CI 75125
lycopene from tomato
CAS: 502-65-8
Molecular Formula: C40H56
CI 75125 - Names and Identifiers
| Name | lycopene from tomato |
| Synonyms | E 160d LYCOPENE CI 75125 LYCOSOURCE C.I. 75125 Y,Y-CAROTENE 4,4-CAROTENE JARCOPENE(TM) PSI,PSI-CAROTENE Lycopene Beadlet lycopene from tomato (5cis,5'cis,9cis,13cis)-psi,psi-carotene 2,6,10,14,19,23,27,31-OCTAMETHYL-DOTRIACONTA-2,6,8,10,12,14,16,18,20,22,24,26,30-TRIDECAENE |
| CAS | 502-65-8 |
| EINECS | 207-949-1 |
| InChI | InChI=1/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21-,36-22+,37-27-,38-28-,39-29-,40-30+ |
| InChIKey | OAIJSZIZWZSQBC-BOJOQWLHSA-N |
CI 75125 - Physico-chemical Properties
| Molecular Formula | C40H56 |
| Molar Mass | 536.87 |
| Density | 0.9380 (estimate) |
| Melting Point | 172-173°C |
| Boling Point | 644.94°C (rough estimate) |
| Flash Point | 350.7°C |
| Solubility | It is a fat-soluble pigment, soluble in other lipids and non-polar solvents, insoluble in water, insoluble in strong polar solvents such as methanol, ethanol, etc., soluble in aliphatic hydrocarbons, aromatic hydrocarbons and chlorinated hydrocarbons such as ethane, Organic solvents such as benzene and chloroform. |
| Vapor Presure | 1.33E-16mmHg at 25°C |
| Appearance | Red long needle or prism (petroleum ether) |
| Color | Red to Very Dark Red |
| Storage Condition | -70°C |
| Stability | Heat sensitive - store at -70 C. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5630 (estimate) |
| MDL | MFCD00017350 |
| Physical and Chemical Properties | One of the carotenoids. Needle-like deep red crystals (precipitated from a mixture of carbon disulfide and ethanol). Melting Point 174 °c. Flammable. Soluble in carbon disulfide (1G/50 m1), boiling ether (1g/3L), n-hexane (1g/14 L,0 C). Soluble in chloroform and benzene. Slightly soluble in ethanol and methanol. Insoluble in water. |
| Use | For food, medicine, cosmetics coloring |
CI 75125 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 32030019 |
CI 75125 - Introduction
Open Data Unverified Data
is a natural pigment contained in plants. It is mainly found in the mature fruits of the Solanaceae plant tomato. It is one of the strongest antioxidants currently found in plants in nature. Science has proven that singlet oxygen and oxygen free radicals in the human body are the culprits of attacking the body's own immune system. The effect of lycopene on scavenging free radicals is far better than that of other carotenoids and vitamin E, and its quenching singlet oxygen rate constant is 100 times that of vitamin E. It can effectively prevent and treat various diseases caused by aging and decreased immunity. Therefore, it has attracted the attention of experts around the world.
Last Update：2022-01-01 08:49:10
CI 75125 - Related research
Open Data Unverified Data
- Lycopene (Lycopene) also known as & psi;-carotene, belonging to isoprene compounds, is a kind of carotenoids. Due to the earliest isolated from tomato, so called lycopene. In the past, it has been considered that only those carotenoids which have β-ionone ring and can be converted into vitamin A, such as α-carotene and β-carotene, are related to human nutrition and health, due to the lack of this structure, lycopene does not have the physiological activity of vitamin A, so there is little research on this; However, lycopene has superior physiological function, it not only has the effect of anticancer, but also for the prevention of cardiovascular disease, atherosclerosis and other adult diseases, enhance the body's immune system and anti-aging, etc. are of great significance, is a promising new functional natural pigment.
- lycopene (lycopene) is the main pigment of mature tomato, is a kind of non-oxygen carotenoids. This red crystal was first isolated by Hartsen in 1873 from the mother of the Berry Dioscorea, Tamus communis L.
- in 1910, Willstaller and Escher in the study of lycopene for the first time to determine its molecular formula C40H56, the molecular weight of 536.85. Schunk discovered the difference between this substance and carotene in 1913, and named it lycopene for the first time. So far, the pure product is needle-like deep red crystals. In 1930, Karrer et al. proposed that lycopene is a non cyclic planar polyunsaturated aliphatic hydrocarbon containing 11 conjugated double bonds and 2 non conjugated double bonds in a chemical structural formula, which can form a beta carotene after cyclization. Naturally occurring lycopene is all-trans, but through the high temperature cooking, frying and other processing methods can make lycopene from trans configuration to cis configuration, and the cis configuration in the dried tomato or dried tomato pomace will also have a partial change. The study also showed that the physical and chemical properties of the cis isomer and the trans isomer of lycopene were different. Compared with the trans isomer, the melting point of the cis isomer of lycopene was low, the molar extinction coefficient was small, and the polarity was strong, it is not easy to crystallize, more soluble, and may return to the all-trans state during storage.
Last Update：2022-01-01 08:49:11
CI 75125 - Introduction
Pharmacological effects: It has the effects of anti-oxidation, prevention and inhibition of cancer, cardiovascular protection, anti-ultraviolet radiation, prevention of osteoporosis, lowering blood pressure, and reducing asthma caused by exercise.
Last Update：2022-10-16 17:25:37
CI 75125 - Carotenoids
Open Data Unverified Data
- Lycopene is a very important class of carotenoids, its scavenging singlet oxygen (1O2) oxidation rate constant is 100 times that of vitamin E, is twice that of Beta 2 carotene. Lycopene can effectively prevent prostate cancer, digestive tract cancer, cervical cancer, skin cancer and cardiovascular disease, the inhibition of uterine cancer, lung cancer cells was significantly higher than beta 2 carotene and Alpha 2 carotene. Moreover, lycopene is also a micronutrient associated with aging diseases in serum, which can inhibit aging-related degenerative diseases. Lycopene is very strong in protecting lymphocytes from cell membrane damage or cell death caused by NO2 free radicals, and its ability to scavenge free radicals is also stronger than other carotenoids.
- Lycopene is a red colorant found in tomato, pink grapefruit and palm oil. It is a linear derivative of carotene and has no vitamin A activity.
preparation method of lycopene
1kg of crude tomato powder (containing 180mg of lycopene) and 2L of hexane were placed in an extractor, and homogenized to dissolve lycopene in hexane. Then contact supercritical carbon dioxide, the condition is 30~50 deg C, 2.94MPa. The colorant enters the separator, and about 200g of refined lycopene oil (containing 1370mg/100g of lycopene) is obtained by decompression and separation. The lycopene obtained by this method is colored very bright in oil, orange and almost odorless. At 15 ° C for 1 month, no odor and discoloration occurred.
Last Update：2022-01-01 08:49:12
CI 75125 - Research history
Open Data Unverified Data
lycopene was first isolated by Harlsen in 1873 from Tamus communisL. berries and is a deep red crystalline pigment. In 1875, milldel obtained a crude extract containing lycopene from tomato and called it Solanorubin. Dug2gar in 1913 in the study of the effect of growth conditions on the content of lycopene, it is called the Lycopersicon. Suhunck found that the pigment extracted from tomato had a different absorption spectrum from that of carotene extracted from carrot in 193 and named it Lycopene.
at the beginning of the 20th century, people began to study the basic chemical structure of lycopene.
- IL-1 Statter and Escher first proposed that lycopene is an isomer of carotene with the molecular formula C40H56 in 1901.
- in 1930karrer et al. proposed that the chemical structure of lycopene is an acyclic planar multi-conjugated double bond structure composed of 11 conjugated and 2 non-conjugated carbon-carbon double bonds, and confirmed by Kuhn and Grundmann in 1932.
- since lycopene has no β-Angelica aromatic ring structure and does not have vitamin A activity, it has been studied less.
- in1974b jelke found that eating tomatoes can reduce the occurrence of cervical cancer, colon cancer, esophageal cancer, rectal cancer, gastric cancer and so on.
- in 1989, Mascio et al. found that lycopene quenched singlet oxygen at the highest rate of all carotenoids, including β-carotene.
- in 1991, Camp2bell et al. found that the content of lycopene in the liver of patients with liver cancer was lower than that of normal people.
- 1994 Franceshi et al. found that the occurrence of digestive tract cancer was also related to the intake of lycopene.
These reports have attracted great interest and attention of scientists in various countries in the research and development of physiological functions of lycopene. The physiological functions and extraction methods of lycopene have been reported and introduced in China since 1990.
Last Update：2022-01-01 08:49:13
CI 75125 - Physical properties
Open Data Unverified Data
One of tomato red carotenoid compounds, natural plant pigment, deep red needle-like crystal, melting point 172~173 ℃, insoluble in water, insoluble in methanol, ethanol, cyclohexane and other polar organic solvents, soluble in ether, petroleum ether, hexane, acetone. Soluble in chloroform, carbon disulfide, benzene, oil and so on. There is a strong absorption peak at 472nm, when the molecule changes from the anti structure to the CIS structure, the color becomes lighter, the melting point decreases, the extinction coefficient decreases, and the absorption peak shifts. Natural lycopene is widely found in plants, and the content of mature fruits such as tomato is higher. It can be extracted from mature tomato or prepared by multi-step chemical reaction. It is the main index to measure the quality of processed tomatoes (sauce and juice). General requirements per hundred grams of fresh weight containing lycopene 8mg or more, in order to meet the requirements of processing varieties such as sauce. The content of lycopene in different tomato varieties is not only controlled by genetic factors, but also affected by the external environment. For example, if the temperature exceeds 30 ℃ or below 12 ℃, the lycopene content will be reduced.
Last Update：2022-01-01 08:49:13
CI 75125 - Chemical properties
Open Data Unverified Data
- lycopene is an isomer of carotene, also known as lycopene, fat soluble, mainly exists in mature tomatoes and other fruits, is a component of tomato red pigment, in red tomatoes, lycopene and carotene exist together, the average content of 4.0% ~ 7.8%, is the average content of carotene (0.40% ~ 0.75%) 10 times. The content of these two pigments in tomato gradually increased with the ripening of the fruit, and the content of carotene was the highest when the tomato was ripe, and the content of the fruit was significantly decreased (25% ~ 40%). The production of lycopene is closely related to the temperature, and the optimum temperature is 24. Above 30 ℃, lycopene could not be formed.
- Lycopene is a transition from an inverse structure to a CIS structure in which a conjugated polyunsaturated Olefin is susceptible to oxidative decomposition. These changes can be facilitated by light, heat, acids, bases, and surfactants during extractive separation, processing, and preservation. Sharma and Maguer believe that the decomposition reaction of Lycopene is a pseudo-first-order reaction, indicating that the decomposition of lycopene is affected by many factors. The research report of he et al pointed out that heat treatment can significantly increase the CIS lycopene in tomato juice. Scherliar and Stahl et al. also found that heat treatment can improve the absorption rate of lycopene in tomato juice by the human body.
- In addition, since it does not have a B- azol ketone ring structure, it does not have provitamin activity. Hydrochloric acid has a strong destructive effect on lycopene, while the effect of alkali is not large. Lycopene is relatively stable to alkali and sensitive to oxidation reaction.
Last Update：2022-01-01 08:49:14
CI 75125 - Distribution and metabolism of lycopene
Open Data Unverified Data
- the plant distribution of lycopene is mainly distributed in tomato, watermelon, red grape sleeve fruit and red brown oil, and the content of other vegetables and fruits is relatively low. Among them, the content of lycopene in tomato is the highest, and its content varies with the difference of varieties and maturity. The higher the maturity, the more the content of lycopene.
- mammals cannot synthesize lycopene by themselves and must obtain it from fruits. Lycopene absorption is affected by many factors. Among them, the protein-carotene complex in food, a large amount of soluble dietary fiber if glue, combined cholesterol and resin, iron, zinc and protein deficiency, and intestinal diseases, allergic reactions or parasites may interfere with the absorption of lycopene.
- in the metabolic process of lycopene, some oxidation products of lycopene can also be detected in human serum. Lycopene is the main kind of human tissue in the pill and the highest content of adrenal gland. Human plasma, lycopene accounted for one of the total carotenoids in plasma, prostate accounted. The study found that there was no gender difference in plasma lycopene levels, intake of lycopene can be detected in the feces, but there is a certain relationship with smoking. In addition, with the increase of age, blood lycopene levels will decline.
- in human tissues, liver, adrenal gland and testis had higher levels of lycopene, while lung and kidney had little content. Studies from the United States reported that lycopene levels exceeded B- carotene in almost every tissue except the kidneys. Studies from Germany have reported that B- carotene exceeds lycopene in the liver, adrenal glands and kidneys, with the exception of the testes. It has even been found that the amount of lycopene in human liver is as high as 10 to 55nmol/g of liver tissue, and that of B- carotene is 5.8 to 25nmol/g of liver tissue. The level of lycopene in the skin is slightly higher than that of B- carotene, 0.42 and 0.27nmol/g, respectively, 1.6 and 1.4nmol/g skin tissue, respectively. Although hydrocarbon carotenoids are very lipophilic, the levels in adipose tissue are lower than those in liver or testis, and the total amount of carotenoids in adipose tissue accounts for a large part of the total body, because adipose tissue accounts for about 20% of a person's body weight. The distribution of lycopene in different tissues of rats and monkeys was studied by radioactive labeling, which showed that the liver was the main organ for lycopene accumulation.
Last Update：2022-01-01 08:49:15
CI 75125 - Antioxidants
Open Data Unverified Data
- due to the structure of more conjugated double bonds on the same plane, lycopene has the effect of efficiently quenching singlet oxygen and scavenging free radicals, and its antioxidant activity is the strongest in carotenoids.
- oxygen free radicals are produced in tissues and can react with important macromolecules such as DNA, proteins, carbohydrates and lipids in the body, damaging their functions and causing a series of diseases, such as cancer, cardiovascular disease and aging, lycopene can be broken by singlet oxygen (O2) and scavenging hydrogen peroxide and other effects of disease inhibition.
- lycopene is the strongest carotenoid for quenching singlet oxygen and scavenging free radicals such as hydrogen peroxide. Carotenoids quench singlet oxygen by physical and chemical means. Physical quenching of singlet oxygen mainly undergoes the following process to transfer activation to carotenoids, producing ground state oxygen and activated triplet carotenoids, the rest of the energy is released in the form of heat by rotational vibration with substances such as solvents in the surrounding environment, and the newly generated ground state carotenoids can participate in the next cycle of scavenging singlet oxygen. The ability of carotenoids to scavenge singlet oxygen depends mainly on the number of conjugated double bonds in their molecules-lycopene has a stronger ability to scavenge singlet oxygen than other carotenoids, its rate constant for scavenging singlet oxygen is 100 times that of vitamin E, a commonly used antioxidant, and twice that of B- carotene. It is believed that this increased capacity is associated with its other two double bonds that are not bound. Lycopene can prevent lipid oxidation by quenching singlet oxygen. In addition, it can also react with reactive oxygen species such as hydrogen peroxide and nitrogen dioxide to protect biofilms from free radical damage. Recent studies have shown that lycopene has a very strong ability to protect lymphocytes from cell membrane damage or cell death caused by NO2 free radicals. Its ability to scavenge oxygen free radicals is also stronger than other carotenoids.
- lycopene inhibits the phospholipid metabolism of cancer cells, regulates tumor suppressor genes, reduces the incidence of tumors, and inhibits the proliferation of tumor cancer cells.
Last Update：2022-01-01 08:49:15
CI 75125 - Health care function
Open Data Unverified Data
- the role of lycopene in preventing the occurrence of various diseases is being confirmed, and these physiological functions are related to the free radical scavenging function of lycopene. Preliminary studies have shown that lycopene can reduce the incidence of degenerative diseases such as cardiovascular disease and cancer and has the effect of delaying aging. The function of carotenoids to prevent cancer is being studied, and the role of lycopene has attracted attention. Regular consumption of tomatoes and processed tomatoes was associated with a Incidence Rate reduction in prostate, esophageal and other cancers. Lycopene can inhibit the growth of human endometrial cells and lung cancer cells, and the inhibitory effect of lycopene is the same as 4 times the amount of a-carotene or 10 times the amount of B- carotene. Lycopene can also inhibit the occurrence of breast tumors in animals. In regions where tomato products are frequently taken, such as the Mediterranean region, the incidence of some chronic diseases is low and a positive role for lycopene has been demonstrated. In the consumption of tomato or tomato processing, because lycopene is a fat soluble component, in order to better absorb it and avoid the risk of atherosclerosis, it should be a single unsaturated fatty acid, such as olive oil to cook tomatoes, this allows better absorption and utilization of lycopene. Various forms of tomato products are also under development, such as the development of low-fat, low-heat tomato ice cream.
Last Update：2022-01-01 08:49:16
CI 75125 - Stability
Open Data Unverified Data
- Lycopene is a functional natural pigment with strong physiological activity. Extracting lycopene from tomato peel can fully realize the comprehensive utilization of resources, prevent environmental pollution, and has economic feasibility. For example, waste by-products (Tomato Peel and tomato seeds) from a tomato paste plant can be used.
- lycopene has good stability to heat, and has good stability below 50 ℃.
- acid has little damage to the stability of lycopene, but the influence of alkali is great, and lycopene is relatively stable to acid.
- the reducing agent Ascorbic acid is often used as an antioxidant in canned fruits, fruit juices, vegetables and other foods. However, it can also be a pro-oxidant under certain conditions. It is reported that ascorbic acid is a pro-oxidant for carotene and linolenic acid ester system at low concentration, and this pro-oxidation may be related to the system of ascorbic acid and the presence of oxygen and trace metal ions, therefore, in tomato products or in the use of lycopene, if you want to add ascorbic acid in the products, you should pay attention to the presence of metal ions, ascorbic acid may produce oxygen promoting effect, the optimization method is, together with the use of ascorbic acid, the necessary metal ion chelating agents and other phenolic antioxidants are added.
- the effect of citric acid on the stability of lycopene is greater than that of acetic acid, which is because citric acid is more acidic than acetic acid. Adding two acids of equal concentration, the former can lower the pH value of the solution, only when the pH of the solution is lower than a certain value, it will have a significant impact on the stability of lycopene, so in the production of tomato products or lycopene should pay attention to the control of pH value.
- Fe3 and Cu2 had great influence on the stability of lycopene, and other test Metal Ions had little influence on it.
- lycopene is very unstable to light, especially when it is lost in one day under direct sunlight, and it is well preserved in the dark.
Last Update：2022-01-01 08:49:17
CI 75125 - Chemical properties and uses
Open Data Unverified Data
chemical properties
- One of the carotenoids. Needle-like deep red crystals (precipitated from a mixture of carbon disulfide and ethanol). Melting Point 174 °c. Flammable. Soluble in carbon disulfide (1G/50 m1), boiling ether (1g/3L), n-hexane (1g/14 L,0 C). Soluble in chloroform and benzene. Slightly soluble in ethanol and methanol. Insoluble in water.
- in the plant body is relatively stable, the pure product is easy to oxidize, can absorb oxygen up to 30% (finally up to 41%).
- the content in the mature tomato is more than (0.02g/kg). It is still present in the red pepper, the rose hip, the fruit of the shadow grass, the flesh of the Persimmon, the pumpkin, the fruit of the grapefruit, and one of the red bacteria Shicystis, etc.
purpose
- edible red pigment. For tomato juice products.
- for the prevention and treatment of prostate cancer, breast cancer and digestive tract cancer and other diseases, and can reduce skin cancer, bladder cancer Incidence Rate, but also can strengthen the body, to achieve cosmetic efficacy
- dark red powder or oily liquid. The oil solution was yellow-orange in color. Excellent heat and light resistance. Insoluble in water, soluble in ethanol and oil. The pigment of carotenoids, pure products for the needle-like deep red crystals (from the mixture of carbon disulfide and ethanol precipitation). Melting Point 174 ℃, flammable. Soluble in carbon disulfide (1g/50ml), boiling ether (1g/3L), ethane (1g/14L,0 ℃); Soluble in chloroform and benzene; Slightly soluble in ethanol and methanol; insoluble in water. Uses: The use of red pigment. Its oil resin calls 1%, heat, light stability, and antioxidant capacity and typical tomato flavor, in addition to the use of a variety of tomato products, but also suitable for meat, soup, sauce, candy, snack food and pasta, etc.
- for food, medicine, cosmetics coloring
Last Update：2022-01-01 08:49:18
CI 75125 - Production method
Open Data Unverified Data
Generally, when the natural plant tomato (Lycoper-sicon solanaceae) is mixed with carotene, the mixture is separated by dissolution with benzene containing 1% ethanol. Such as petroleum ether solution, can be obtained by magnesium oxide adsorption. It can also be obtained by oil extraction.
Last Update：2022-01-01 08:49:18
CI 75125 - Safety Information
Open Data Unverified Data
mark of dangerous goods Xi
Hazard code 36/37/38
Safety instructions 26-36/37/39
WGK Germany 3
F 8-10-23
Last Update：2022-01-01 08:49:19
CI 75125 - Reference Information
| FEMA | 4110 | TOMATO LYCOPENE |
| carotenoids | lycopene is a very important class of carotenoids. Its oxidation rate constant for scavenging singlet oxygen (1O2) is 100 times that of vitamin E and twice that of β2 carotene. Lycopene can effectively prevent prostate cancer, digestive tract cancer, cervical cancer, skin cancer and cardiovascular diseases, and its inhibitory effect on uterine cancer and lung cancer cells is significantly higher than β2 carotene and α2 carotene. Moreover, lycopene is also a micronutrient related to aging diseases in serum, which can inhibit aging-related degenerative diseases. Lycopene is very powerful in protecting lymphocytes from cell membrane damage or cell death caused by NO2 free radicals, and its ability to scavenge free radicals is also stronger than other carotenoids. Lycopene is a red colorant in tomatoes, pink grapefruit and palm oil. It is a linear derivative of carotene. It has no vitamin A activity and is used as an edible colorant. Figure 1 shows lycopene. preparation method of lycopene: crude tomato powder 1kg (containing lycopene 180mg) and hexane 2L are put into an extractor for homogenization treatment to dissolve lycopene in hexane. Then contact supercritical carbon dioxide under the conditions of 30~50 ℃ and 2.94MPa. The colorant enters the separator and is separated under reduced pressure to obtain about 200g of refined lycopene oil (containing 1370mg/100g of lycopene). The lycopene obtained from this method is very bright in petroleum, orange, and almost odorless. After being placed at 15 ℃ for 1 month, no peculiar smell and discoloration occurred. |
| Research history | Lycopene was first separated by Harlsen from Tamus communisL. berries in 1873 and is dark red crystal pigment. In 1875, Millardel obtained a crude extract containing tomato red from tomatoes, which was called Solanorubin. In 1913, Dug2gar called it Lycopersicon when studying the effect of growth conditions on lycopene content. In 1903, Suhunck discovered that the pigment extracted from tomatoes had a different absorption spectrum from the carotene extracted from carrots, and named it Lycopene. At the beginning of the 20th century, people began to study the basic chemical structure of lycopene. In 1901, illstatter and Escher first proposed that lycopene is an isomer of carotene, and its molecular formula is C40H56. In 1930, Karrer et al. proposed that the chemical structural formula of lycopene is an acyclic planar polyconjugated double bond structure composed of 11 conjugated and 2 non-conjugated carbon-carbon double bonds. It was confirmed by Kuhn and Grundmann in 1932. Since lycopene has no β-Zhi Xiang ring structure and does not have vitamin A original activity, there are few studies on it. In 1974, B jelke found that eating tomatoes can reduce the occurrence of cervical cancer, colon cancer, esophageal cancer, rectal cancer, and gastric cancer. In 1989, Mascio et al. found that among all carotenoids including β-carotene, lycopene had the highest rate of quenching singlet oxygen. In 1991, Camp2bell and others found that the lycopene content in the liver of liver cancer patients was lower than that of normal people. In 1994, Franceshi and other studies found that the occurrence of digestive tract cancer is also related to the intake of lycopene. after the publication of these reports, scientists from various countries have attracted great interest and attention in the research and development of physiological functions of lycopene. Since 1990, there have been reports and introductions on the physiological functions and extraction methods of lycopene in China. |
| physical properties | one of the tomato red carotenoid compounds, natural plant pigment, deep red needle crystal, melting point 172~173 ℃, insoluble in water, insoluble in methanol, ethanol, cyclohexane and other polar organic solvents, soluble in ether, petroleum ether, hexane, acetone. Easily soluble in chloroform, carbon disulfide, benzene, grease, etc. There is a strong absorption peak at 472nm. When the molecule changes from antistructure to cis-structure, the color becomes lighter, the melting point decreases, the extinction coefficient decreases, and the absorption peak shifts. Natural lycopene is widely found in plants, and the content of mature fruits such as tomatoes is higher. It can be extracted from mature tomatoes or made by multi-step chemical reaction. It is the main index to measure the quality of processed tomatoes (sauce, juice). Generally, it is required to contain more than 8mg of lycopene per 100 grams of fresh weight to meet the requirements of processing varieties such as sauce making and cans. The lycopene content of different tomato varieties is not only controlled by genetic factors, but also affected by the external environment. If the temperature exceeds 30 ℃ or below 12 ℃, the lycopene content will be reduced. |
| distribution and metabolism of lycopene | plant distribution of lycopene is mainly distributed in tomatoes, watermelons, fruits of red grape sleeves and red brown oil, while the content of other vegetables and fruits is relatively low. Among them, the content of lycopene in tomato is the highest, and its content varies with the difference of variety and maturity. The higher the maturity, the more lycopene content. Mammals cannot synthesize lycopene by themselves, they must obtain it from fruits. Lycopene absorption is affected by many factors. Among them, the protein-carotene complex in food, a large amount of soluble dietary fiber if gum, combined cholesterol and resin, iron deficiency, zinc and protein, as well as intestinal diseases, allergic reactions or parasites may interfere with lycopene Absorption. During the metabolism of lycopene, some oxidation products of lycopene can also be detected in human serum. Lycopene is the main type of hubsu in tissues, and the content of human gao pills and adrenal glands is the highest. In human plasma, lycopene accounts for one of the total carotenoids in plasma, and in the prostate. Studies have found that there is no gender difference in plasma lycopene levels. The intake of lycopene can be detected in feces, but it has a certain relationship with smoking. In addition, with age, the level of lycopene in the blood will decrease. in human tissues, the levels of lycopene in liver, adrenal gland and testis are higher, while the content in lung and kidney is very small. Studies from the United States reported that lycopene levels in almost every tissue exceeded B- carotene, except for the kidneys. Studies from Germany have reported that B- carotene exceeds lycopene in the liver, adrenal glands and kidneys, with the exception of the testis. It was even found that the amount of lycopene in human liver was as high as 10 to 55nmol/g of liver tissue and B- carotene was 5.8 to 25nmol/g of liver tissue. The level of lycopene in skin is slightly higher than that of B- carotene, which is 0.42 and 0.27nmol/g respectively. It is also found that there are high levels of lycopene and B- carotene in skin, which are 1.6 and 1.4nmol/g respectively. Although hydrocarbon carotenoids are extremely lipophilic, their levels in adipose tissue are lower than those in liver or testis, while the total amount of adipose carotenoids accounts for a large part of the body's total, because adipose tissue accounts for about 20% of human body weight. Radiolabelling was used to study the distribution of lycopene in different tissues of rats and monkeys, indicating that the liver is the main organ for lycopene accumulation. |
| Antioxidant | Due to the structure of more conjugated double bonds on the same plane, lycopene has the effect of efficiently quenching singlet oxygen and scavenging free radicals. Its antioxidant properties are the strongest among carotenoids. Oxygen free radicals are produced in tissues and can react with important macromolecular substances such as DNA, proteins, carbohydrates and lipids in the body, damage their functions, and cause a series of diseases, such as cancer, cardiovascular diseases and aging. Lycopene can inhibit diseases by destroying singlet oxygen (O2) and scavenging hydrogen peroxide. Lycopene is the carotenoid with the strongest ability to quench singlet oxygen and scavenge free radicals such as hydrogen peroxide. Carotenoids quench singlet oxygen physically and chemically. Physical quenching of singlet oxygen mainly undergoes the following process to transfer activation to carotenoids, producing ground state oxygen and activated triplet carotenoids, and the rest of the energy passes through the solvent in the surrounding environment in the form of heat. The rotating vibration between other substances is released, and the re-generated ground carotenoids can participate in the next cycle of clearing singlet oxygen. The ability of carotenoids to remove singlet oxygen mainly depends on the number of conjugated double bonds in their molecules-lycopene has a stronger ability to remove singlet oxygen than other carotenoids, and its removal singlet The rate constant of oxygen is 100 times that of the currently commonly used antioxidant vitamin E and twice that of B- carotene. Some people think that this increased ability is related to its other 2 unbound double bonds. Lycopene can prevent lipid oxidation by quenching singlet oxygen. In addition, it can also react with active oxygen fragments such as hydrogen peroxide and nitrogen dioxide to protect biofilms from free radical damage. The latest research shows that lycopene has a very strong ability to protect lymphocytes from cell membrane damage or cell death caused by NO2 free radicals. Its ability to scavenge oxygen free radicals is also stronger than other carotenoids. Through antioxidant lycopene, it inhibits phospholipid metabolism of cancer cells, regulates tumor suppressor genes, reduces the incidence of tumors, and inhibits the proliferation of tumor cells. |
| health care function | lycopene's role in preventing the occurrence of various diseases is being affirmed. these physiological functions are related to lycopene's free radical scavenging function. Preliminary studies have shown that lycopene can reduce the occurrence of degenerative diseases such as cardiovascular diseases and cancer and has the effect of delaying aging. The function of carotenoids in preventing cancer is being studied, and the role of lycopene has attracted attention. Eating tomatoes and processed tomato products can reduce the incidence of prostate cancer, esophageal cancer and other cancers. Lycopene can inhibit the growth of human endometrial cells and lung cancer cells. The inhibitory effect of lycopene is the same as that of 4 times the amount of a-carotene or 10 times the amount of B- carotene. Lycopene can also inhibit the occurrence of breast tumors in animals. In areas where tomato products are frequently taken, such as the Mediterranean region, the incidence of some chronic diseases is relatively low, and lycopene has been confirmed to have a positive effect on it. When eating tomatoes or processed tomato products, since lycopene is a fat-soluble ingredient, in order to better absorb it and avoid the risk of atherosclerosis, monounsaturated fatty acids, such as olive oil, should be used to cook tomatoes. This can better absorb and utilize lycopene. Various forms of tomato products are also under development, such as the development of low-fat, low-heat tomato ice cream. |
| stability | (1) lycopene is a functional natural pigment with strong physiological activity. Extracting lycopene from tomato peel can fully realize the comprehensive utilization of resources and prevent environmental pollution, which is economically feasible. For example, the by-products (tomato peel and tomato seeds) discarded from the tomato sauce factory can be used. (2) lycopene has good stability to heat, and the stability below 50 ℃ is better. (3) acid has little damage to lycopene stability, but alkali has great influence. lycopene is relatively stable to acid. (4) reducing agent ascorbic acid is often used as an antioxidant in canned fruits, fruit juices, vegetables and other foods. But under certain conditions, it can also become a pro-oxidant. According to reports, ascorbic acid is a pro-oxidant for carotene and linolenic acid ester systems at low concentrations. This pro-oxidation effect may be related to the system in which ascorbic acid is located and the presence of oxygen and trace metal ions. In tomato products or when using lycopene, if you want to add ascorbic acid to the products, you should pay attention to the presence of metal ions. It may be that ascorbic acid produces oxygen-promoting effects. The optimized treatment method is, while using ascorbic acid, add necessary metal ion chelating agents and other phenolic antioxidants. (5) sour agent citric acid has a greater effect on the stability of lycopene than acetic acid. this is because citric acid is more acidic than acetic acid. adding two kinds of acids with equal concentration, the former can better reduce the pH value of the solution. only when the pH value of the solution is lower than a certain value, it will have a significant impact on the stability of lycopene. therefore, attention should be paid to controlling the pH value in the production of tomato products or lycopene. (6) Fe3 and Cu2 have great influence on the stability of lycopene, while other experimental metal ions have little influence on it. (7) lycopene is very unstable to light, especially when it is lost in the next day under direct sunlight, and it is better preserved in the dark. |
| use | edible red pigment. For tomato juice products. It is used to prevent and treat prostate cancer, breast cancer and digestive tract cancer, and can reduce the incidence of skin cancer and bladder cancer. At the same time, it can also strengthen the body and achieve cosmetic effects. Dark red powder or oily liquid. The oil solution is yellow-orange. Excellent heat resistance and light resistance. Insoluble in water, soluble in ethanol and grease. Its pigment belongs to carotene, and the pure product is needle-like dark red crystals (precipitated from the mixture of carbon disulfide and ethanol). Melting point 174 ℃, combustible. Soluble in carbon disulfide (1g/50ml), boiling ether (1g/3L), n-ethane (1g/14L,0 ℃); Soluble in chloroform and benzene; Slightly soluble in ethanol and methanol; Insoluble in water. Use: Use red pigment. Its oleoresin is 1%, stable to heat and light, and has antioxidant capacity and typical tomato flavor. In addition to being used in various tomato products, it is also suitable for meat, soup, sauce, candy, snacks and noodles. An antioxidant micronutrient in tomatoes that has been linked to a reduced risk of cancer and cardiovascular disease. Up-regulation of gap junction protein 43 promotes intercellular gap junction communication and inhibits cancer cell proliferation in culture. Inhibit cholesterol synthesis and promote low density lipoprotein degradation. for coloring food, medicine and cosmetics |
| production method | when the natural plant tomato (Lycoper-sicon solanaceae lanaceae) is mixed with carotene, it is dissolved and separated with benzene containing 1% ethanol. If it is a petroleum ether solution, it can be obtained by adsorption of magnesium oxide. It can also be obtained by oil extraction. |
Last Update：2024-04-09 02:00:09
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