(-)-Asparagine

-3.82

log Kow = -3.82

-3.82

-0.74

1.543 g/cu cm at 15/4 °C

Orthorhombic bisphenoidal crystals

29400

Practically insoluble in methanol, ethanol, ether, benzene. Soluble in acids and alkalies

In water, 2.94X10+4 mg/L at 25 °C

29.4 mg/mL

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

234-235 °C

234-235 °C

234 - 235 °C

0.00000005 [mmHg]

Specific optical rotation: -5.3 at 20 °C (c= 1.3 mg/L); +34.26 at 20 °C (c= 2.24 mg/L in 3.4N Hcl); -635 at 20 °C (c= 11.23 mg/L in 2.5N NaOH) /L-asparagine/

Specific optical rotation: +5.41 at 20 °C (c= 1.3 mg/L) /D-asparagine/

Dry Powder

Solid; [Merck Index] White hygroscopic powder; [Alfa Aesar MSDS]

Solid

Positive

2.12

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

8.82 (at 18 °C)

pKa1 = 2.02; pKa2 = 8.80

This chemical does not meet GHS hazard criteria for 100% (164 of 164) of all reports.

Not Classified；Reported as not meeting GHS hazard criteria by 164 of 164 companies. For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 164 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 164 of 164 reports by companies.；There are 0 notifications provided by 0 of 164 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical: L-Asparagine

L-Asparagine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of L-Asparagine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21618

Asparagine: Does not have an individual approval but may be used under an appropriate group standard

L-Asparagine: Does not have an individual approval but may be used under an appropriate group standard

IMAP assessments - L-Asparagine: Environment tier I assessment；Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health

Causes weight loss, effects on phosphatases, lipids (including transport), and transaminases, changes in brain, kidney, and testicular weights, hyperglycemia, and changes in potassium in 90-day constant oral studies of rats; [RTECS] May cause irritation; [Alfa Aesar MSDS]

L-Asparagine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

Not Classified

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that asparagine is expected to have very high mobility in soil(SRC). Asparagine will not volatilize from moist soil surfaces since it exists as either an anion, cation, or zwitterion(3) in the environment depending upon pH, and ionic compounds do not volatilize. Asparagine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-8 mm Hg(SRC), determined from a fragment constant method(4). Amino acids are an important nitrogen source for microorganisms, and are readily assimilated by microbes(5). A screening study using activated sludge, indicated that asparagine reached approximately 25% of its theoretical BOD over a 1 day incubation period(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that asparagine is not expected to adsorb to suspended solids and sediment(SRC). Asparagine is an amino acid with pKa1 = 2.02, pKa2 = 8.80, and isoelectric point of 5.41(3). This indicates that asparagine will exist as a cation, anion, or zwitterion depending upon pH, and ionic compounds do not volatilize from water(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -3.82(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Amino acids are an important nitrogen source for microorganisms, and are readily assimilated by microbes(7). A screening study using activated sludge, indicated that asparagine reached approximately 25% of its theoretical BOD over a 1 day incubation period(8). Asparagine contains an amide functional group which may be susceptible to hydrolysis(9); however, the rate of this reaction is not known(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), asparagine, which has an estimated vapor pressure of 4.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase asparagine may be removed from the air by wet and dry deposition(SRC). Amino acids have weak absorption bands with tails extending beyond 290 nm(3), indicating the potential for direct photolysis(SRC). The rate of this potential reaction for asparagine is not known(SRC).

Asparagine was reported in the following foods (mg/g): cheese 40 to 300; asparagus 5.4 to 108; cocoa (raw) 30.9, roasted at 125 °C 14.5, roasted at 135 °C 9.4; potato 0.5-10; rye 0.2 to 2.8; wheat 0.02 to 2; corn 0.6 to 1(1).

Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for asparagine can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that asparagine is expected to have very high mobility in soil(SRC).

Asparagine is a non essential amino acid that is widely distributed in animals and plants, both free and combined with proteins(1).

/OTHER TOXICITY INFORMATION/ ...Because exposure of humans to acrylamide can come from both external sources and the diet, a need exists to develop a better understanding of its formation and distribution in food and its role in human health. To contribute to this effort, this integrated review presents data on the chemistry, analysis, metabolism, pharmacology, and toxicology of acrylamide. Specifically covered are the following aspects: nonfood and food sources; exposure from the environment and the diet; mechanism of formation in food from asparagine and glucose; asparagine-asparaginase relationships; Maillard browning-acrylamide relationships; quenching of protein fluorescence; biological alkylation of amino acids, peptides, proteins, and DNA by acrylamide and its epoxide metabolite glycidamide; risk assessment; neurotoxicity, reproductive toxicity, and carcinogenicity; protection against adverse effects; and possible approaches to reducing levels in food. ... Neurotoxicity appears to be the only documented effect of acrylamide in human epidemiological studies; reproductive toxicity, genotoxicity/clastogenicity, and carcinogenicity are potential human health risks on the basis of only animal studies. A better understanding of the chemistry and biology of pure acrylamide in general and its impact in a food matrix in particular can lead to the development of improved food processes to decrease the acrylamide content of the diet.

/OTHER TOXICITY INFORMATION/ The discovery of the formation of acrylamide in fried and baked foods containing high levels of starch and the amino acid asparagine, prompted widespread concern. Both processed and home cooked foods are affected and this has led to the increased study of variations in cooking and processing conditions to minimize formation. While changes in cooking protocols have been in part successful, particularly when lower frying and baking temperatures are used, pretreatments to reduce levels of acrylamide by prevention of formation or acceleration of destruction have been investigated. In this study, a range of pretreatments of grilled potato were investigated and compared with surface washing to remove asparagine and reducing sugars. Synergies were observed between different treatments, and reductions of up to 40% were achieved in a non-optimized system.

/OTHER TOXICITY INFORMATION/ The relationship between acrylamide and its precursors, namely free asparagine and reducing sugars, was studied in simple cakes made from potato flake, wholemeal wheat and wholemeal rye, cooked at 180 degrees C, from 5 to 60 min. Between 5 and 20 min, large losses of asparagine, water and total reducing sugars were accompanied by large increases in acrylamide, which maximized in all three products between 25 and 30 min, followed by a slow linear reduction. Acrylamide formation did not occur to any extent until the moisture contents of the cakes fell below 5%. A comparison of each type of cake with a commercial product, made from the same food material, showed that acrylamide levels in all three commercial products were well below the maximum levels in the cooked cakes.

Aspargine's production and use in biochemical research, preparation of culture media, and medicine(1) may result in its release to the environment through various waste streams(SRC).

AEROBIC: Amino acids are an important nitrogen source for microbes and degrade readily in the environment(1). Asparagine at a concentration of 500 mg/L, achieved 10.3, 19.5 and 24.7% of its theoretical BOD using 2500 mg/L activated sludge in a Warburg respirometer study over a 6, 12 and 24 hour incubation periods, respectively(2).

No indication of carcinogenicity to humans (not listed by IARC).

An estimated BCF of 3 was calculated for asparagine(SRC), using a log Kow of -3.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Asparagine is an amino acid with pKa1 = 2.02, pKa2 = 8.80, and isoelectric point of 5.41(1). This indicates that asparagine will exist primarily as a cation in strongly acidic environments, an anion under highly alkaline conditions, and as the zwitterion from weakly acidic to weakly alkaline pH(SRC). Volatilization from water and moist soil surfaces will not occur since ionic species do not volatilize(SRC). Volatilization from dry soil surfaces is not expected(SRC), based upon an estimated vapor pressure of 4.8X10-8 mm Hg at 25 °C determined from a fragment constant method(2).

Asparagine is an amino acid with pKa1 = 2.02, pKa2 = 8.80, and an isoelectric point of 5.41(1). This indicates that asparagine will exist primarily as a cation in strongly acidic environments, an anion under highly alkaline conditions, and as the zwitterion from weakly acidic to weakly alkaline pH(SRC). Asparagine contains an amide functional group which may be susceptible to hydrolysis(2); however, the rate of this reaction is not known(SRC). Amino acids have weak absorption bands with tails extending beyond 290 nm(3), indicating the potential for direct photolysis(SRC). The sunlight photolysis of 0.1 M aspartic acid at pH 7 to malonic acid has been demonstrated(4). The rate of this potential reaction for asparagine is not known(SRC).

Chemical: L-Asparagine

L-Asparagine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of L-Asparagine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21618

Asparagine: Does not have an individual approval but may be used under an appropriate group standard

L-Asparagine: Does not have an individual approval but may be used under an appropriate group standard

L-Asparagine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

A possible requirement for dietary asparagine during lactation was investigated by measuring any adverse effect of maternal asparagine deprivation on the body growth and brain development of nursing rat pups. Each dam was given 7 pups to nurse. Three groups of 5 dams each were deprived from the 1st (T1), 8th (T2), or 15th (T3) day of lactation until weaning (day 22); at weaning, the pups of each group weighed approximately 10% less than those of asparagine-fed controls. Brain development was also affected: the cerebra of T3 pups contained less cholesterol and cerebrosides than control pups, indicating decreased myelination. Both T2 and T3 pups required more trials in a water maze to acquire a learned behavior than control pups. T1, T2, and T3 pups also displayed higher seizure thresholds. The groups of pups whose brains contained the lowest amounts of myelin lipids (T3) were those who displayed the greatest deviation in behavior from the control pups. Thus, the development of neonatal rat brain is sensitive to even mild or transient forms of malnutrition, and a requirement for dietary asparagine during lactation seems evident.

A non-essential amino acid. Asparagine is critical for the production of the body's proteins, enzymes and muscle tissue. Supplements of this amino acid are claimed to balance nervous system function.

Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.

Iron absorption in rats was evaluated with concurrent administration of each of 10 amino acid solutions and ascorbic acid. Asparagine, glycine, serine and ascorbic acid caused a statistically significant increase in iron absorption, with greatest effects for asparagine and glycine. No correlations were found between absorption increases and stability constants of the amino acid-iron complex.

All Tissues；Placenta；Prostate

Cytoplasm；Extracellular；Mitochondria

Amikacin Action Pathway；Arbekacin Action Pathway；Aspartate Metabolism；Azithromycin Action Pathway；Canavan Disease；Chloramphenicol Action Pathway；Clarithromycin Action Pathway；Clindamycin Action Pathway；Clomocycline Action Pathway；Demeclocycline Action Pathway；Total 35 pathways, visit the HMDB page for details

CIR ingredient: Asparagine

Amino acid not essential for humans; [Merck Index] Used in biochemical research, to make culture media, in the synthesis of acrylamide, and in medicine; [HSDB] Used as a flavor enhancer, flavoring agent or adjuvant, and nutritional supplement; [FDA]

Biochemical research, preparation of culture media, medicine

Synthesis of acrylamide

Use (kg; approx.) in Germany (2009): >250；Consumption (g per capita; approx.) in Germany (2009): 0.00305；Calculated removal (%): 92.1

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

2022: 38,189 lb；2021: 53,349 lb；2020: 47,749 lb

Produced by direct fermentation of carbohydrates

Isolated as a byproduct from the production of potato starch. A simple synthesis of L-asparagine from L-aspartic acid which is esterified to the beta methylester followed by treatment with ammonia.

Cosmetics -> Antistatic

L-Asparagine: ACTIVE

Asparagine: ACTIVE

Non-essential amino acid existing in the D(+) and L(-) isomeric forms as well as the racemic DL mixture. The L(-) asparagine is the most common form.

First isolated from asparagus juice

Studies on model systems of amino acids and sugars have indicated that acrylamide can be generated from asparagine or from amino acids that can produce acrylic acid either directly such as beta-alanine, aspartic acid and carnosine or indirectly such as cysteine and serine. The main pathway specifically involves asparagine and produces acrylamide directly after a sugar-assisted decarboxylation and 1,2-elimination steps and the second non-specific pathway involves the initial formation of acrylic acid from different sources and its subsequent interaction with ammonia to produce acrylamide.

Structural considerations dictate that asparagine alone may be converted thermally into acrylamide through decarboxylation and deamination reactions. However, the main product of the thermal decomposition of asparagine was maleimide, mainly due to the fast intramolecular cyclization reaction that prevents the formation of acrylamide. On the other hand, asparagine, in the presence of reducing sugars, was able to generate acrylamide in addition to maleimide. ...