Aspartame supplier | CasNO.22839-47-0

Name
Aspartame
EINECS 245-261-3
CAS No. 22839-47-0
Article Data50
CAS DataBase
Density 1.28 g/cm³
Solubility Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
Melting Point 242-248 °C
Formula C₁₄H₁₈N₂O₅
Boiling Point 535.8 °C at 760 mmHg
Molecular Weight 294.307
Flash Point 277.8 °C
Transport Information
Appearance White powder or tablets
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

Conditions	Yield
With hydrogen; palladium on activated charcoal	97%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydroxylamine hydrochloride In methanol	83%

: 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

Conditions	Yield
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

Conditions	Yield
In water; tert-butyl alcohol	70%

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

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; acetic acid; thiourea; sodium chloride In methanol; 1,1-dichloroethane; water	A n/a B 48%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
With sulfuric acid In methanol; 1,2-dichloro-ethane	21.9%

...Expand

: 104413-44-7
L-aspartic anhydride hydrochloride

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
	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

Conditions	Yield
With potassium hydroxide; hydroxylamine hydrochloride In methanol; ethyl acetate	21%

: 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

Conditions	Yield
In methanol; 1,2-dichloro-ethane	19.2%

: 4976-94-7
Boc-Asp(OtBu)-Phe-OMe

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
With trifluoroacetic acid

: 5262-07-7
Z-Asp(OBzl)-Phe-OMe

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: aspartame hemihydrate, form I, ball-milled

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
at 130℃; Kinetics;

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 22839-47-0
L-Asp-L-Phe-OMe

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In methanol; water; ethyl acetate	A n/a B 97%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 22839-47-0
L-Asp-L-Phe-OMe

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 2987-16-8
3,3-dimethylbutyrylaldehyde

: 22839-47-0
L-Asp-L-Phe-OMe

: 165450-17-9
neotame

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
	80%

: 22839-47-0
L-Asp-L-Phe-OMe

: 136983-81-8
sodium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine

Conditions

Conditions	Yield
With sodium hydroxide In water	78%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Aspartame Chemical Properties

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

Aspartame Uses

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

Aspartame 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.

Aspartame Safety Profile

Human systemic effects by ingestion: allergic dermatitis. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.
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

Aspartame Analytical Methods

For occupational chemical analysis use NIOSH: Aspartame 5031.

Aspartame 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.

Product Name

Aspartame

Synthetic route

Aspartame Chemical Properties

Aspartame Uses

Aspartame Toxicity Data With Reference

Aspartame Safety Profile

Aspartame Analytical Methods

Aspartame Specification

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