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22839-47-0

Basic Information
CAS No.: 22839-47-0
Name: Aspartame
Molecular Structure:
Molecular Structure of 22839-47-0 (Aspartame)
Formula: C14H18N2O5
Molecular Weight: 294.34
Synonyms: r-Sweet;(3S)-3-amino-3-[[(1S)-1-methoxycarbonyl-2-phenyl-ethyl]carbamoyl]propanoic acid;Sweet cornSweet dipeptide;(3S)-3-azaniumyl-3-[[(1S)-1-methoxycarbonyl-2-phenyl-ethyl]carbamoyl]propanoate;NutraSweet;H-Asp-Phe-OMe;3-amino-3-[(1-methoxycarbonyl-2-phenyl-ethyl)carbamoyl]propanoic acid;L-Phenylalanine,L-R-aspartyl-,2-methyl ester;Aspartame (USAN);Aspartame FCC 4;Succinamic acid, 3-amino-N-(alpha-carboxyphenethyl)-,N-methyl ester;Aspartame FCC4;Aspartame Granula;β-Aspartame;
EINECS: 245-261-3
Density: 1.28 g/cm3
Melting Point: 242-248 °C
Boiling Point: 535.8 °C at 760 mmHg
Flash Point: 277.8 °C
Solubility: Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
Appearance: White powder or tablets
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 118.72000
LogP: 0.78010
Synthetic route
27446-39-5

N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen fluoride; methoxybenzene at 0℃; for 0.5h;98%
33605-72-0

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal97%
With hydrogen; palladium
140233-83-6

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-(2-p-tolyl-acetylamino)-succinamic acid

A

622-47-9

4-tolylacetic acid

B

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 3.8h; Rate constant; Product distribution;A n/a
B 90%
101623-22-7

N-phenacetyl-α-L-aspartyl-L-phenylalanine methyl ester

A

103-82-2

phenylacetic acid

B

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With pH 7.5; penicillinacylase on Eupergit C beads In water at 28℃;A n/a
B 87%
With penicillin amidase at 25℃; for 2.5h;A n/a
B 99 % Chromat.
With penicillin amidase at 25℃; for 2.5h; Rate constant; Product distribution;A n/a
B 99 % Chromat.
5910-52-1

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; for 0.5h; pH=5;84%
With sodium carbonate In water pH=5.2;40%
40944-73-8

methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h;83%
With TFA-anisole
33605-76-4

N-formylaspartame

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol83%
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

131021-87-9

<(4S)-2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidine-4-yl>acetate

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;72%
In diethyl ether; ethyl acetate Ambient temperature;
4N-hydrochloric acid

4N-hydrochloric acid

33605-76-4

N-formylaspartame

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In water; tert-butyl alcohol70%

(S)-3-Formylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Heating;65%
41567-23-1

anhydride du N-chloroacetyl-L-acide aspartique

2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

A

22839-47-0

L-Asp-L-Phe-OMe

B

5910-52-1

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; thiourea; sodium chloride In methanol; 1,1-dichloroethane; waterA n/a
B 48%
140233-85-8

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-nitro-phenyl)-acetylamino]-succinamic acid

A

104-03-0

4-nitrobenzeneacetic acid

B

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 8.3h; Rate constant; Product distribution;A n/a
B 30%
104413-44-7

L-aspartic anhydride hydrochloride

75-93-4

methyl bisulfate

2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With sulfuric acid In methanol; 1,2-dichloro-ethane21.9%
104413-44-7

L-aspartic anhydride hydrochloride

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
21.8%
116147-62-7

n-formyl-l-aspartic anhydride

2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With potassium hydroxide; hydroxylamine hydrochloride In methanol; ethyl acetate21%
104413-44-7

L-aspartic anhydride hydrochloride

2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In methanol; 1,2-dichloro-ethane19.2%
4976-94-7

Boc-Asp(OtBu)-Phe-OMe

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With trifluoroacetic acid
5262-07-7

Z-Asp(OBzl)-Phe-OMe

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol
With hydrogen; palladium on activated charcoal
With palladium on carbon; hydrogen In methanol for 4h;
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

77217-04-0, 82522-65-4

L-aspartic acid N-thiocarboxyanhydride

A

22839-47-0

L-Asp-L-Phe-OMe

B

25548-16-7

aspartame

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) water, 0-5 deg C, pH 8.5-9.5, 2.) MeOH, water, 0 deg C, pH 4.5-5; Yield given. Multistep reaction. Yields of byproduct given;
125507-05-3, 125507-06-4

(S)-2-[(2-Benzyl-5-oxo-isoxazolidine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

A

22839-47-0

L-Asp-L-Phe-OMe

B

22839-66-3

(R)-Asp-(S)-PhOMe

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; water at 20℃; under 760 Torr; for 5h; Yield given. Yields of byproduct given;
With hydrogen; palladium dihydroxide In ethanol; water at 20℃; under 1 Torr; for 5h; Yield given. Yields of byproduct given;
125507-07-5, 125590-57-0, 125590-58-1

(S)-2-{[(S)-5-Oxo-2-((R)-1-phenyl-ethyl)-isoxazolidine-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; water at 70℃; under 760 Torr; for 5h;65 mg
140233-84-7

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-methoxy-phenyl)-acetylamino]-succinamic acid

A

104-01-8

4-Methoxyphenylacetic acid

B

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 7h; Product distribution; Rate constant;A n/a
B 92 % Chromat.

(S)-3-Benzyloxycarbonylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal Yield given;

aspartame hemihydrate, form I, ball-milled

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
at 130℃; Kinetics;
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 2 h / Ambient temperature
2: H2 / Pd
View Scheme
Multi-step reaction with 2 steps
1: 1.) pyridine, triethylamine, pivaloyl chloride; 2.) DMFA, 1-hydroxybenzotriazole / 1.) THF, 20 min, -10 deg C; 2.) CHCl3, 1.5 h 20 deg C
2: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: 1.) pyridine, triethylamine, pivaloyl chloride; 2.) DMFA, 1-hydroxybenzotriazole / 1.) THF; 2.) CHCl3
2: hydrogen / Pd/C / acetic acid
3: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
104413-52-7

L,L-N-t-Boc-Asp(OBz)-PM

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / Pd/C / acetic acid
2: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 66 percent / H2 / Pd / methanol; acetic acid / 3 h
2: TFA-anisole
View Scheme
22839-47-0

L-Asp-L-Phe-OMe

5241-71-4

Asp-Phe-NH2

Conditions
ConditionsYield
With ammonia at -40℃; for 10.25h;97%
24424-99-5

di-tert-butyl dicarbonate

22839-47-0

L-Asp-L-Phe-OMe

A

222641-22-7

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine methyl ester mono(sodium) salt

B

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine mono(sodium) salt

Conditions
ConditionsYield
With sodium hydroxide In methanol; water; ethyl acetateA n/a
B 97%

dichloro(p-cymene)ruthenium(II) dimer

22839-47-0

L-Asp-L-Phe-OMe

124-41-4

sodium methylate

{(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester)}Cl

Conditions
ConditionsYield
In methanol byproducts: NaCl; under Ar, addn. of 2 equivalents NaOMe-soln. to Ru-compd. and 2 equivalents of ligand in methanol, stirred for 30 min at room temp.; evapd. in vac., residue taken up in CH2Cl2, centrifuge (NaCl), dropwise addn. to pentane; elem. anal.;97%
22839-47-0

L-Asp-L-Phe-OMe

((L)-α-aspartyl)-(L)-phenylalaninamide ammonium salt

Conditions
ConditionsYield
With ammonia at -40℃; for 1.5h;95%
22839-47-0

L-Asp-L-Phe-OMe

5262-10-2

[(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid

Conditions
ConditionsYield
at 200℃; for 0.333333h;92%
In dimethyl sulfoxide at 80℃; for 8h;88%
at 180℃; Kinetics;
67-56-1

methanol

22839-47-0

L-Asp-L-Phe-OMe

N-α-L-aspartyl-L-phenylalanine dimethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 25℃; Schlenk technique; Inert atmosphere;91%
4013-72-3

nicotinoyl azide

22839-47-0

L-Asp-L-Phe-OMe

Nα-nicotinoyl-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 3h;90%

(2R, 4R)-monatin sodium salt

22839-47-0

L-Asp-L-Phe-OMe

mixed crystals (salt) of (2R,4R)-monatin and aspartame

mixed crystals (salt) of (2R,4R)-monatin and aspartame

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 0.166667h;87.2%

dichloro(p-cymene)ruthenium(II) dimer

22839-47-0

L-Asp-L-Phe-OMe

124-41-4

sodium methylate

(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester(2-))*H2O

Conditions
ConditionsYield
In methanol byproducts: NaCl; under Ar, addn. of 4 equivalents NaOMe-soln. to Ru-compd. and 2 equivalents of ligand in methanol, stirred for 1.5 h min at room temp.; evapd. in vac., residue taken up in CH2Cl2, centrifuge (NaCl), dropwise addn. to pentane, diffusion of ether into a methanolic soln.; elem. anal.;86%
2987-16-8

3,3-dimethylbutyrylaldehyde

22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol; water at 20℃; for 6h;85%
With hydrogen; palladium on activated charcoal under 1551.44 Torr; for 12h; Condensation; reduction; room t.;56%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 1551.44 Torr; for 12h; Hydrogenation; reductive alkylation;56%
76678-64-3

3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde

22839-47-0

L-Asp-L-Phe-OMe

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid at 10 - 20℃; for 2h;85%
22839-47-0

L-Asp-L-Phe-OMe

63-91-2

L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide for 6h; Heating;83%
22839-47-0

L-Asp-L-Phe-OMe

307501-98-0

(1,1,1-trifluoroethyl) phenyl iodonium (N,N'-bis-trifluoromethylsulfonyl) imide

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
80%
22839-47-0

L-Asp-L-Phe-OMe

136983-81-8

sodium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine

Conditions
ConditionsYield
With sodium hydroxide In water78%
76678-64-3

3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde

22839-47-0

L-Asp-L-Phe-OMe

N-[N-[3-(3-benzyloxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid at 10℃;78%
24424-99-5

di-tert-butyl dicarbonate

22839-47-0

L-Asp-L-Phe-OMe

40944-73-8

methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 18h;72%
22839-47-0

L-Asp-L-Phe-OMe

2-azido-α-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate; sodium hydroxide In methanol; dichloromethane; water at 20℃; for 18h; pH=9 - 9.5;70%
22839-47-0

L-Asp-L-Phe-OMe

(3-hydroxy-4-methoxy)cinnamaldehyde

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
Stage #1: L-Asp-L-Phe-OMe; 3-hydroxy-4-methoxycinnamalaldehyde With sodium tetrahydroborate; acetic acid at 10 - 20℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In ethanol; water under 2585.81 Torr; for 10h;
66%
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Chemistry

Molecular Structure:

Molecular Formula: C14H18N2O5
Molecular Weight: 294.3031
IUPAC Name: (3S)-3-Amino-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
Synonyms of Aspartame (CAS NO.22839-47-0): L-Phenylalanine, L-alpha-aspartyl-, 2-methyl ester ; L-Phenylalanine, N-L-alpha-aspartyl-, 1-methyl ester ; Succinamic acid, 3-amino-N-(alpha-carboxyphenethyl)-, N-methyl ester, stereoisomer
CAS NO: 22839-47-0
Classification Code: Flavoring Agents ; Food Additives ; Human Data ; Reproductive Effect ; Sweetener ; Sweetening Agents
Melting point: 242-248 °C 
Index of Refraction: 1.557
Molar Refractivity: 74.01 cm3
Molar Volume: 229.7 cm3
Surface Tension: 55 dyne/cm
Density: 1.28 g/cm3
Flash Point: 277.8 °C
Enthalpy of Vaporization: 85.5 kJ/mol
Boiling Point: 535.8 °C at 760 mmHg
Vapour Pressure: 2.6E-12 mmHg at 25°C

Uses

 Aspartame (CAS NO.22839-47-0) is an artificial sweetener. It is one of the main sugar substitutes used by people with diabetes.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Toksikologicheskii Vestnik. Vol. (3), Pg. 37, 1996.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (3), Pg. 37, 1996.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Toksikologicheskii Vestnik. Vol. (3), Pg. 37, 1996.
rat LD50 oral > 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (3), Pg. 37, 1996.
women TDLo oral 3710ug/kg (3.71mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 104, Pg. 207, 1986.

Safety Profile

Human systemic effects by ingestion: allergic dermatitis. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Safety Statements of Aspartame (CAS NO.22839-47-0): 22-24/25 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2

Analytical Methods

For occupational chemical analysis use NIOSH: Aspartame 5031.

Specification

The artificial sweetener Aspartame (CAS NO.22839-47-0) has been the subject of controversy since its initial approval by the U.S. Food and Drug Administration (FDA) in 1974. Concerns have been raised about the quality of the research supporting its safety and the long-term effects that increased consumption could have on the public.