Name | L-Cystine |
Synonyms | Cystine L-Cystine 1-cystine Dicysteine (H-Cys-OH)2 H-(Cys)_2-OH L-Cystine,food grade 3,3'-Dithiodialanine 3,3'-dithiobis-l-alanin Alanine, 3,3'-dithiobis- (H-Cys-OH)2 (Disulfide bond) L-Cystine, synthetically derived 3,3'-dithiobis(2-aminopropanoicacid) 3,3'-Dithiobis(2-aminopropanoic acid) (-)-3,3-Dithiobis(2-aminopropionic acid) L(-)-3,3-Dithiobis(2-aminopropanoic acid) (r-(r*,r*))-3,3'-dithiobis(2-aminopropanoicacid) 3,3'-dithiobis(2-amino-,(r-(r*,r*))-propanoicaci (2R,2'S)-3,3'-disulfanediylbis(2-ammoniopropanoate) 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid |
CAS | 56-89-3 24645-67-8 |
EINECS | 200-296-3 |
InChI | InChI=1/C3H6NO2S3/c5-3(6)2(4-7)1-9-8/h2H,1,4H2,(H,5,6) |
InChIKey | LEVWYRKDKASIDU-IMJSIDKUSA-N |
Molecular Formula | C6H12N2O4S2 |
Molar Mass | 240.3 |
Density | 1.68 |
Melting Point | >240 °C (dec.) (lit.) |
Boling Point | 468.2±45.0 °C(Predicted) |
Specific Rotation(α) | -224 º(c=2 in 1M HCl) |
Water Solubility | 0.112 g/L (25 ºC) |
Solubility | Very slightly soluble in water; insoluble in ethanol and other organic solvents, easily soluble in dilute acids and alkaline liquids, and easily decomposed in hot lye |
Appearance | White crystal |
Color | White |
Merck | 14,2782 |
BRN | 1728094 |
pKa | 1.0, 2.1, 8.02, 8.71(at 25℃) |
Storage Condition | 2-8°C |
Stability | Stable. Incompatible with strong oxidizing agents. |
Sensitive | Sensitive to light |
Refractive Index | -222.5 ° (C=1, 1mol/ |
MDL | MFCD00064228 |
Physical and Chemical Properties | Properties white hexagonal plate-like crystals or white crystalline powder. soluble in dilute acid and alkali solution, extremely difficult to dissolve in water, insoluble in ethanol. |
Use | Used in medicine, food, cosmetics and other industries |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
UN IDs | 2811 |
WGK Germany | 3 |
RTECS | HA2690000 |
TSCA | Yes |
HS Code | 29309014 |
Hazard Note | Irritant |
Packing Group | III |
Raw Materials | Charcoal Sodium hydroxide Hydrochloric acid |
Reference Show more | 1. Hou Lijuan, Yan Chao, Qi Xiaoru, Wang Min. Study on the aroma difference of jujube wine produced by different varieties of jujube [J]. Food industry 2017(5):208-212. 2. Yan Chao, Hou Lijuan, Qi Xiaoru, etc. Analysis on the changes of amino acids and organic acids in fermented grains during the fermentation process of jujube and Brandy [J]. Science and Technology of food industry, 2017, 38(014):121-125. 3. Wang Tingting, Changyu steel, Changpu, Zhao Yan, he Zhongmei, Zhu Hongyan, Zhang Lianxue. Changes of main components of compound mailuqi ginseng preparation and its anti-tumor effect in H22 tumor-bearing mice [J]. Journal of Jilin University (Medicine edition),2017,43(04):698-704 858-859. 4. Zhao, Zheng, et al. "Cholinium amino acids-glycerol mixtures: New class of solutions for pretreating wheat straw to facilitate enzymatic hydrolysis." Bioresource technology 245 (2017): 625-632.https://doi.org/10.1016/j.biortech.2017.08.209 5. [IF=4.952] Fengfeng Qu et al."Effect of different drying methods on the sensory quality and chemical components of black tea."Lwt Food Sci Technol. 2019 Jan;99:112 |
of hydrochloric acid with a concentration of 10 mol/L was added to the hydrolysis tank, heated to 70~80 °c, quickly put in 100 of human hair or pig hair, and then heated to °c, and 1~1. Within 5h temperature to 110~117 deg C, hydrolysis of 6.5~7H (from 100 deg C), cooling, filtration. The filtrate was added with 30% ~ 40% industrial sodium hydroxide solution under stirring. When the pH value reached 3.0, the alkali solution was decelerated and added until the pH value was 4.8, that is to get the cystine crude product (work), the mother liquor contains glutamic acid, arginine and leucine. Weigh the crude cystine (1) 150kg, add about 90kg of 10 mol/L hydrochloric acid, 360kg of water, heat to 65~70 °c, stir and dissolve 0. 5h, then add activated carbon 12kg, heating to 80~90 degrees Celsius, heat preservation 0. 5h, Plate and Frame pressure filtration. The filtrate was heated to 80-85 °c and 30% sodium hydroxide was added with stirring until the pH was stopped at 4.8. The mixture was allowed to stand, and the crystals were precipitated. The supernatant liquid was sipped, and the precipitate was separated from the bottom, and then centrifuged and dried to obtain cystine crude product (II). Weigh the crude cystine (II) lOOkg, add 1 mol/L hydrochloric acid 500L, heat to 70 ° C., and add 3-5kg of activated carbon. Then, the temperature was raised to 85 °c, and the mixture was stirred for 0.5h, followed by plate-and-frame pressure filtration. The filtrate was added with distilled water about 1.5 times the volume of the filtrate, heated to 75-80 ° C., and neutralized with 12% aqueous ammonia under stirring to pH 3.5-4.0, at which point cystine crystallized out. Centrifugal spin drying of crystallization, washing with distilled water to no chloride ion, and vacuum drying to obtain cystine finished product. The yield of human hair was 8%, and the yield of pig hair was 5%.
dangerous goods mark | Xi,Xn |
hazard category code | 36/37/38-22 |
safety instructions | 26-36-24/25 |
dangerous goods transport number | 2811 |
WGK Germany | 3 |
RTECS number | HA2690000 |
Hazard Note | Irritant |
TSCA | Yes |
PackingGroup | III |
customs code | 29309014 |
Use
1. Used for biochemical research, preparation of biological media, medically used for the prevention and treatment of hepatitis, radiation damage, various alopecia, and drug poisoning, and can also be used for acute infectious diseases, bronchial asthma, neuralgia and eczema And burns
2. Used in medicine, food, cosmetics and other industries
3. Used in medicine, cosmetics, food additives, etc.
4, nutritional supplements, flavoring agents. For the breastfeeding of milk powder. Dough strength enhancer, used in baked goods (yeast starter), baking powder.
Used medically to promote wound healing. Treatment of skin allergies, antidotes, hematopoietic agents, etc.
5. Cystine is an important component of amino acid infusion and compound amino acid preparations. It is used to prevent congenital homocystinuria, various alopecia, hepatitis, radiation damage, and giant cell reduction caused by various reasons And drug poisoning. In addition, it is also used for adjuvant treatment of acute infectious diseases, bronchial asthma, neuralgia, eczema and burns.
6. Important pharmaceutical intermediates, preparation of compound amino acid oral preparations or infusion, dyeing agents, cosmetics, dairy additives, grease antioxidants, etc. It is also used for heavy metal antidote, hepatitis and other drugs. It has the ability to promote the redox of body cells, increase white blood cells to prevent the development of pathogenic bacteria, reduce leukemia, coronary heart disease, prevent fatty liver cirrhosis, promote hair growth and prevent skin aging, but also typhoid, dysentery, influenza, etc., asthma, neuralgia, eczema and Various poisoning diseases.
7. Some tumor cell lines need cystine or cysteine in the culture medium; substances necessary for the growth of various microorganisms
8. L-cystine is a feed nutrition enhancer, which is beneficial to animal development, increases body weight and liver and kidney functions, and improves fur quality.
9. Used in biochemistry and nutrition research, medicine has the functions of promoting the oxidation and reduction of body cells, increasing white blood cells and preventing the development of pathogenic bacteria. Mainly used for various alopecia. It is also used for acute infectious diseases such as dysentery, typhoid fever, influenza, asthma, neuralgia, eczema and various poisoning diseases, and has the effect of maintaining protein configuration. It is also used as a food flavoring agent.
Production method
1. L-cystine was discovered by Wollaston from bladder stones in 1810. In 1832, Berzelius named it cystine, which is a sulfur-containing amino acid, which exists in a small amount in protein, mostly in keratin in hair, finger claws, etc. It can also be obtained by synthesis. Industrially extracted from hair, the yield can reach 7.5-8%. Only 5% of the actual production.
2. At present, both at home and abroad are produced by extraction method. Generally extracted from hair. 80kg of clean pig hair is put into 160kg of 30% hydrochloric acid, stirred and heated to 110.5 ℃ within 25min, hydrolyzed at about 115 ℃ for 9h, filtered to remove impurities with polyester cloth, neutralized the filtrate with 20%-30% sodium hydroxide solution to PH = 4.8, crystallized, and filtered to obtain crude cystine. The crude product is dissolved in 1.0-1.5mol/L hydrochloric acid, heated to 80 ℃, activated carbon with crude mass of 8%-10% is added, stirred for 30min and filtered while hot. The filtrate is neutralized to PH4.8 with industrial ammonia at 80 ℃, and filtered while hot (the filtrate can recover tyrosine) to obtain cystine. Dissolve the product in 1mol/L brine, heat to 80 ℃, and if 5% activated carbon decolorizes, add 0.1% EDTE to remove iron, stir for 30min and filter while hot. The filtrate is neutralized with ammonia at 80 ℃ until PH = 4.8, cooled, crystallized and separated, washed with water until it does not contain chloride ions and iron ions, and dried at 60-70 ℃ to obtain the finished product.
3. At present, although the fermentation and enzymatic methods for amino acid production have developed rapidly, and the production cost has decreased, the protein hydrolysis method for the production of amino acids has been greatly impacted, but the production method of acidic hydrolysis of some amino acids cannot be ignored, such as cystine, Histidine, arginine, leucine, tyrosine, serine and other amino acids are still mainly hydrolyzed. Because our country is rich in natural protein resources, such as human hair, pig hair, waste silk and so on are very good raw materials. Cystine is generally prepared with pig hair or human hair raw materials, acid hydrolysis, separation and purification (using isoelectric point precipitation method). Pig hair or human hair [HCl (hydrolysis)]& rarr;[110-117 ℃, 6.5-7h] hydrolysate [30%-40% NaOH (neutralization)]& rarr;[adjust to pH4.8, stand for 36h, filter] L-cystine crude I
Crude I[HCl, 1% activated carbon (refined)]& rarr;[85 ℃, heat preservation and decolorization for 0.5h] filtrate [12% NH4OH (neutralization)]& rarr;[adjusted to pH3.5-4]L-cystine
Hydrolysis is carried out in a hydrolysis tank (tank), 10mol/L HCl 1000kg is added, heated at 70-80 ℃, then washed and dried pig hair or human hair is about half of hydrochloric acid (500kg), and the temperature is adjusted and adjusted when it is continuously heated to 100 ℃, so that it is heated to 110-117 ℃ within 1-1.5h, heated at heat preservation and hydrolyzed for 7h (counting from 100 ℃).
The neutralization hydrolysate is introduced into the neutralization tank, 30%-40% NaOH solution is gradually added and stirred continuously, and the hydrolysate is adjusted to pH4.8 to stop alkali addition. Continue stirring for 15min, retest pH to obtain neutralization solution for 4.8, stand for 36h, filter to take precipitate, centrifuge to dry to obtain crude L-cystine I.
Rough, neutralize, take about 200kg of crude L-cystine I, add 120kg of 10mol/L HCl solution and 480kg of water (800kg in total), heat and dissolve, and keep stirring. When the temperature rises to 80 ℃, add 2% of the weight of crude solution activated carbon (about 16kg) and keep the temperature at 80-90 ℃ for decolorization for 0.5h, filter off the activated carbon, and adjust the pH value, and keep stirring, make it pH4.8, let it stand for crystallization, and then precipitate the supernatant, then spin off the bottom of the precipitation crystal to obtain L-cystine crude II.
Refining, neutralizing, taking 50kg of the above L-cystine crude II, adding 250L of HCl solution of 1mol/L, stirring and heating to dissolve it, heating to 70 ℃, adding 1% activated carbon (3kg) by weight of crude II hydrochloric acid solution, heating to 85 ℃, keeping warm and decolorizing for 0.5h, filtering off activated carbon to obtain colorless transparent filtrate. Then 1.5 times the weight of distilled water is added, heated at 75-80 ℃, stirred with 12% ammonia water to neutralize to pH3.5-4.0, the mother liquor on the crystal is sucked out while it is hot, the bottom crystal is filtered, and distilled water is used to wash off chloride ions-free, drained, and vacuum dried to obtain L-cystine.
4. After being decomposed by adding water to hair, it can be separated from other hydrolysates by using its insoluble property. Because it is prone to racemization, it can be refined by the poor solubility of hydrochloride.
5. Hair and the like are used as raw materials, neutralized and crystallized after acid hydrolysis, and then filtered and refined.
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
trait | L-cystine is a white hexagonal plate-like crystal or white crystalline powder. |
uses | L-cystine has a wide range of uses: 1. Used in biochemical research. A biological medium was prepared. For biochemical and nutritional research, medicine has to promote the body cell oxidation and reduction function, increase white blood cells and prevent the development of pathogenic bacteria and other effects. It is mainly used for various alopecia. It is also used for dysentery, typhoid fever, influenza and other acute infectious diseases, asthma, neuralgia, eczema and various poisoning diseases, and has the role of maintaining protein configuration. It is also used as a food flavoring agent. 2. Biochemical reagents for the preparation of biological media. It is also an important component of amino acid infusion and compound amino acid preparation. 3. As a feed nutrition enhancer, it is beneficial to animal development, increase body weight and liver and kidney function, and improve fur quality. 4. Can be used as cosmetic additives, can promote wound healing, prevent skin allergies and treatment of eczema and other effects. used for biochemical research, preparation of biological medium, medicine for hepatitis, prevention and treatment of radiation injury, various alopecia, and drug poisoning, can also be used for acute infectious diseases, bronchial asthma, adjunctive treatment of neuralgia and eczema and burns. used in medicine, food, cosmetics and other industries used in medicine, cosmetics, food additives, etc. nutritional supplements, flavoring agents. For breast milk powder. Dough reinforcement enhancer, used in baked food (yeast starter), baking powder. Medicinal for the promotion of wound healing. Treatment of skin allergies, antidote, hematopoietic agents. cystine is an important component of amino acid infusion and compound amino acid preparation. It is used for the prevention and treatment of congenital cysteinuria, various alopecia, hepatitis, radiation injury, giant cell reduction and drug poisoning caused by various reasons. In addition, it is also used for the adjuvant treatment of acute infectious diseases, bronchial asthma, neuralgia, eczema and burns. important pharmaceutical intermediates, preparation of compound amino acid oral preparation or infusion, dyeing agent, cosmetics, dairy additives, oil antioxidants, etc. Also used for heavy metal antidote, hepatitis and other drugs. Has the ability to promote the oxidation and reduction of the body's cells, Increase white blood cells to prevent the development of pathogenic bacteria, can reduce leukemia, coronary heart disease, prevention and treatment of fatty liver cirrhosis, promote hair growth to prevent skin aging, but also typhoid dysentery, influenza, asthma, neuralgia, eczema and various poisoning diseases. some tumor cell lines require cystine or cysteine in the culture medium; Substances necessary for the growth of various microorganisms L-cystine is a feed nutrition enhancer, which is beneficial to animal development, increase weight and liver and kidney function, improve the quality of fur. It is used in biochemical and nutritional research, and has the effects of promoting the oxidation and reduction function of body cells, increasing white blood cells and preventing the development of pathogenic bacteria in medicine. It is mainly used for various alopecia. It is also used for dysentery, typhoid fever, influenza and other acute infectious diseases, asthma, neuralgia, eczema and various poisoning diseases, and has the role of maintaining protein configuration. It is also used as a food flavoring agent. |
content analysis | the nitrogen content is measured by Kjeldahl method, and the sample size is 200mg, and the L-amino acid is equal to N × 8.58. |
toxicity | can be used safely in foods (FDA § 172.320,2000). LD50 25 g/kg rat, oral). |
Use limit | as an amino acid source, it should account for 2.3% of the total protein in food (FDA § 172.320,2000). As a dough strengthening agent, it is limited to 0.009% of the amount of flour (FDA § 184.1271,2000). |
production method | L-cystine was discovered by Wollaston in 1810 from bladder stones. In 1832, Berzelius named it cystine, which is a sulfur-containing amino acid, in a small amount of protein, contained in the hair, fingers and other keratin. It can also be obtained by synthesis. Industrial extraction from the hair, the yield of up to 7.5-8%. Only 5% in actual production. at present, extraction method is used for production at home and abroad. Generally extracted from the hair. The clean pig hair 80kg, put 160kg of 30% hydrochloric acid, 25min stirring temperature to 110.5 deg C, and hydrolysis at 115 deg C for 9H, with polyester cloth filter to remove impurities, the filtrate was neutralized with 20%-30% sodium hydroxide solution to PH = 4.8, left to stand for crystallization, and filtered to obtain crude cystine. The crude product was dissolved in 1.0-1.5mol/L hydrochloric acid, and the temperature was raised to 80 ° C., then 8-10% activated carbon was added, stirred for 30min, and filtered while hot. The filtrate was neutralized to pH 4.8 with industrial aqueous ammonia at 80 ° C. And filtered while hot (tyrosine was recovered from the filtrate) to obtain cystine. Dissolve this product in 1mol/L brine, heat to 80 ℃, and if 5% of activated carbon decolorized, then add 0.1% of ethylenediaminetetraacetic acid (EDTE) to remove iron, after stirring for 30min, it was filtered while hot. The filtrate was neutralized with ammonia water at 80 ° C. Until PH = 4.8, cooled, crystallized, separated, and washed with water until chloride ion and iron ion are not contained, The product was dried at 60-70 °c. at present, although the fermentation method and enzymatic method for amino acid production have developed rapidly, and the production cost has decreased, the protein hydrolysis method for amino acid production has been greatly impacted, but some amino acids by acidic hydrolysis of protein production methods still can not be ignored, such as cystine, histidine, arginine, leucine, tyrosine, serine and other amino acids are still mainly used hydrolysis method. Because our country has rich natural protein resources, such as human hair, pig hair, waste silk and so on are good raw materials. Cystine is usually prepared by acid hydrolysis, separation and purification (using isoelectric point precipitation method) with pig hair or human hair. Pig hair or human hair [HCl (hydrolyzed)]→[110-117 ℃, 6.5-7H] hydrolysate [30%-40% NaOH (neutralized)]→ [adjusted to pH, stand for 36H, filter] L-cystine crude I crude I[HCl, 1% activated carbon (refined)]→[85 ℃, insulation decolorizing 0.5h] filtrate [12% NH4OH (neutralized)]→ [adjusted to pH 3.5-4]L-cystine is hydrolyzed in the hydrolysis tank (tank), put 10mol/L HCl 1000kg, heated at 70-80 ℃, then put the washed and dried pig hair or human hair about half the amount of hydrochloric acid (500kg), continue to heat to 100 ℃, start to control the temperature, and raise it to 110-117 ℃ in 1-1.5H, insulation hydrolysis 7H (from 100 deg C), discharge filtration, take the filtrate (hydrolysate). The neutralized hydrolysate is introduced into the neutralized pool, and 30%-40% NaOH solution is gradually added with stirring, and the hydrolysate is adjusted to pH to stop adding alkali. The mixture was stirred for another 15min, and the pH was adjusted to 4.8 to obtain neutralization solution. The mixture was allowed to stand for 36H, The precipitate was collected by filtration, centrifuged and spin dried to obtain L-cystine crude product I. Crude, neutralized L-cystine I about 200kg, add 10mol/L HCl liquid 120kg, water 480kg (a total of 800kg), heat dissolved, and stirring, when the temperature is raised to 80 ℃, add 2% weight of activated carbon (about 16kg) of the crude solution and keep the temperature at 80-90 ℃ for 0.5h, filter to remove the activated carbon, the obtained filtrate was adjusted to pH value with 30% NaOH solution, and the mixture was stirred to pH 4.8. After crystallization, the supernatant was precipitated, the bottom precipitated crystals were spin-dried to obtain L-cystine crude product II. Refine, neutralize 50kg of L-cystine II, add 1mol/L HCl solution 250L, stir and heat to dissolve, when warming to 70 ℃, activated carbon (3kg) of 1% weight of crude II hydrochloric acid solution was added, and the temperature was raised to 85 ° C. For heat preservation and decolorization for 0.5h, and the activated carbon was filtered off to obtain a colorless transparent filtrate. Then add 1.5 times the weight of distilled water, heating 75-80 ℃, stirring with 12% ammonia neutralization to pH 3.5-4.0, while hot the crystallization of the above mother liquor suction, bottom crystallization filtration, and distilled water to wash off chloride-free, suction, vacuum drying to obtain L-cystine. after the hair is decomposed by adding water, it can be separated from other hydrolysates by using its poor solubility. Because of easy racemization, it can be refined by using the solubility difference of hydrochloride. The crystals are neutralized by acid hydrolysis using hair and the like as raw materials, and then purified by filtration. |
melting point | >240°C (dec.) (lit.) |
specific rotation | -224 °(c=2 in 1M HCl) |
boiling point | 468.2±45.0 °C(Predicted) |
density | 1.68 |
refractive index | -222.5 ° (C=1, 1mol/L HCl) |
storage conditions | 2-8°C |
solubility | 1 M HCl: 100 mg/mL |
morphology | Powder/Solid |
acidity coefficient (pKa) | 1.0, 2.1, 8.02, 8.71(at 25℃) |
color | White |
optical activity (optical activity) | [α]20/D 219±5°, c = 1% in 1 M HCl |
water solubility | 0.112 g/L (25 °C) |
Merck | 14,2782 |
BRN | 1728094 |
stability | Stable. Incompatible with strong oxidizing agents. |
InChIKey | LEVWYRKDKASIDU-IMJSIDKUSA-N |
NIST chemical information | L-Cystine(56-89-3) |