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08339

Sigma-Aldrich

5-Aminolevulinic acid hydrochloride

≥97.0% (AT)

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/REAXYS Number:
3690651
EC Number:
226-679-5
MDL number:
MFCD00012869
UNSPSC Code:
12352209
PubChem Substance ID:
329748570
NACRES:
NA.26

Quality Level

200

assay

≥97.0% (AT)

form

powder or crystals

impurities

≤2% water

color

white to faint yellow

mp

~150 °C (dec.)

application(s)

peptide synthesis

storage temp.

2-8°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 as a supplement for culturing Escherichia coli cells for heme biosynthesis.

Biochem/physiol Actions

5-Aminolevulinic acid (5-ALA) may interact with several transporters such as glutamate, γ-aminobutyric acid (GABA), di-, tri-peptides, and organic transporters in the blood-brain barrier. It may also act as a precursor for the synthesis of porphyrins in chlorophyll and hemes. 5-ALA exhibits plant growth regulator activities.
Intermediate in heme biosynthesis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK2745
BCCG8728
BCCC9212
BCCB1809
BCBZ9449

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5-Aminolevulinic acid and the blood-brain barrier-A review
Novotny A, et al.
Medical Laser Application, 18(1), 36-40 (2003)
Zhimin Yang et al.
PloS one, 9(12), e116283-e116283 (2015-01-01)
The objectives of this study were to determine whether foliar application of a chlorophyll precursor, 5-aminolevulinic acid (ALA), could mitigate salinity stress damages in perennial grass species by regulating photosynthetic activities, ion content, antioxidant metabolism, or metabolite accumulation. A salinity-sensitive
N Neittaanmäki-Perttu et al.
The British journal of dermatology, 171(5), 1172-1180 (2014-08-12)
Daylight-mediated photodynamic therapy (DL-PDT) using methyl-5-aminolaevulinate (MAL) is effective for thin, grade I, actinic keratoses (AK). There are no published studies of other photosensitizers used in DL-PDT. To compare the efficacy and adverse effects of 5-aminolaevulinic acid nanoemulsion (BF-200 ALA)
Giovanni Pagano et al.
International journal of molecular sciences, 15(11), 20169-20208 (2014-11-08)
An extensive number of pathologies are associated with mitochondrial dysfunction (MDF) and oxidative stress (OS). Thus, mitochondrial cofactors termed "mitochondrial nutrients" (MN), such as α-lipoic acid (ALA), Coenzyme Q10 (CoQ10), and l-carnitine (CARN) (or its derivatives) have been tested in
Anupam Patgiri et al.
Nature biotechnology, 38(3), 309-313 (2020-01-15)
An elevated intracellular NADH:NAD+ ratio, or 'reductive stress', has been associated with multiple diseases, including disorders of the mitochondrial electron transport chain. As the intracellular NADH:NAD+ ratio can be in near equilibrium with the circulating lactate:pyruvate ratio, we hypothesized that
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