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A3785

Sigma-Aldrich

5-Aminolevulinic acid hydrochloride

≥98%

Synonym(s):

δ-Aminolevulinic acid hydrochloride, 5-Amino-4-oxopentanoic acid hydrochloride, 5-Aminolaevulinic acid hydrochloride, ALA

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About This Item

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
UNSPSC Code:
12352209
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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USP

USP

1025726

Aminolevulinic acid Related Compound A

USP

USP

1025737

Aminolevulinic acid Related Compound B

4,6-Dioxoheptanoic acid powder

Sigma-Aldrich

D1415

4,6-Dioxoheptanoic acid

Protoporphyrin IX ≥95%

Sigma-Aldrich

P8293

Protoporphyrin IX

Temoporfin ≥90% (HPLC)

Sigma-Aldrich

SML1707

Temoporfin

Optimization of the heme biosynthesis pathway for the production of 5-aminolevulinic acid in Escherichia coli
Junli Zhang
Scientific Reports, 5 (2015)
Treatment of HPV infection-associated cervical condylomata acuminata with 5-aminolevulinic acid-mediated photodynamic therapy.
Wang HW
Photochemistry and Photobiology, 88(3), 565-569 (2012)
ALA-PpIX variability quantitatively imaged in A431
epidermoid tumors using in vivo ultrasoundfluorescence
tomography and ex vivo assay
Alisha V DSouza
SPIE Proc., 8931 null
The mitochondrial heme exporter FLVCR1b mediates erythroid differentiation
Deborah Chiabrando, et.al
The Journal of Clinical Investigation, 122(12), 4569-4579 (2012)
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
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