5-amino-4-oxopentanoic acid hydrochloride

• ChemBase ID: 68223
• Molecular Formular: C5H10ClNO3
• Molecular Mass: 167.5908
• Monoisotopic Mass: 167.03492087
• SMILES: C(=O)(CCC(=O)CN)O.Cl
• Canonical SMILES: NCC(=O)CCC(=O)O.Cl
• InChI: InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H
• InChIKey: ZLHFONARZHCSET-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-4-oxopentanoic acid hydrochloride
• IUPAC Traditional name: aminolevulinic acid hydrochloride
• Synonyms: 5-Aminolevulinic acid hydrochloride; 5-Aminolevulinic acid hydrochloride; 5-Amino-4-oxovaleric acid hydrochloride; 5-Amino-4-oxopentanoic acid hydrochloride 98%; δ-Aminolevulinic acid hydrochloride; 5-Aminolaevulinic acid hydrochloride; 5-Aminolevulinic acid hydrochloride; 5-Amino-4-ketovaleric acid hydrochloride; Aminolevulinic Acid Hydrochloride; 5-ALA HCl; 5-Aminolevulinic Acid Hydrochloride Salt; 5-Aminolevulinic acid; 5-Amino-4-oxopentanoic acid hydrochloride; delta-AMINOLEVULINIC ACID HYDROCHLORIDE; Levulan; ALA; 5-Amino-4-oxopentanoic acid hydrochloride; 5-氨基酮戊酸盐酸盐

Database IDs

• CAS Number: 5451-09-2; 5451-09-2
• EC Number: 226-679-5
• MDL Number: MFCD00012869
• Beilstein Number: 3690651
• Merck Index: 14446
• PubChem SID: 24890811; 24891281; 162033955; 24846161
• PubChem CID: 123608

CALCULATED PROPERTIES

• Acid pKa: 4.0531516
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.2572048
• LogD (pH = 7.4): -3.3702924
• Log P: -3.2526455
• Molar Refractivity: 30.4478 cm^3
• Polarizability: 12.14889 Å^3
• Polar Surface Area: 80.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble50 mg/mL; Methanol; Water
• Apperance: powder; White Solid
• Melting Point: ~150 °C (dec.); 149-153°C; 156°C (Decomposes); 156-158(dec.)°C; ca 156^ dec.

Safety Information

• Storage Condition: 0°C; -20°C; -20°C Freezer
• Storage Warning: Hygroscopic; IRRITANT; Irritant/Hygroscopic/Keep Cold/Store under Argon
• RTECS: OI1640000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: -; 3
• Risk Statements: 36/38
• Safety Statements: 26
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~98%; ≥97.0% (AT); ≥98%; 95+%; 97%; 98%; 99%
• Grade: purum
• Salt Data: hydrochloride
• Suitability: suitable for cell culture
• Impurities: ≤2% water
• Quality Level: PREMIUM
• Linear Formula: NH2CH2C(O)CH2CH2COOH · HCl

DETAILS

MP Biomedicals - 02100247

Purity: Approx. 98%
Hydrochloride

Selleck Chemicals - S2553

Research Area: Cancer
Biological Activity:
5-Aminolevulinic acid is an intermediate in heme biosynthesis in the body and the universal precursor of tetrapyrroles, such as chlorophyll and heme. In mammals, yeast, fungi and the purple bacteria, 5-aminolevulinic acid is formed by the Shemin pathway. Then it is used in the synthesis of hemes, vitamin B12 and bacteriochlorophyll. Two molecules of 5-aminolevulinic acid are condensed to form porphobilinogen. It is the first step compound in the porphyrin synthesis. Aminolevulinic acid HCl (5-aminolevulinic acid HCl) is a prodrug that is metabolized intracellularly to form the photosensitizing molecule protoporphyrin (PpIX). When PpIX is activated by light, cytotoxic reactive oxygen species and free radicals are generated. ALA can diffuse through skin and preferentially localizes in tumors and dysplasic tissue. Subsequent exposure of PpIX-loaded tumor cells to light can destroy the tumor. [1][2]

Sigma Aldrich - A7793

Biochem/physiol Actions
Intermediate in heme biosynthesis.
包装
10 mg in autosmp vl
Application
5-Aminolevulinic acid formed from glycine and succinyl CoA by ALA synthase is the first compound in prophyrin biosynthesis pathway. 5-Aminolevulinic acid is used in photodynamic therapy. This compound may be used to study the effects of photodynamic therapy in vitro.

Sigma Aldrich - A3785

Biochem/physiol Actions
Intermediate in heme biosynthesis.
包装
1, 5 g in glass bottle
500 mg in glass bottle

Sigma Aldrich - 08339

Biochem/physiol Actions
Intermediate in heme biosynthesis.

Toronto Research Chemicals - A611780

Naturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer).

REFERENCES

• gura S et al. BMC Res Notes. 2011 Mar 17; 4:66.
• Sisler, E.C., et al.: Physiol. Plant., 16, 315 (1963)
• Herdeis, C., et al.: Arch. Pharm., 317, 304 (1963)
• Peng, Q., et al.: Cancer, 79, 2282(1963)