ASPARTAME

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H18N2O5
Molecular Weight	294.3031
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O

InChI

InChIKey=IAOZJIPTCAWIRG-QWRGUYRKSA-N

InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C14H18N2O5
Molecular Weight	294.3031
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11372003 | https://www.ncbi.nlm.nih.gov/pubmed/21372000 | http://www.naturodoc.com/library/nutrition/aspartame.htm

Aspartame (l-aspartyl-l-phenylalanine methyl ester) known to the public as NutraSweet has been the subject of controversy since it first became an ingredient in food products. The perceived sweetness of aspartame in humans is due to its binding of the heterodimer G-protein coupled receptor formed by the proteins TAS1R2 and TAS1R3. Aspartame was used in experiments on animals to study its role in delays of osteoarthritis. It was shown, that aspartame improved bone cortical density and muscle mass, and might contribute to a better quality of life for these diseased animals. In addition, was investigated the effect in patients with sickle cell anemia. It was revealed, that oral administration of aspartame lead inhibition of sickle cells. That effect was explained by binding aspartame with two human Bence Jones proteins: Mcg and Sea. Thus was suggested, that aspartame could interfere with sickle hemoglobin fibril formation. Then several studies showed that aspartame had no effect on the polymerization of sickle hemoglobin.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Taste receptor type 1 member 2 7 Target ID: Q8TE23 Gene ID: 80834.0 Gene Symbol: TAS1R2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11917125	Binding Agent 1037
Taste receptor type 1 member 3 14 Target ID: Q7RTX0 Gene ID: 83756.0 Gene Symbol: TAS1R3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11917125	Binding Agent 1037

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21372000	Palliative	Preclinical	Unknown Approved Use Unknown
Sickle cell anemia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11372003	Primary	Not Provided 505	Unknown Approved Use Unknown
sweetener 2 Sources: https://www.diabetes.co.uk/sweeteners/canderel.html	Primary	Approved 8307	Canderel Approved Use Unknown

PubMed

Title	Date	PubMed
Interference of rheumatoid factor activity by aspartame, a dipeptide methyl ester.	1999 Sep-Oct	10777254
Why do some dietary migraine patients claim they get headaches from placebos?	2000 May	10792367
The biochemistry of citric acid accumulation by Aspergillus niger.	2001	11791342
Effects of dietary arabinogalactan on gastrointestinal and blood parameters in healthy human subjects.	2001 Aug	11506055
Placebo expectancy effects in the relationship between glucose and cognition.	2001 Aug	11502230
Local influence to detect influential data structures for generalized linear mixed models.	2001 Dec	11764257
Selective continuous monitoring and analysis of mixtures of acesulfame-K, cyclamate, and saccharin in artificial sweetener tablets, diet soft drinks, yogurts, and wines using filter-supported bilayer lipid membranes.	2001 Dec 15	11791564
Simultaneous determination of artificial sweeteners, preservatives, caffeine, theobromine and theophylline in food and pharmaceutical preparations by ion chromatography.	2001 Dec 7	11765085
Calculation of the intake of three intense sweeteners in young insulin-dependent diabetics.	2001 Jul	11397521
Relief of fibromyalgia symptoms following discontinuation of dietary excitotoxins.	2001 Jun	11408989
Aspartame prevents the karyomegaly induced by ochratoxin A in rat kidney.	2001 May	11409539
The effect of oral aspartame administration on the balance of magnesium in the rat.	2001 Sep	11599551
Cytotoxic effects of methanol, formaldehyde, and formate on dissociated rat thymocytes: a possibility of aspartame toxicity.	2002	11991085
Investigation into the significance of task difficulty and divided allocation of resources on the glucose memory facilitation effect.	2002 Apr	11919666
Effects of L-tyrosine and carbohydrate ingestion on endurance exercise performance.	2002 Nov	12381742
Physiological mechanisms mediating aspartame-induced satiety.	2003 Apr	12782208
Wants to clear up Internet misinformation regarding aspartame.	2003 Aug 1	12906221
Estimated intake of the artificial sweeteners acesulfame-K, aspartame, cyclamate and saccharin in a group of Swedish diabetics.	2003 Feb	12623659
Construction of hybrid peptide synthetases for the production of alpha-l-aspartyl-l-phenylalanine, a precursor for the high-intensity sweetener aspartame.	2003 Nov	14622284
Aspartame and aspartame derivatives effect human thrombin catalytic activity.	2004 Dec 20	15572260
Position of the American Dietetic Association: use of nutritive and nonnutritive sweeteners.	2004 Feb	14760578
Behavioral study in the gray mouse lemur (Microcebus murinus) using compounds considered sweet by humans.	2004 Jan	14752812

Patents

Sample Use Guides

In Vivo Use Guide

23 subjects from the Sickle Cell Clinic (University of Oklahoma Health Sciences Center, Oklahoma City, Okla) consented to participate in a randomized single-dose administration of 1.5, 3.0, or 6 mg/kg aspartame.

Route of Administration: Oral

In Vitro Use Guide

For the in vitro studies, blood from 20 subjects monitored for sickle cell anemia was collected in heparinized tubes. Specimens were divided in thirds and aspartame was added to 2 tubes to yield a 1 mg/mL or 2 mg/mL concentration. Sickled cells that were present after a drop from each aliquot was added to a fresh 2% metabisulfite solution were counted 3 times. For the in vitro studies, sickled cells decreased from 28% to < 14% when 1 mg/mL aspartame was added and decreased further with 2 mg/mL.

Substance Class	Chemical Created by `admin` on `Sun Dec 18 19:26:09 UTC 2022` Edited by `admin` on `Sun Dec 18 19:26:09 UTC 2022`
Record UNII	Z0H242BBR1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASPARTAME

Official Name

English

METHYL ASPARTYLPHENYLALANATE

Common Name

English

ASPARTAME [HSDB]

Common Name

English

APM

Code

English

L-ASPARTYL-L-PHENYLALANYL METHYL ESTER

Common Name

English

E-951

Code

English

L-PHENYLALANINE, N-L-.ALPHA.-ASPARTYL-, 1-METHYL ESTER

Common Name

English

ASPARTAME [USP-RS]

Common Name

English

ASPARTAME [EP MONOGRAPH]

Common Name

English

SLADEX

Brand Name

English

EQUAL

Brand Name

English

ASPARTAME [USAN]

Common Name

English

3-Amino-N-(?-carboxyphenethyl)succinamic acid N-methyl ester

Systematic Name

English

ASPARTAME [II]

Common Name

English

NUTRASWEET

Brand Name

English

Aspartame [WHO-DD]

Common Name

English

aspartame [INN]

Common Name

English

PAL SWEET

Brand Name

English

NSC-758953

Code

English

ASPARTAME [INCI]

Common Name

English

ASPARTAME (E951)

Common Name

English

INS NO.951

Common Name

English

ASPARTAME [FHFI]

Common Name

English

SC-18862

Code

English

ASPARTAME [FCC]

Common Name

English

INS-951

Common Name

English

ZERO-CAL

Brand Name

English

ASPARTAME [MI]

Common Name

English

ASPARTAME [VANDF]

Common Name

English

ASPARTAME [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 201.66