L-Asparaginic acid
L(+)-Aspartic acid
CAS: 56-84-8
Molecular Formula: C4H7NO4
L-Asparaginic acid - Names and Identifiers
| Name | L(+)-Aspartic acid |
| Synonyms | H-Asp-OH asparagicacid Asparagic acid L-Aspantic acid asparaginsaeure L-Aspartic acid asparaginicacid Asparaginic acid L-Asparaginic acid L(+)-Aspartic acid (s)-butanedioicaci L-(+)-Aspartic acid L-Aminosuccinic acid alpha-Aminosuccinic acid L-2-Aminobutanedioic acid |
| CAS | 56-84-8 |
| EINECS | 200-291-6 |
| InChI | InChI=1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 |
| InChIKey | CKLJMWTZIZZHCS-REOHCLBHSA-N |
L-Asparaginic acid - Physico-chemical Properties
| Molecular Formula | C4H7NO4 |
| Molar Mass | 133.1 |
| Density | 1.66 |
| Melting Point | >300°C (dec.)(lit.) |
| Boling Point | 245.59°C (rough estimate) |
| Specific Rotation(α) | 25 º (c=8, 6N HCl) |
| JECFA Number | 1429 |
| Water Solubility | 5 g/L (25 ºC) |
| Solubility | Soluble in boiling water, slightly soluble in water (0.5%) at 25°C, easily soluble in dilute acid and sodium hydroxide solution, insoluble in ethanol and ether |
| Appearance | White crystal or crystalline powder |
| Color | White |
| Odor | acid taste |
| Maximum wavelength(λmax) | ['λ: 260 nm Amax: 0.20', , 'λ: 280 nm Amax: 0.10'] |
| Merck | 14,840 |
| BRN | 1723530 |
| pKa | 1.99(at 25℃) |
| PH | 2.5-3.5 (4g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidising agents. |
| Refractive Index | 1.4540 (estimate) |
| MDL | MFCD00002616 |
| Physical and Chemical Properties | Melting point 230°C specific optical rotation 25 ° (c = 8, 6N HCl) water-soluble 5g/L (25°C) |
| Use | Used for synthetic sweeteners, medicine for the treatment of heart disease, used as liver function promoter, ammonia antidote, fatigue remover and amino acid infusion components |
L-Asparaginic acid - Risk and Safety
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | CI9098500 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29224995 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 intraperitoneal in mouse: 6gm/kg |
L-Asparaginic acid - Upstream Downstream Industry
| Raw Materials | Ammonium hydroxide Fumaric acid Charcoal Sulfuric acid Ammonia |
| Downstream Products | L-Alanine DL-Aspartic Acid calcium dihydrogen di-L-aspartate |
L-Asparaginic acid - Nature
Open Data Verified Data
white crystals or crystalline powder with a sour taste. Insoluble in ethanol and ether. The combustion produces toxic ammonia oxide fumes.
Last Update：2024-01-02 23:10:35
L-Asparaginic acid - Preparation Method
Open Data Verified Data
It is obtained from fumaric acid and ammonia by the action of aspartase of Pseudomonas trefoil or Brevibacterium ammonia-producing.
Last Update：2022-01-01 09:27:37
L-Asparaginic acid - Use
Open Data Verified Data
can be used as biochemical reagents, culture medium and organic synthesis intermediates. It is used in medicine as a component of heart disease drugs, liver function promoters, ammonia antidote, fatigue eliminator and amino acid infusion. It is also used as a preservative in the food industry.
Last Update：2022-01-01 09:27:37
L-Asparaginic acid - Properties and stability
1. The properties are stable at normal temperature and pressure.
2. For natural products, non-toxic.
3. Exist in tobacco, smoke
Last Update：2024-04-10 22:29:15
L-Asparaginic acid - Synthetic Methods
1. L-aspartic acid synthesis and fermentation method. The synthesis method is mainly based on maleic acid or fumaric acid or their esters as raw materials, under pressure with ammonia treatment, and then hydrolysis. Racemic aspartic acid can be easily synthesized, but there is no ideal method for resolving racemates. The product can be obtained in high yield by adding fumaric acid and ammonia under the action of enzyme. This method is the main method of industrial production because only the levorotatory body is produced and the yield is high.
2. From fumaric acid, ammonia in the clover Pseudomonas or ammonia producing short bacteria under the action of aspartate enzyme.
Maleic acid, fumaric acid or their esters as raw materials, in the role of enzymes with ammonia addition.
Last Update：2024-04-10 22:29:15
L-Asparaginic acid - Toxicity and use limits
toxicity
can be used safely in food (FDA & sect;172.320,2000).
usage limit
- accounts for 7.0% of total protein in food (including asparagine; FDA & sect;172.320,2000)
- FEMA(mg/kg): baked food, meat product, meat soup, condiment, 250; Non-alcoholic beverage 150
maximum allowable amount of food additive
The Chinese name of the additive is allowed to use the Chinese name of the food additive function maximum allowable usage (g/kg) maximum allowable residue (g/kg)
l-aspartic acid food flavors the maximum allowable amount and the maximum allowable residual amount of each flavor component used in the preparation of flavors in GB 2760 shall not exceed
Last Update：2024-04-10 22:29:15
L-Asparaginic acid - Identification and content analysis
identification test
take 1% sample solution 5ml and ninhydrin test solution (TS 250) a total of heat, should appear blue purple.
content analysis
same as "01107,DL-aspartic acid".
Last Update：2024-04-10 22:29:15
L-Asparaginic acid - Supplementary Information
| chemical properties | White Crystal or crystalline powder, slightly acidic taste. Soluble in boiling water, 25 ° C micro-soluble in water (0.5%), soluble in dilute acid and sodium hydroxide solution, insoluble in ethanol, ether, heated to 270 ° C decomposition, isoelectric point 2.77, the specific rotation is related to the dissolved solvent. In the acid solution, it is right-handed, the alkali solution is left-handed, and the aqueous solution is right-handed. [Α] 25D +5.05 (C = 0.5-2.0g/ml, H2O). |
| purpose | as the electrolyte supplement medicine in amino acid infusion, potassium, calcium and other inorganic ion supplements, fatigue recovery agent. Potassium magnesium aspartate injection or oral liquid, for cardiac glycoside poisoning caused by arrhythmia and premature beat, tachycardia, hypokalemia, hypomagnesemia, heart failure, myocardial infarction, angina, hepatitis, cirrhosis and other diseases. Is low toxicity, the goods should not be injected without dilution, renal insufficiency and atrioventricular block with caution. |
| purpose | can be used as ammonia antidote, liver function promoter, fatigue recovery agent and other pharmaceuticals, can be prepared L-sodium aspartate food additives and additives for various cool drinks, can also be used as biochemical reagents, medium and intermediates in organic synthesis. |
| purpose | used for synthetic sweeteners, used in the treatment of heart disease in medicine, used as liver function promoter, ammonia antidote, fatigue remover and amino acid infusion components, etc. |
| purpose | nutritional supplement and flavoring agent. Added to a variety of cool drinks. It is used as ammonia antidote, liver function promoter and fatigue recovery agent in medicine. |
| purpose | td is used in biochemical studies, as a fatigue recovery agent, ammonia antidote, and as a clinical diagnostic agent.|
| production method | with DL-aspartic acid as raw material, under the condition of pH>7, acylation reaction with chloroacetamide was carried out, followed by acidification, acetone extraction and activated carbon treatment, under the condition of pH = 7-7.2, the crude product was separated by renal acylase II, acidified by HCl, treated with activated carbon, and then purified and dried to obtain a finished product. |
| production method | a calcium salt of L-glutamic acid and L-aspartic acid is obtained from various L-aspartic acid-rich proteins by acid hydrolysis followed by neutralization with calcium hydroxide, and then separated. The yield was high by adding ammonia to fumaric acid with enzyme. Obtained from the fermentation of sugars by E. Coli. |
| production method | the preparation method of L-aspartic acid is a synthesis method and a fermentation method. The synthesis method is mainly based on maleic acid or fumaric acid or their esters as raw materials, under pressure with ammonia treatment, and then hydrolysis. Racemic aspartic acid can be easily synthesized, but there is no ideal method for resolving racemates. The product can be obtained in high yield by adding fumaric acid and ammonia under the action of enzyme. This method is the main method of industrial production because only the levorotatory body is produced and the yield is high. |
| production method | L-aspartic acid is mainly produced enzymatically. L-aspartic acid is produced by the action of L-aspartase on fumaric acid (trans-succinic acid) and ammonia. Culture culture of Escherichia coli as1.881. Ordinary broth medium is bevel medium, and the composition of the flask medium is: corn steep liquor 7.5%, fumaric acid 2.0%,MgSO4 · 7 H2O 0.02%. The solution is adjusted to pH 6.0 with ammonia, boiled and filtered, A 500ml Erlenmeyer flask was filled with 50-100ml of culture medium. Take the cultured seeds on the fresh slope or in the liquid, inoculate and shake the flask culture medium, shake the culture at 37 ℃ for 24h, and gradually expand the culture to the scale of 1000-2000L, the pH was adjusted to 5.0 with 1mol/L HCl, maintained at 45 ° C. For 1H, cooled to room temperature, and centrifuged in a rotary high-speed centrifuge to collect cells containing aspartase. The immobilized aspartate enzyme was made into a bioreactor. Coli wet bacteria 20kg, suspended in the culture supernatant after centrifugation 80L (or 80L physiological saline), heat preservation 40 ℃ and then add 90L heat preservation 40 ℃ 12% gelatin solution and 1.0% glutaraldehyde solution, after thoroughly stirring, it is allowed to cool and solidify, and then immersed in 0.25% glutaraldehyde solution. After overnight at 5 ℃, it is cut into small pieces of 3-5 mm3 in size, it was soaked in 0.25% glutaraldehyde solution at 5 ℃ overnight, then taken out to wash with distilled water and filtered to obtain immobilized E containing aspartase. Coli, which was loaded into a packed bioreactor for standby. The 1 mol/L ammonium fumarate (containing 1mmol/L MgCl2,pH8.5) substrate solution was converted and continuously flowed through the bioreactor at a certain space velocity (SV), the conversion solution was obtained by controlling the maximum conversion rate to be greater than 95%. Preparation and purification of crude product the conversion solution was gradually added with 1 mol/L HCl, adjusted to pH 2.8, left overnight at 5 °c for crystallization, filtered and washed with water, the product was dried by filtration and dried at 105 ° C. To obtain crude L-aspartic acid. The crude product is recrystallized with dilute ammonia water, dissolved into 15% solution (pH5.0) with ammonia water, then added with 1% activated carbon, heated at 70 ℃, stirred and decolorized for 1H, and then filtered to remove the slag while hot, the filtrate was cooled, incubated overnight at 5 °c for crystallization, and the crystals were taken by filtration and vacuum dried at 85 °c to obtain a finished L-aspartic acid product. |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | Peritoneal-rat LD50: 6000 mg/kg |
| flammability hazard characteristics | flammable; Toxic NOx smoke from combustion |
| storage and transportation characteristics | ventilation and low temperature drying |
| extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
Last Update：2024-04-10 22:29:15
L-Asparaginic acid - Reference Information
| FEMA | 3656 | L-ASPARTIC ACID |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| identification test | 1% sample solution (5ml) was co-heated with ninhydrin test solution (TS -250), blue-purple should appear. |
| content analysis | same as "01107,DL-aspartic acid". |
| toxicity | can be used safely in foods (FDA § 172.320,2000). |
| usage limit | accounts for 7.0% of the total protein in food (including asparagine; FDA § 172.320,2000). FEMA(mg/kg): baked food, meat product, meat soup, condiment, 250; Non-alcoholic beverage 150. |
| Use | for electrolyte supplement medicine in amino acid infusion, potassium, calcium and other inorganic ion supplements, fatigue recovery agent, etc. Potassium magnesium aspartate injection or oral liquid, for cardiac glycoside poisoning caused by arrhythmia and premature beat, tachycardia, hypokalemia, hypomagnesemia, heart failure, myocardial infarction, angina, hepatitis, cirrhosis and other diseases. Is low toxicity, the goods should not be injected without dilution, renal insufficiency and atrioventricular block with caution. it can be used as ammonia antidote, liver function promoter, fatigue recovery agent and other pharmaceuticals, and can be used as L-sodium aspartate food additives and additives for various cool drinks. It can also be used as biochemical reagents, medium and intermediates in organic synthesis. It is used for synthetic sweeteners, for the treatment of heart disease in medicine, as a liver function promoter, ammonia antidote, fatigue eliminator and amino acid infusion component, etc. Nutritional supplement, dimmer flavor enhancer. Added to a variety of cool drinks. It is used as ammonia antidote, liver function promoter and fatigue recovery agent in medicine. used in biochemical research, used as fatigue recovery agent, ammonia antidote, clinical diagnostic drug. The major neurotransmitter that excites fast synapses |
| production method | acylation of DL-aspartic acid with chloroacetamide at pH>7, then after acidification, acetone extraction and activated carbon treatment, under the condition of pH = 7-7.2 with renal acylase II resolution, HCl acidification, activated carbon treatment to obtain the crude product, and then purified and dried to obtain the finished product. A calcium salt of L-glutamic acid and L-aspartic acid is obtained from various L-aspartic acid-rich proteins, which are hydrolyzed with acid and then neutralized with calcium hydroxide, and then separated. The yield was high by adding ammonia to fumaric acid with enzyme. Obtained from the fermentation of sugars by E. Coli. there are synthesis and fermentation methods of L-aspartic acid. The synthesis method is mainly based on maleic acid or fumaric acid or their esters as raw materials, under pressure with ammonia treatment, and then hydrolysis. Racemic aspartic acid can be easily synthesized, but there is no ideal method for resolving racemates. The product can be obtained in high yield by adding fumaric acid and ammonia under the action of enzyme. This method is the main method of industrial production because only the levorotatory body is produced and the yield is high. L-aspartic acid is mainly produced by enzymatic method. L-aspartic acid is produced by the action of L-aspartase on fumaric acid (trans-succinic acid) and ammonia. Culture culture of Escherichia coli as1.881. Ordinary broth medium is bevel medium, and the composition of the flask medium is: corn steep liquor 7.5%, fumaric acid 2.0%,MgSO4 · 7 H2O 0.02%. The solution is adjusted to pH 6.0 with ammonia, boiled and filtered, A 500ml Erlenmeyer flask was filled with 50-100ml of culture medium. Take the cultured seeds on the fresh slope or in the liquid, inoculate and shake the flask culture medium, shake the culture at 37 ℃ for 24h, and gradually expand the culture to the scale of 1000-2000L, the pH was adjusted to 5.0 with 1mol/L HCl, maintained at 45 ° C. For 1H, cooled to room temperature, and centrifuged in a rotary high-speed centrifuge to collect cells containing aspartase. The immobilized aspartate enzyme was made into a bioreactor. Coli wet bacteria 20kg, suspended in the culture supernatant after centrifugation 80L (or 80L physiological saline), heat preservation 40 ℃ and then add 90L heat preservation 40 ℃ 12% gelatin solution and 1.0% glutaraldehyde solution, after thoroughly stirring, it is allowed to cool and solidify, and then immersed in 0.25% glutaraldehyde solution. After overnight at 5 ℃, it is cut into small pieces of 3-5 mm3 in size, it was soaked in 0.25% glutaraldehyde solution at 5 ℃ overnight, then taken out to wash with distilled water and filtered to obtain immobilized E containing aspartase. Coli, This was loaded into a packed bioreactor for standby use. The 1 mol/L ammonium fumarate (containing 1mmol/L MgCl2,pH8.5) substrate solution was converted and continuously flowed through the bioreactor at a certain space velocity (SV), the conversion solution was obtained by controlling the maximum conversion rate to be greater than 95%. Preparation and purification of crude product the conversion solution was gradually added with 1 mol/L HCl, adjusted to pH 2.8, left overnight at 5 °c for crystallization, filtered and washed with water, the product was dried by filtration and dried at 105 ° C. To obtain crude L-aspartic acid. The crude product is recrystallized with dilute ammonia water, dissolved into 15% solution (pH5.0) with ammonia water, then added with 1% activated carbon, heated at 70 ℃, stirred and decolorized for 1H, and then filtered to remove the slag while hot, the filtrate was cooled, incubated overnight at 5 °c for crystallization, and the crystals were taken by filtration and vacuum dried at 85 °c to obtain a finished L-aspartic acid product. |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | intraperitoneal-rat LD50: 6000 mg/kg |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:06
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Raw Materials for L-Asparaginic acid
Downstream Products for L-Asparaginic acid