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5-Aminolevulinic acid

CAS No.
106-60-5
Chemical Name:
5-Aminolevulinic acid
Synonyms
5-AMINOLEVULINATE;5-AMINOLAEVULINIC ACID;5-amino-4-oxovaleric acid;5-AMinelevulic acid (5-ALA);Kerastick;aminolevulinicacid;5-aminolevulinicaci;5-AMINOLEVULINIC ACID;AMINOLEVULINIC ACID, 5-;DELTA-AMINOLAEVULINICACID
CBNumber:
CB5265495
Molecular Formula:
C5H9NO3
Molecular Weight:
131.13
MDL Number:
MFCD00044485
MOL File:
106-60-5.mol
MSDS File:
SDS
Last updated:2023-09-05 17:53:06

5-Aminolevulinic acid Properties

Melting point 118-119 °C
Boiling point 242.42°C (rough estimate)
Density 1.3121 (rough estimate)
refractive index 1.4300 (estimate)
storage temp. 2-8°C(protect from light)
solubility Soluble in DMSO
pka 4.05(at 25℃)
CAS DataBase Reference 106-60-5(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 88755TAZ87
NCI Drug Dictionary aminolevulinic acid
ATC code L01XD04
EPA Substance Registry System Pentanoic acid, 5-amino-4-oxo- (106-60-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P261-P280-P305+P351+P338-P304+P340
HS Code  29225090

5-Aminolevulinic acid price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Matrix Scientific 089758 3,4-Bis(benzyloxy)benzaldehyde 95+% 106-60-5 1g $38 2021-12-16 Buy
ChemScene CS-W000450 5-Aminolevulinicacid 106-60-5 100mg $68 2021-12-16 Buy
Matrix Scientific 089758 3,4-Bis(benzyloxy)benzaldehyde 95+% 106-60-5 5g $101 2021-12-16 Buy
Matrix Scientific 089758 3,4-Bis(benzyloxy)benzaldehyde 95+% 106-60-5 10g $151 2021-12-16 Buy
American Custom Chemicals Corporation CHM0034621 5-AMINO LEVULINIC ACID 95.00% 106-60-5 50G $3722.25 2021-12-16 Buy
Product number Packaging Price Buy
089758 1g $38 Buy
CS-W000450 100mg $68 Buy
089758 5g $101 Buy
089758 10g $151 Buy
CHM0034621 50G $3722.25 Buy

5-Aminolevulinic acid Chemical Properties,Uses,Production

Description

5-aminolevulinic acid is the simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as a photosensitizing agent, an antineoplastic agent, a dermatologic drug, a prodrug, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a delta-amino acid and a 4-oxo monocarboxylic acid. It derives from a 4-oxopentanoic acid. It is a conjugate base of a 5-ammoniolevulinic acid. It is a conjugate acid of a 5-aminolevulinate. It is a tautomer of a 5-ammoniolevulinate.

Originator

Levulan Kerastick,DUSA Pharmaceuticals Inc.

Uses

5-Aminolevulinic acid (ALA), a nonprotein amino acid involved in tetrapyrrole synthesis, has been widely applied in agriculture, medicine, and food production.
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.

Indications

Aminolevulinic acid (ALA HCl, Levulan Kerastick) is indicated for the treatment of nonhyperkeratotic actinic keratosis of the face and scalp. It has two components, an alcohol solution vehicle and ALA HCl as a dry solid. The two are mixed prior to application to the skin. When applied to human skin, ALA is metabolized to protoporphyrin, which accumulates and on exposure to visible light produces a photodynamic reaction that generates reactive oxygen species (ROS).The ROS produce cytotoxic effects that may explain therapeutic efficacy. Local burning and stinging of treated areas of skin due to photosensitization can occur.

Definition

ChEBI: 5-aminolevulinic acid is the simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as a photosensitizing agent, an antineoplastic agent, a dermatologic drug, a prodrug, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a delta-amino acid and a 4-oxo monocarboxylic acid. It is functionally related to a 4-oxopentanoic acid. It is a conjugate base of a 5-ammoniolevulinic acid. It is a conjugate acid of a 5-aminolevulinate. It is a tautomer of a 5-ammoniolevulinate.

Manufacturing Process

1) Oxidation Step
2.27 g (10.0 mmol) of N-furfurylphthalimide was charged into a three-necked glass flask equipped with an oxygen feed tube, a thermometer, and a reflux condenser, and dissolved in 100 ml of anhydrous pyridine. After the addition of 7.0 mg of Rose Bengal, oxygen gas was fed at a rate of 20 ml/min at 10°- 20°C under irradiation by light. A 27 W white fluorescent lamp was used as a light source and the radiation was performed from the outside of the flask. After 7 hours, the irradiation was terminated and the pyridine was evaporated under reduced pressure to obtain 2.47 g of a light brown, semi-crystalline product.
2) Reduction Step (Hydrogenation)
2.00 g of the semi-crystalline solid obtained in (1) was dissolved in 40 ml of methanol and stirred at 50°C in a hydrogen atmosphere under atmospheric pressure in the presence of 200 mg of 5% palladium-on-carbon catalyst.
After five hours, the reaction was terminated and the mixture was allowed to cool to room temperature. The catalyst was removed by filtration and methanol was evaporated to obtain 2.11 g of white crystals.
The crystals were identified to be 5-phthalimidolevulinic acid by NMR analysis. The yield was 97%.
3) Hydrolysis Step
100 ml of 6 N hydrochloric acid was added to 2.11 g of the white crystals (2), and the mixture was heated under reflux for 5 hours.
After evaporating the hydrochloric acid under reduced pressure, a brown solid product was obtained and dissolved in ethanol. Acetone was added to the solution and the crystals produced were collected by filtration to obtain 0.689 g of 5-aminolevulinic acid hydrochloride. The yield based on Nfurfurylphthalimide was 51%.
NMR spectrum data conformed to 5-aminolevulinic acid hydrochloride

Therapeutic Function

Photosensitizer

Biological Activity

5-Aminolevulinic acid (5-ALA) is a precursor in the biosynthesis of porphyrins, including heme. The conversion of 5-ALA to protoporphyrins within tissues produces a photosensitive target that produces reactive oxygen species upon exposure to light.1 In this way, it is used in photodynamic therapy for a range of dermatological conditions, cancers, and other diseases. Also, 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.

Enzyme inhibitor

This key metabolic precursor (FW = 131.13 g/mol; CAS 106-60-5; pKa values = 4.05 and 8.90 at 25°C; Symbol: ALA), also known as daminolevulinic acid, is essential for the biosynthesis of metal ion-binding tetrapyrrole ring systems (porphyrins, chlorophylls, and cobalamins). In non-photosynthetic eukaryotes (animals, insects, fungi, protozoa, and alphaproteobacteria), d-aminolevulinic acid is produced by the enzyme ALA synthase, using glycine and succinyl CoA as substrates. In plants, algae, bacteria, and archaea, it is produced from glutamyl-tRNA and glutamate-1-semialdehyde. 5-Aminolevulinic acid inhibits (R)-3-amino-2- methylpropionate:pyruvate aminotransferase. ALA Phototherapy: Protoporphyrin IX, the immediate heme precursor is a highly effective tissue photosensitizer that is synthesized in four steps from 5- aminolevulinic acid. ALA synthesis is regulated via a feedback inhibition and gene repression mechanism linked to the concentration of free heme. In certain cell and tissue types, addition of exogenous ALA bypasses these regulation mechanisms, inducing uptake and synthesis of photosensitizing concentrations of Protoporphyrin IX, or PpIX. Topical application of ALA to certain malignant and non-malignant skin lesions, for example, can induce a clinically useful degree of lesion-specific photosensitization (e.g., superficial basal cell carcinomas show high response rate (~79%) after a single phototherapy treatment). ALA also induces localized tissue-specific photosensitization, when injected intradermally. In this sense, ALA and its methyl ester (methyl aminolevulinate, or MAL; trade name: Metvix?) are prodrugs that increase the amounts of the active drug (PpIX).

92632-81-0
106-60-5
Synthesis of 5-Aminolevulinic acid from 5-phthaliMidolevulinic acid

5-Aminolevulinic acid Preparation Products And Raw materials

Global( 210)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5990 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 14936 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9354 55
Biochempartner
0086-13720134139 candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282 alice@crovellbio.com China 8823 58
Changzhou Ditong Chemical Co.,Ltd
+86-0519-88299272 info@edengenechem.com China 2169 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
Alchem Pharmtech,Inc.
8485655694 sales@alchempharmtech.com United States 63711 58

View Lastest Price from 5-Aminolevulinic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
5-Aminolevulinic acid pictures 2023-09-05 5-Aminolevulinic acid
106-60-5
US $40.00 / kg 1kg 0.99 10 tons Hebei Yanxi Chemical Co., Ltd.
5-aminolevulinic acid ,5-ALA  pictures 2023-06-26 5-aminolevulinic acid ,5-ALA
106-60-5
US $150.00 / ASSAYS 10g >99% 500kg/month Hebei Mingeng Biotechnology Co., Ltd
5-Aminolevulinic acid//5-ALA pictures 2023-03-22 5-Aminolevulinic acid//5-ALA
106-60-5
US $1.00 / kg 1kg 99.6% 100tons Hebei Duling International Trade Co. LTD
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