanoic acid hydrochloride, 5-Aminolaevulinic acid hydrochloride, ALA
Linear Formula:
NH2CH2C(O)CH2CH2COOH · HCl
CAS Number:
5451-09-2
Molecular Weight:
167.59
Beilstein:
3690651
EC Number:
226-679-5
MDL number:
MFCD00012869
PubChem Substance ID:
24890811
NACRES:
NA.26

Quality Level

300

Assay

≥98%

form

powder

technique(s)

ligand binding assay: suitable

mp

150 °C

storage temp.

−20°C

SMILES string

Cl[H].NCC(=O)CCC(O)=O

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

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Application

5-Aminolevulinic acid hydrochloride has been used to activate or inhibit heme biosynthesis in HeLa and K562 cell lines. It has also been used in photodynamic therapy for A431 tumor bearing mice.

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.
Intermediate in heme biosynthesis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

农药列管产品

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Carla S Santos et al.
Plants (Basel, Switzerland), 8(9) (2019-09-22)
Iron deficiency chlorosis (IDC) is an abiotic stress often experienced by soybean, owing to the low solubility of iron in alkaline soils. Here, soybean lines with contrasting Fe efficiencies were analyzed to test the hypothesis that the Fe efficiency trait
Shigeru Kato et al.
The Journal of surgical research, 176(2), 430-436 (2012-01-10)
Lymph node metastasis is one of the most critical prognostic factors in patients with colorectal cancer. Although regional lymph nodes should be surgically resected and pathologically examined, techniques for the intraoperative diagnosis of lymph node metastasis remain to be well
Breann L Brown et al.
Structure (London, England : 1993), 26(4), 580-589 (2018-03-20)
5-Aminolevulinic acid synthase (ALAS) catalyzes the first step in heme biosynthesis. We present the crystal structure of a eukaryotic ALAS from Saccharomyces cerevisiae. In this homodimeric structure, one ALAS subunit contains covalently bound cofactor, pyridoxal 5'-phosphate (PLP), whereas the second
Francesca Bertino et al.
Pain, 160(12), 2766-2775 (2019-08-14)
Hereditary sensory and autonomic neuropathies (HSANs) are a group of clinically and genetically heterogeneous disorders of the peripheral nervous system mainly characterized by impaired nociception and autonomic dysfunction. We previously identified heme metabolism as a novel pathway contributing to sensory
Optimization of the heme biosynthesis pathway for the production of 5-aminolevulinic acid in Escherichia coli
Junli Zhang
Scientific Reports, 5 (2015)
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