Molecular Formula | C42H62O16 |
Molar Mass | 822.94 |
Density | 1.1442 (rough estimate) |
Melting Point | 220°C (rough estimate) |
Boling Point | 681.01°C (rough estimate) |
Specific Rotation(α) | D17 +46.2° (c = 1.5 in alc) |
Flash Point | 589.4°C |
Solubility | Soluble in methanol, DMSO, etc., insoluble in ether, glycyrrhizic acid precipitates when it meets acid. |
Vapor Presure | 0mmHg at 25°C |
Appearance | White to beige powder |
Color | White to Light Yellow |
Merck | 14,4505 |
pKa | 2.76±0.70(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Stability | Hygroscopic |
Refractive Index | 61 ° (C=1.5, EtOH) |
MDL | MFCD00065194 |
Physical and Chemical Properties | Licorice powder is light yellow powder, sweet, slightly bitter, containing 6%~ 14% glycyrrhizic acid. Pure glycyrrhizic acid is crystalline powder, sweet taste, 200~250 times of sucrose sweet, sweet storage time. The melting point was 212-217 °c. Soluble in hot water, insoluble in ether, insoluble in propylene glycol, ethanol. Stable to heat, base and salt, the solution appears to precipitate at pH 54 at 3. Mouse oral LD50 greater than 10 g/kg. ADI extension determination (FAO/WHO,1994). |
Use | As a drug, anti-inflammatory, anti-allergic; As a sweetener, widely used in various types of food |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
RTECS | MD2025000 |
HS Code | 29389090 |
licorice contains more than 100 kinds of chemical elements, the main components are glycyrrhizic acid, liquiritin and so on. Pure glycyrrhizic acid crystalline powder, sweet taste, sweetness of sucrose 200~250 times, sweet for a long time. The melting point was 212-217 °c. Soluble in water, insoluble in ether, insoluble in propylene glycol, ethanol, heat, alkali and salt stability, pH value is less than 3, the solution will precipitate.
licorice root, stem powder and fiber were extracted with water, the resulting liquid was concentrated, impurity was removed, sulfuric acid was added to precipitate glycyrrhizic acid, and then refined.
high sweetness, low thermal energy, safe and non-toxic, foaming and hemolytic effect is very low. With the use of sucrose, saccharin better. China's provisions can be used for biscuits, canned meat and poultry, seasoning, candy, preserved fruit, preserved fruit and beverage, according to the production needs of appropriate use.
This product contains anhydrous morphine (C17H19N03) per lml should be 0.0765 ~ 0.104mg; Guaiphenesin (C10H1404) should be 4.50 ~ 5.50mg; Glycyrrhizic acid (C42H62016) should be not less than 2.omg.
This product is brown or brown-black liquid; There is aroma, long-standing occasional precipitation.
expectorant and antitussive drugs.
shade, seal, and store in a cool and dry place.
each tablet containing anhydrous morphine (C17H19N03) should be 0.36~0.44mg; Containing glycyrrhizic acid (C42H62016) shall not be less than 7.3mg.
licorice extract powder (medium powder) 112.5G
Acup powder or poppy fruit extract powder 2G
camphor 2G
Star anise oil 2G
Sodium benzoate (medium powder) 2G
Made into 1000 tablets
The licorice extract is dried and ground, and sodium benzoate and acanthopanax powder are added to form granules, and then camphor and star anise oil dissolved in a small amount of ethanol are added, mixed and compressed into tablets.
This product is gray-brown tablets, brown tablets, brown tablets or film-coated tablets, remove the coating, brown or brown; There is a special odor; Easy to absorb moisture.
In addition to the disintegration time is not checked, should comply with the relevant provisions under the item of tablets (General Principle 0101).
expectorant and antitussive drugs.
sealed and stored in a dry place.
Plant source: | Licorice |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
licorice extract | glycyrrhizic acid is derived from the root and rhizome of leguminous plant licorice and is the most important active ingredient in licorice with a content of about 10%. Glycyrrhizic acid is also known as licorice saponin and licorice glycyrrhizin. It is a glycoside composed of glycyrrhetinic acid and glucuronic acid. White to yellowish crystalline powder, no smell, has a specific sweet taste, and the sweetness is about 200 times that of sucrose. Its sweetness is different from sweeteners such as sucrose. It takes a while to get sweet after the entrance, but it lasts for a long time. A small amount of liquiritin and sucrose can be combined with less 20% sucrose without the same sweetness. Although there is no aroma, it has fragrance enhancement effect. The aqueous solution is weakly acidic, and the pH value of 2% solution is 2.5~3.5. Insoluble in water, dilute ethanol. Easily soluble in hot water, viscous jelly after cooling. Glycyrrhizic acid is a triterpene saponin. In addition, there are glycyrrhizin, isoglycyrrhizin, etc. The leguminous plant licorice (Glycyrrhiza sp.) is an important traditional Chinese medicine. It is used in 74 of the 110 prescriptions of Treatise on Febrile Diseases. Glycyrrhizic acid is extracted from licorice and has a special sweet taste. It is mainly used in food. It is also used in other industries such as medicine, cosmetics and cigarettes. Because glycyrrhizic acid is often accompanied by pseudoaldosteronism in clinical application, experts have carried out a lot of chemical synthesis and structural modification on it. Glycyrrhizic acid derivatives have a wide range of clinical applications. |
licorice | licorice is the Glycyrrhiza uralensis Fisch of legume licorice. Roots and rhizomes. Perennial herb. Roots and rhizomes stout, reddish brown skin. The stem is erect, with white short hairs and bristle-like glands. Pinnate compound leaves; leaflets 7~17, ovate or broadly ovate, 2~5cm long, 1~3cm wide, apex acute or obtuse, base round, with short hairs and glands on both sides. Racemes axillary; flowers dense; calyx campanulate, with short hairs and bristling glands outside; corolla blue-purple, 1.4~2.5cm long. The pods are striped, sickle-shaped or ring-curved, with dense bristling glands on the outside; 6~8 seeds, kidney-shaped. The flowering period is from June to July. The fruit period is from July to September. Growth environment: born in sunny and dry calcareous grasslands, sandy soil on river banks and other places. Origin: Distributed in Northeast, North China, Northwest and other regions. Licorice is also an important raw material for the food industry. It can be used to process high-end preserves, candies, beverages, alcohol, meat products, cold food, pickles, condiments and many other foods. Not only have Chinese people eaten licorice since ancient times, but they are also exported overseas. Since the 1980s, with the rise of natural health food fever, there have been more and more health food developed with licorice as raw material at home and abroad. For example, more than 30 kinds of products, such as licorice tea, health vinegar, licorice beverage, licorice sweetener and so on, which are processed with licorice as raw and auxiliary materials, have also come out. the root and stem of licorice contain triterpene saponin glycyrrhizic acid, namely glycyrrhizin (Glycyrrhizin), which is the diglucuronide of glycyrrhetinic acid and is the sweet ingredient of licorice with a content of 3.63 ~ 13.06%. Analysis of 18 kinds of domestic licorice samples showed that: water soluble matter 18.7 ~ 40.54%, glycyrrhizic acid 3.63 ~ 13.06%, reducing sugar 3.38 ~ 13.06%, starch and colloid 2.04 ~ 6.32%, moisture 6.04 ~ 8.44%, ash 3.35 ~ 6.68%, etc. fig. 1 is a picture of licorice plants |
antiviral effect | glycyrrhizic acid has been clinically used to treat chronic hepatitis. Glycyrrhizic acid can significantly inhibit HIV replication in blood monocytes of HIV-positive patients in vitro. Glycyrrhizic acid also reduced morbidity and mortality in mice infected with lethal doses of influenza virus. Cinatl et al. compared the inhibition of triazole nucleoside, bacterial phenolic acid, pyrazofuranin and glycyrrhizic acid on the FFM-1 and FFM-2 of the two SARS coronaviruses, and found that glycyrrhizic acid has the strongest inhibition on virus replication. |
main application fields of glycyrrhizic acid | the application proportion of glycyrrhizic acid in various industries is as follows: 26% for medicine and cosmetics, 70% for food, and 4% for cigarettes and others. In terms of food: 1. soy sauce: glycyrrhizic acid can not only improve the salty taste to enhance the inherent taste of soy sauce, but also eliminate the bitter taste of saccharin, which has a synergistic effect on chemical flavoring agents. 2. Pickles: The halogen method of pickling pickles with saccharin can eliminate the bitter taste of saccharin. In the pickling process, it can overcome the shortcomings of fermentation failure, discoloration, and hardening caused by less sugar. 3. Seasoning: This product can be added with pickled seasoning liquid, seasoning powder or temporary seasoning during diet, which can increase sweetness and reduce the strange taste of other chemical flavoring agents. 4. bean paste: pickled small sauce herring with this product can increase sweetness and make the taste uniform. In medicine and cosmetics: 1. glycyrrhizic acid is a natural surfactant, and its aqueous solution has weak foaming property. 2. It has AGTH-like biological activity, strong antibacterial and anti-inflammatory functions, and is often used to treat mucosal diseases. It can prevent dental caries and mouth ulcers in oral hygiene products. 3. It has a wide range of compatibility, and can be used in skin care products to enhance the efficacy of other active substances in sunscreen, whitening, antipruritic, conditioning, scar healing, etc. 4. It is compounded with aescin and aescin and used as a high-efficiency antiperspirant. |
process flow of licorice extraction of glycyrrhizic acid | 1. crushing: liquorice root and stem are crushed in a pulverizer and screened for later use. 2. extraction: take 200kg of the above licorice coarse powder, put it into a 2000L enamel reactor, add 1200kg of water, slowly heat to 85~100 ℃, stir and extract for 2 hours, filter, add 1000kg of water to the filter residue, extract twice and merge the filtrate for 3 times according to the above method. 3. Concentration: pump the extract into the enamel evaporator for concentration. When concentrated to 1/5 of the original volume, filter while hot. 4. separation: the filtrate is cooled to room temperature and 95% ethanol is added to make the ethanol content in the extract reach 65%. let it stand for 24 hours, then filter to remove plant protein and polysaccharide. 5. Precipitation: take licorice filtrate, put it into a sedimentation tank, add concentrated sulfuric acid to adjust pH = 3, glycyrrhizic acid will precipitate out, filter, wash twice with deionized water, and then vacuum drain. 6. refining: add 3 times the amount of acetone to glycyrrhizic acid precipitation, heat reflux extraction for 3 hours, filter, residue reflux again and again take 2 times, merge 3 times reflux extract, filter, recover acetone, and obtain glycyrrhizic acid wet product. 7. drying: put the dry oxalic acid wet product into the drying room to dry, start to control the temperature at 45 ℃, dry for 1h, slowly raise the temperature to 85~95 ℃, close to drying, raise the temperature to 100 ℃, and finally bake at 105 ℃ for 5min. 8. crushing: the dried glycyrrhizic acid is crushed in a pulverizer and passed through a 60-80 mesh sieve to obtain glycyrrhizic acid powder. fig. 2 is the process flow chart of glycyrrhizic acid extraction from licorice |
qualitative and quantitative identification of glycyrrhizic acid | 1. qualitative identification: ① take 1~2mg of sample, place it on white porcelain plate, add 4 drops of 4% sulfuric acid solution, and gradually change to orange yellow to orange red. ② take 1g of sample, add 10ml of water, stir and dissolve, and divide it into 2 equal parts. take one part and place it in a test tube, shake strongly to generate persistent foam, add dilute H2SO4 to generate a large amount of precipitation, and add excess ammonia solution to precipitate and dissolve again. 2. quantitative identification: take 6g of sample, accurate to 1/10000, add 50ml of distilled water to dissolve, move it into a 100ml volumetric flask, dilute it to scale with ethanol, stir well, stand for 12h, take 25ml of supernatant with a pipette, place it in a beaker, add 3 drops of ammonia test solution, place it in a water bath to evaporate to a thick paste, add 30ml of water to dissolve, slowly add 5ml of 3% hydrochloric acid, let stand in ice water for about 30min, filter, wash the sediment with ice water for 4 times, use 5ml of ice water each time, discard the washing liquid and filtrate, collect the sediment and place it on filter paper for 2~3h, dry and weigh. |
Glycyrrhizic acid derivative | Glycyrrhizin ethyl ester is introduced into the sugar ligand of glycyrrhizic acid, and its thromboplastin and hemolysin are increased by nearly 3 times and 2 times respectively, while the 30-position carboxyl group is kept exposed. After the introduction of valine tert-butyl group on the glycoside, the level of hemolysin is increased by 50% compared with the 30-position carboxyl group protection, after the introduction of amino acids and short peptides on the sugar ligand of glycyrrhizic acid, its anti-SARS virus effect is about 10 times higher than that of glycyrrhizic acid, especially the introduction of glycine and lysine short peptides on the glycosidic bond, its anti-SARS The virus effect is 70 times higher than glycyrrhizic acid. fig. 3 is the structure diagram of amino acid derivatives of glycyrrhizic acid |
toxicity | natural product, non-toxic. It has detoxification and liver protection effect, LD50 805mg/kg (mouse, abdominal cavity). |
use | licorice is a traditional seasoning and traditional Chinese medicine in China with high safety. It has a special flavor and has a better effect when used in combination with sucrose and saccharin. China's regulations can be used for biscuits, canned meat and poultry, seasonings, candy, candied fruit, cold fruit and beverages, according to the production needs of appropriate use. this product has a special sweet taste. its sweetness is about 250 times that of granulated sugar. the sodium glycyrrhiza salt extracted from licorice has a sweet taste even if it is diluted 4000 times in aqueous solution. However, it is directly used as a sweetener for food and is not suitable for some foods. Generally, it can be combined with natural sugars such as granulated sugar, glucose, and syrup or with saccharin, glycine, propylene glycol, etc. to obtain more delicious sweetness. Japan produced 240 tons of glycyrrhizic acid in 1978. The raw material licorice was imported from China and Russia. The highest year was 12000 tons of imported licorice. Of the total sales in 1978, 26% was used for medicine and cosmetics, 70% was used for food, and 4% was used for cigarettes and others. The main uses in food are: 1. Soy sauce can not only improve the salty taste to enhance the inherent taste of soy sauce, but also eliminate the bitter taste of saccharin, it has a synergistic effect on chemical flavoring agents. 2. The brine method of pickling pickles with saccharin can eliminate the bitter taste of saccharin. In the pickling process, it can overcome the shortcomings of fermentation failure, discoloration, and hardening caused by less sugar. 3. Seasoning This product can be added with pickled seasoning liquid, seasoning powder or temporary seasoning during diet, which can increase the sweetness and obtain the salty taste hostile to Ba, and the strange taste of other chemical flavoring agents is low in season. 4. Bean paste pickled small sauce herring with this product can increase sweetness and make the taste uniform. In the process of licorice extraction, ammonium glycyrrhizinate is dissolved in an aqueous solution containing a calculated amount of sodium carbonate, and is concentrated under reduced pressure to obtain disodium glycyrrhizinate (C42H60Na3O16) and trisodium glycyrrhizinate (C42H59Na3O16). Also used as a food additive, as a sweetener for soy sauce and soy sauce. The LD50 injected intraperitoneally with disodium salt to mice is 1.44 g/kg, and the LD50 injected subcutaneously with trisodium salt to mice is 1.54 g/kg. As a drug, it has anti-inflammatory and anti-allergic reactions; as a sweetener, it is widely used in various foods Glycyrrhizic acid, also known as licorice saponin, is extracted from the natural plant licorice and is the main active ingredient of licorice. Glycyrrhizic acid has the effects of anti-inflammatory, anti-virus, liver-protecting and detoxifying, and enhancing immune function. Glycyrrhizic acid has adrenal cortex hormone-like effect, which can inhibit capillary permeability and relieve the symptoms of anaphylactic shock. Can reduce the serum cholesterol in patients with hypertension. Because glycyrrhizic acid has glucocorticoid-like pharmacological effects without serious adverse reactions, it is widely used in clinical treatment of various acute and chronic hepatitis, bronchitis and AIDS. It also has the functions of anti-cancer, anti-cancer, interferon inducer and cellular immunomodulator. a kind of natural plant licorice extracted, is the main active ingredient of licorice. |
production method | can be synthesized by chemistry, but currently it is extracted from licorice (see glycyrrhetinic acid, front article) the rhizome of licorice is dried and crushed to 0.833mm powder (fiber part is retained), 200kg of powder and fiber is taken, 1200kg of water is added, and the rhizome is extracted at 85~100 ℃ for 2 hours. After filtration, the filter residue is extracted with 1000kg of water for 2 hours, and the filter residue is extracted again after filtration. Merge the filtrate 3 times and concentrate to a volume of]/5 in an enamel evaporator. After cooling, 95% ethanol is added to make the ethanol concentration reach 65%, stand for 24 hours, and filter to remove impurities such as plant protein and polysaccharide. Sulfuric acid is added to the filtrate, the pH value is adjusted to 3, and glycyrrhizic acid is precipitated. After filtration and washing, add 3 times of acetone, heat and reflux for 3 hours, pour out the acetone extract, and the residue is repeatedly refluxed and extracted twice. Combine the extracts for 3 times, filter and recover acetone to obtain wet glycyrrhizic acid, dry at 45 ℃ for 1h, slowly raise the temperature to 85~95 ~ C, quickly dry, rise to 100~105 ℃, bake for 5min, and crush to obtain the finished product. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |