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5-Aminolevulinic acid hydrochloride

SKU: A0364

Category: Metabolites

Synonyms: delta-Aminolevulinic acid hydrochloride , 5-Amino-4-oxopentanoic acid hydrochloride , 5-Aminolaevulinic acid hydrochloride , 5-ALA; 5451-09-2
CAS-Number: C₅H₉NO₃ . HCl
Molecular Formula: 131.13 . 36.46
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: DMSO (10mg/ml), methanol (10mg/ml), water (10mg/ml)
Melting Point: 144-151 °C

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Very hygroscopic. Store under inert gas.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Transportation: Not dangerous goods

Description: 5-Aminolevulinic acid (5-ALA) is a non-proteinogenic five carbon amino acid, which is the precursor for the biosynthesis of tetrapyrrole compounds, such as heme, chlorophyll and vitamin B12 and has broad applications in the medical and agricultural fields. The conversion of 5-ALA to protoporphyrins within tissues produces a photosensitive target that produces reactive oxygen species upon exposure to light. In this way, it is used in photodynamic therapy for a range of dermatological conditions, cancers, and other diseases. Oral administration of 5-ALA leads to the preferential accumulation of the fluorescent molecule protoporphyrin IX within certain types of cancer cells. This allows fluorescence-based identification of tumor tissue for accurate resection of diseased tissue. In addition to tumor therapy, 5-ALA has been implicated in the treatment of inflammatory disease, autoimmune disease and transplantation due to the anti-inflammation and immunoregulation properties that are elicited with the expression of heme oxygenase (HO)-1. ALA-based photodynamic therapy (PDT) has also a role in the treatment of microbial infections.
Smiles: [NH3+]CC(CCC(O)=O)=O.[Cl-]
InChi Key: ZLHFONARZHCSET-UHFFFAOYSA-N
References: (1) S.L. Marcus, et al., J. Clin. Laser Med. Surg. 14, 59 (1996) , (2) Q. Peng, et al., Photochem. Photobiol. 65, 235 (1997) , (3) S.A. Friesen, et al., Int. J. Oncol. 21, 577 (2002) , (4) M.C. Issa & M. Manela-Azulay, An. Bras. Dermatol. 85, 501 (2010) , (5) F. Harris & L. Pierpoint, Med. Res. Rev. 32, 1292 (2012) , (6) M. Fujino, et al., Int. Immunopharmacol. 37, 71 (2016) , (7) S.H. Halani & D.C. Adamson, Onco. Targets Ther. 9, 5629 (2016) , (8) M.O. Chohan & M.S. Berger, J. Neurooncol. (Epub ahead of print) (2018)
InChi: InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9 , /h1-3,6H2,(H,8,9) , 1H

5-Aminolevulinic acid (5-ALA) is a non-proteinogenic five carbon amino acid, which is the precursor for the biosynthesis of tetrapyrrole compounds, such as heme, chlorophyll and vitamin B12 and has broad applications in the medical and agricultural fields. The conversion of 5-ALA to protoporphyrins within tissues produces a photosensitive target that produces reactive oxygen species upon exposure to light. In this way, it is used in photodynamic therapy for a range of dermatological conditions, cancers, and other diseases. Oral administration of 5-ALA leads to the preferential accumulation of the fluorescent molecule protoporphyrin IX within certain types of cancer cells. This allows fluorescence-based identification of tumor tissue for accurate resection of diseased tissue. In addition to tumor therapy, 5-ALA has been implicated in the treatment of inflammatory disease, autoimmune disease and transplantation due to the anti-inflammation and immunoregulation properties that are elicited with the expression of heme oxygenase (HO)-1. ALA-based photodynamic therapy (PDT) has also a role in the treatment of microbial infections.

SKU: A0364 Category: Metabolites

Additional information

Additional information

Synonyms	delta-Aminolevulinic acid hydrochloride, 5-Amino-4-oxopentanoic acid hydrochloride, 5-Aminolaevulinic acid hydrochloride, 5-ALA
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	5451-09-2
Molecular Formula	C5H9NO3 . HCl
Molecular Weight	131.13 . 36.46
Identity	1H-NMR
Solvents	DMSO (10mg/ml), methanol (10mg/ml), water (10mg/ml)
Melting Point	144-151 °C
Smiles	[NH3+]CC(CCC(O)=O)=O.[Cl-]
InChi Key	ZLHFONARZHCSET-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Very hygroscopic. Store under inert gas.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Transportation	Not dangerous goods
References	(1) S.L. Marcus, et al., J. Clin. Laser Med. Surg. 14, 59 (1996), (2) Q. Peng, et al., Photochem. Photobiol. 65, 235 (1997), (3) S.A. Friesen, et al., Int. J. Oncol. 21, 577 (2002), (4) M.C. Issa & M. Manela-Azulay, An. Bras. Dermatol. 85, 501 (2010), (5) F. Harris & L. Pierpoint, Med. Res. Rev. 32, 1292 (2012), (6) M. Fujino, et al., Int. Immunopharmacol. 37, 71 (2016), (7) S.H. Halani & D.C. Adamson, Onco. Targets Ther. 9, 5629 (2016), (8) M.O. Chohan & M.S. Berger, J. Neurooncol. (Epub ahead of print) (2018)
InChi	InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9, /h1-3,6H2,(H,8,9), 1H
Quantity	500 mg, 1 g, Bulk