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5451-09-2

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5451-09-2 Usage

Chemical Properties

white to pale yellow crystals or

Uses

Different sources of media describe the Uses of 5451-09-2 differently. You can refer to the following data:
1. 5-Aminolevulinic acid hydrochloride finds an important role as a precursor in the synthesis of tetrapyrroles such as chlorophyll and heme. It is widely utilized in photodynamic therapy of diseases namely, Paget?s disease and human papillomavirus (HPV) infection-associated cervical condylomata acuminata.
2. Naturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer).
3. 5-Aminolevulinic acid hydrochloride has been used as a supplement for culturing Escherichia coli cells for heme biosynthesis.

Definition

ChEBI: A hydrochloride that is the monohydrochloride of 5-aminolevulinic acid. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used in combination with blue light illumination for the treatment of minimally to moderat ly thick actinic keratosis of the face or scalp.

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.

Purification Methods

Dry ALA-HCl in a vacuum desiccator over P2O5 overnight, then crystallise it by dissolving it in cold EtOH and adding dry Et2O. Also crystallis

Check Digit Verification of cas no

The CAS Registry Mumber 5451-09-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,5 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5451-09:
(6*5)+(5*4)+(4*5)+(3*1)+(2*0)+(1*9)=82
82 % 10 = 2
So 5451-09-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H

5451-09-2 Well-known Company Product Price

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  • TCI America

  • (A0325)  5-Aminolevulinic Acid Hydrochloride  >98.0%(T)

  • 5451-09-2

  • 100mg

  • 220.00CNY

  • Detail
  • TCI America

  • (A0325)  5-Aminolevulinic Acid Hydrochloride  >98.0%(T)

  • 5451-09-2

  • 1g

  • 995.00CNY

  • Detail
  • USP

  • (1025715)  Aminolevulinic acid hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 5451-09-2

  • 1025715-200MG

  • 4,647.24CNY

  • Detail
  • Sigma-Aldrich

  • (08339)  5-Aminolevulinic acid hydrochloride  ≥97.0% (AT)

  • 5451-09-2

  • 08339-1G

  • 1,288.17CNY

  • Detail
  • Sigma-Aldrich

  • (08339)  5-Aminolevulinic acid hydrochloride  ≥97.0% (AT)

  • 5451-09-2

  • 08339-5G

  • 4,557.15CNY

  • Detail

5451-09-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Aminolevulinic Acid Hydrochloride

1.2 Other means of identification

Product number -
Other names Pentanoic acid, 5-amino-4-oxo-, hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5451-09-2 SDS

5451-09-2Synthetic route

5-phthalimidyl levulinic acid
92632-81-0

5-phthalimidyl levulinic acid

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 6h; Reflux;96.6%
With hydrogenchloride In water for 10h; Reflux;85%
With hydrogenchloride In water for 16h; Reflux;83%
With hydrogenchloride for 8h; Heating;63.8%
N-acetyl-5-aminolevulinic acid methyl ester
93393-93-2

N-acetyl-5-aminolevulinic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 100℃;95%
ethyl 5-nitro-4-oxopentanoate

ethyl 5-nitro-4-oxopentanoate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; water; hydrogen; palladium on activated charcoal under 1137.73 Torr;94%
methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate
109258-71-1

methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 10h; Heating;92%
With hydrogenchloride 1.) water, reflux, 10 h, 2.) acetone, 60-70 deg C; Yield given. Multistep reaction;
With hydrogenchloride In water
With hydrogenchloride; water85 %Chromat.
benzoylaminolevulinic acid
102872-00-4

benzoylaminolevulinic acid

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 12h; Reflux;92%
C12H22N4O2

C12H22N4O2

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Stage #1: C12H22N4O2 With sodium hypochlorite; sodium hydroxide In water at 0℃; for 2h;
Stage #2: With hydrogenchloride In water for 0.5h; pH=1;
86.9%
C9H15NO5

C9H15NO5

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 100℃; Industrial scale;86.5%
dimethyl 2-(acetylamino)-3-oxohexanedioate
222641-36-3

dimethyl 2-(acetylamino)-3-oxohexanedioate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; water for 4h; Heating;85%
diethyl 2-acetylamino-3-oxohexanedioate
839724-53-7

diethyl 2-acetylamino-3-oxohexanedioate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate for 4h; Heating / reflux;82%
methyl 5-nitro-4-oxopentanoate

methyl 5-nitro-4-oxopentanoate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; zinc In water at 110℃; for 45h; Reagent/catalyst; Temperature;80%
5,5-dimethoxy-2-oxopiperidine-1-carboxylic acid methyl ester
155585-41-4

5,5-dimethoxy-2-oxopiperidine-1-carboxylic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 12h; Heating;77%
methyl 5-azidolevulinate
159150-70-6

methyl 5-azidolevulinate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 2h; Ambient temperature;75%
5-(azidomethyl)furan-2-carbaldehyde
1268257-14-2

5-(azidomethyl)furan-2-carbaldehyde

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Stage #1: 5-(azidomethyl)furan-2-carbaldehyde With oxygen; rose bengal In methanol at 20℃; for 6h; UV-irradiation;
Stage #2: With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol under 1520.1 Torr; for 6h;
74%
methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate
109258-71-1

methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate

A

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 12℃; Heating;A 73.2%
B n/a
5-(acetylamino)-6-ethoxy-4,6-dioxohexanoic acid
652151-56-9

5-(acetylamino)-6-ethoxy-4,6-dioxohexanoic acid

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
In hydrogenchloride Heating;73%
4-oxo-5-acetylaminopentanoic acid
20238-92-0

4-oxo-5-acetylaminopentanoic acid

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Heating;70%
With hydrogenchloride
With hydrogenchloride In water at 115℃; for 1h; Temperature;
5-Aminomethyl-dihydro-furan-2-one; hydrochloride

5-Aminomethyl-dihydro-furan-2-one; hydrochloride

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid 1.) reflux, 4 h, 2.) r.t., overnight;65%
piperidine-2,5-dione
52065-78-8

piperidine-2,5-dione

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 12h; Heating;51%
2,2-dimethyl-4,6-dioxo-5-(3-phthalimido-2-oxopropyl)-1,3-dioxane
114681-18-4

2,2-dimethyl-4,6-dioxo-5-(3-phthalimido-2-oxopropyl)-1,3-dioxane

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride 1.) water, reflux, 10 h, 2.) acetone, 60-70 deg C; Yield given. Multistep reaction;
tert-butyl methylether

tert-butyl methylether

5-azido levulinic acid

5-azido levulinic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
In hydrogenchloride; methanol; hydrogen
5-(azidomethyl)dihydrofuran-2(3H)-one
179532-81-1

5-(azidomethyl)dihydrofuran-2(3H)-one

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / Raney nickel / diethyl ether; H2O / 0.33 h / Ambient temperature
2: 65 percent / CrO3, 5percent aq. H2SO4 / 1.) reflux, 4 h, 2.) r.t., overnight
View Scheme
methyl 5-bromo-4-oxopentanoate
53856-93-2

methyl 5-bromo-4-oxopentanoate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / NaN3 / dimethylformamide / 1 h / -10 °C
2: 75 percent / H2, HCl / 30percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 59 percent / dimethylformamide / 1 h / Ambient temperature
2: 92 percent / 6 M HCl / 10 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) DMFA, 20 deg C, 20 min, 2.) 72 h, 3.) water, 20 deg C, 24 h
2: 1.) conc. HCl, 2.) conc. HCl / 1.) water, reflux, 10 h, 2.) acetone, 60-70 deg C
View Scheme
levulinic acid
123-76-2

levulinic acid

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Br2 / 3.5 h / Heating
2: 100 percent / NaN3 / dimethylformamide / 1 h / -10 °C
3: 75 percent / H2, HCl / 30percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: bromine / 22 - 23 °C / Large scale
2: N,N-dimethyl-formamide
3: hydrogenchloride / water
View Scheme
3-oxopiperidine-1-carboxylic acid methyl ester
61995-18-4

3-oxopiperidine-1-carboxylic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / 0.5 h
2: 62 percent / NaIO4, RuO2 / ethyl acetate; H2O / 18 h / Ambient temperature
3: 77 percent / 7 M aq. HCl / ethanol / 12 h / Heating
View Scheme
3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester
56475-87-7

3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) CH3COOK, 3.) aq. Na2CO3 / 1.) electrolysis, electrochemical oxidation
2: 84 percent / p-toluenesulfonic acid / 0.5 h
3: 62 percent / NaIO4, RuO2 / ethyl acetate; H2O / 18 h / Ambient temperature
4: 77 percent / 7 M aq. HCl / ethanol / 12 h / Heating
View Scheme
3,3-dimethoxypiperidine-1-carboxylic acid methyl ester
155585-40-3

3,3-dimethoxypiperidine-1-carboxylic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / NaIO4, RuO2 / ethyl acetate; H2O / 18 h / Ambient temperature
2: 77 percent / 7 M aq. HCl / ethanol / 12 h / Heating
View Scheme
5-Acetoxy-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester

5-Acetoxy-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / aq. Na2CO3 / methanol / 0.33 h / Ambient temperature
2: 84 percent / p-toluenesulfonic acid / 0.5 h
3: 62 percent / NaIO4, RuO2 / ethyl acetate; H2O / 18 h / Ambient temperature
4: 77 percent / 7 M aq. HCl / ethanol / 12 h / Heating
View Scheme
2-Pyridone
142-08-5

2-Pyridone

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 34 percent / Elbs oxidation
2: 76 percent / H2 / Pd/C / methanol / 5 h / 30 °C
3: 51 percent / conc. HCl / 12 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 34 percent / Elbs oxidation
2: 54 percent / KOH / dimethylsulfoxide / 1 h
3: H2 / Pd/C / methanol / 3 h / 30 °C
4: 51 percent / conc. HCl / 12 h / Heating
View Scheme
2,5-dihydroxypyridine
5154-01-8

2,5-dihydroxypyridine

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / H2 / Pd/C / methanol / 5 h / 30 °C
2: 51 percent / conc. HCl / 12 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 54 percent / KOH / dimethylsulfoxide / 1 h
2: H2 / Pd/C / methanol / 3 h / 30 °C
3: 51 percent / conc. HCl / 12 h / Heating
View Scheme
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

silver methanesulfonate
2386-52-9

silver methanesulfonate

5-amino-4-oxopentanoic acid methanesulfonate

5-amino-4-oxopentanoic acid methanesulfonate

Conditions
ConditionsYield
In water96%
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

2,5-(β-carboxyethyl)dihydropyrazine
77479-03-9

2,5-(β-carboxyethyl)dihydropyrazine

Conditions
ConditionsYield
With nitrogen In sodium hydroxide Cyclization;95%
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

5-aminolevulinic acid phosphate

5-aminolevulinic acid phosphate

Conditions
ConditionsYield
With phosphoric acid; triethylamine In water at 0 - 20℃; for 0.166667h; Product distribution / selectivity;93%
With phosphoric acid; triethylamine In ethanol; water at 0 - 20℃; for 1h; Product distribution / selectivity;90%
With picoline; phosphoric acid In water at 20℃; for 0.166667h; Product distribution / selectivity;77%
monoethyl ether of triethylene glycol
112-50-5

monoethyl ether of triethylene glycol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

5-amino-4-oxo-pentanoic acid 2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethyl ester; hydrochloride

5-amino-4-oxo-pentanoic acid 2-[2-(2-ethoxy-ethoxy)-ethoxy]-ethyl ester; hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 5h;90%
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

2-Methoxyethyl 5-amino-4-oxopentanoate Hydrochloride

2-Methoxyethyl 5-amino-4-oxopentanoate Hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 5h;90%
With thionyl chloride at 60℃; for 5h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

5-((tert-butoxycarbonyl)amino)-4-oxopentanoic acid
72072-06-1

5-((tert-butoxycarbonyl)amino)-4-oxopentanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol at 21℃; Inert atmosphere;90%
With sodium hydrogencarbonate In methanol at 20℃; for 12h;90%
With sodium hydrogencarbonate In methanol for 6h; Inert atmosphere; Sonication;82%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Cooling with ice;78%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 18h; pH=8.5;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

5-amino-4-oxo-pentanoic acid 2-ethoxy-ethyl ester; hydrochloride

5-amino-4-oxo-pentanoic acid 2-ethoxy-ethyl ester; hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 5h;89%
With thionyl chloride at 60℃; for 5h;
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

5-hexenyl 5-aminolevulinate hydrochloride

5-hexenyl 5-aminolevulinate hydrochloride

Conditions
ConditionsYield
Stage #1: 5-aminolevulinic acid hydrochloride With thionyl chloride; N,N-dimethyl-formamide
Stage #2: 5-Hexen-1-ol at 20℃; for 1.5h;
89%
ethoxyethoxyethanol
111-90-0

ethoxyethoxyethanol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

3,6-Dioxa-1-octyl 5-amino-4-oxopentanoate Hydrochloride

3,6-Dioxa-1-octyl 5-amino-4-oxopentanoate Hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 5h;87%
0.90 g (53%)
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid
218129-12-5

3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Conditions
ConditionsYield
With sodium acetate In water at 100℃; for 16h; Knorr pyrrole synthesis;87%
With sodium acetate In water at 100℃; for 16h;82%
With sodium acetate In water at 110℃; for 12h;60%
With sodium acetate In water at 110℃; for 12h; Product distribution / selectivity;
methanol
67-56-1

methanol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

methyl aminolevulinate
79416-27-6

methyl aminolevulinate

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 30h;86.3%
With thionyl chloride at 20℃; for 48h;81%
With thionyl chloride at 0 - 20℃;
With thionyl chloride
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

hexan-1-ol
111-27-3

hexan-1-ol

5-amino-4-oxo-pentanoic acid hexyl ester; hydrochloride

5-amino-4-oxo-pentanoic acid hexyl ester; hydrochloride

Conditions
ConditionsYield
Stage #1: hexan-1-ol With thionyl chloride at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 5-aminolevulinic acid hydrochloride at 20℃; for 3h; Inert atmosphere; Reflux;
86%
With thionyl chloride for 26h; Heating;48.2%
With thionyl chloride at 60℃; for 5h;
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

hexan-1-ol
111-27-3

hexan-1-ol

5-aminolaevulinic acid n-hexyl ester

5-aminolaevulinic acid n-hexyl ester

Conditions
ConditionsYield
Stage #1: 5-aminolevulinic acid hydrochloride; hexan-1-ol With thionyl chloride for 0.166667h; Cooling with ice;
Stage #2: 5-aminolevulinic acid hydrochloride at 20 - 80℃; for 3h; Heating;
86%
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

acetylacetone
123-54-6

acetylacetone

3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid
38664-17-4

3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid

Conditions
ConditionsYield
With sodium acetate In water at 100℃; for 16h; Knorr pyrrole synthesis;85%
cycloheptane-1,3-dione
1194-18-9

cycloheptane-1,3-dione

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

3-(4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-3-yl)propanoic acid
760998-19-4

3-(4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-3-yl)propanoic acid

Conditions
ConditionsYield
With sodium acetate In water at 100℃; for 2h;80%
With sodium acetate In water at 100℃; for 16h; Knorr pyrrole synthesis;75%
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

butan-1-ol
71-36-3

butan-1-ol

5-aminolevulinic acid butyl ester hydrochloride

5-aminolevulinic acid butyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 0.416667h; Heating;78.9%
homoalylic alcohol
627-27-0

homoalylic alcohol

5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

3-butenyl 5-aminolevulinate hydrochloride

3-butenyl 5-aminolevulinate hydrochloride

Conditions
ConditionsYield
Stage #1: 5-aminolevulinic acid hydrochloride With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 12h;
Stage #2: homoalylic alcohol at 20℃; for 1.5h;
77%
5-aminolevulinic acid hydrochloride
5451-09-2

5-aminolevulinic acid hydrochloride

dimedone
126-81-8

dimedone

3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid
258831-35-5

3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Conditions
ConditionsYield
With sodium acetate In water at 100℃; for 16h; Knorr pyrrole synthesis;76%
With sodium acetate In water at 110℃; for 4h;68%
With sodium acetate In water at 110℃; for 4h;68%

5451-09-2Relevant articles and documents

Convenient syntheses of δ-aminolevulinic acid

Nudelman, Ayelet,Nudelman, Abraham

, p. 568 - 570 (1999)

Two convenient procedures for the synthesis of δ-aminolevulinic acid (5-ALA) are described.

A convenient method for introducing oxo group into the β-position of cyclic amines and its application to synthesis of δ-aminolevulinic acid

Matsumura,Takeshima,Okita

, p. 304 - 306 (1994)

Oxo group could be introduced into the β-position of N-methoxycarbonylated cyclic amines by utilizing electrochemical oxidation and/or m-chloroperbenzoic acid oxidation, and this method was applied to the preparation of δ-aminolevulinic acid, an intermediate of chlorophyll biosynthesis.

Preparation method 5 - ALA intermediate 5 - bromoolevulinic acid ester

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Paragraph 0034; 0053; 0057, (2021/09/22)

The invention relates to a preparation method of 5 - ALA intermediate 5 - bromoacetyl ester, which is characterized by comprising the following steps: (S1) reaction of the urotropine and a bromine source to prepare the urotropine bromine complex. (S2) Lourotropine bromide complex and levulinic acid ester reaction. Gave 5 - bromoolevulinic acid ester. Compared with the prior art, a bromo reagent such as liquid bromine and 5 - is used directly, NBS-site bromination product yield is increased 5 - 10% or more. The defect that 3 -position bromination or multi-site bromination product is large and separation is difficult in the bromination reaction is overcome. The method is cheap and easily available in raw materials, simple and convenient to operate and suitable for large-scale preparation 5 - ALA intermediate 5 - bromolevulinic acid ester .

Preparation method of 5-aminolevulinic acid hydrochloride

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Paragraph 0043; 0049-0050, (2021/11/06)

The invention discloses a preparation method of 5-aminolevulinic acid hydrochloride, the method comprises the following steps: taking 1, 3-dichloroacetone as an initial raw material, reacting with a malonate compound, then carrying out ammonification reaction and hydrolysis decarboxylation, and finally decolorizing, concentrating and recrystallizing to obtain the 5-aminolevulinic acid hydrochloride. The method is high in yield, convenient to operate, stable in quality and suitable for large-scale industrial production.

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