122871-99-2
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione
CAS: 472-61-7;122871-99-2
Molecular Formula: C40H52O4
122871-99-2 - Names and Identifiers
| Name | 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione |
| Synonyms | AXN ASTAXANTHIN Astaxanthin Natural astaxanthin HAEMATOCOCCUS PLUVIALIS 3,3-DIHYDROXY-B,B-CAROTENE-4,4-DIONE 3,3'-DIHYDROXY-B,B-CAROTENE-4,4'-DIONE 3,3'-DIHYDROXY-BETA,BETA-CAROTENE-4,4'-DIONE 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione (3S,3'S)-3,3'-dihydroxy-beta,beta-carotene-4,4'-dione (3S,3'S)-3,3'-Dihydroxy-.beta.,.beta.-carotene-4,4'-dione (9cis,9'cis,13cis,13'cis,15cis)-3,3'-dihydroxy-beta,beta-carotene-4,4'-dione |
| CAS | 472-61-7 122871-99-2 |
| EINECS | 207-451-4 |
| InChI | InChI=1/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11-,17-13+,18-14+,23-21+,24-22+,27-15-,28-16-,29-19-,30-20- |
| InChIKey | MQZIGYBFDRPAKN-SODZLZBXSA-N |
122871-99-2 - Physico-chemical Properties
| Molecular Formula | C40H52O4 |
| Molar Mass | 596.85 |
| Density | 0.9980 (rough estimate) |
| Melting Point | 215-216 °C |
| Boling Point | 568.55°C (rough estimate) |
| Flash Point | 435.8°C |
| Solubility | DMSO: 1 mg/mL |
| Vapor Presure | 1.14E-27mmHg at 25°C |
| Appearance | Red powder |
| Color | , pink to very dark purple |
| pKa | 12.33±0.70(Predicted) |
| Storage Condition | -20°C |
| Stability | Light Sensitive |
| Refractive Index | 1.4760 (estimate) |
| MDL | MFCD00672621 |
122871-99-2 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29339990 |
122871-99-2 - Reference
| Reference Show more | 1. Zhang Lili, Gao Jing, Wei Yuanyi, et al. Extraction of astaxanthin by LCST ionic liquid-salt aqueous two-phase system [J]. Chinese Journal of Food Science 2020 v.20(04):176-184. 2. Talking about Jia Yu. Effects of different cooking methods on astaxanthin content in Antarctic krill powder [J]. Anhui Agricultural Sciences 2019 47(01):198-201. 3. Wang Baby Zhang Yamin Cai Shulin, etc. Optimization of ethanol extraction of astaxanthin from Haematococcus pluvialis by response surface methodology [J]. Food Science and Technology 2017 042(010):239-243. 4. Feng Xingbiao, Li Guangwei, Chen Danyang, et al. Expression of β-carotene ketolase gene in Chlorella vulgaris to increase the amount of Astaxanthin [J]. Journal of Hefei University of Technology: Natural Science Edition, 2019, 42(02):267-272. 5. Ma Tiantian, Ouyang Jie, Tan Jia-yu, et al. Effects of crushing methods on drying characteristics and quality of Antarctic krill [J]. Science and Technology of food industry, 2019, 40(10):43-48. 6. Chen Suqin, Li Ming Jiang, Wu Feng, etc. Effects of astaxanthin on collagen synthesis induced by Ang Ⅱ in cardiac fibroblasts [J]. Journal of Medical Research, 2018. 7. Hu Wang, Wen-Hua Li, Niudandan, et al. Protective effect of astaxanthin on contrast-induced acute kidney injury in rats and its effect on SIRT1-P53 pathway [J]. Journal of Medical Research, 2018, 47(001):79-84. 8. Luo Yan, Shen Zilong, Ren Jianwu. Improvement effect and mechanism of astaxanthin on aging of Caenorhabditis elegans [J]. Science and Technology of food industry, 2017, 038(022):22-25. 9. [IF = 4.098] Libing Lu et al."Structural characterization of astaxanthin aggregates as disclosed by analysis and simulation of optical spectra." Spectrochim Acta A. Oct;185:85 10. Li Mu-Yang et al. [IF = 2.235]., immune-related gene expression, and disease resistance against in Channa argus."Aquacult Int. 2019 Jun;27(3):735-746 11. [IF=7.514] Litao Wang et al."Optimized extraction of astaxanthin from shrimp shells treated by biological enzyme and its separation and purification using macroporous resin."Food Chem. 2021 Nov;363:130369 12. [IF=7.086] Mu-Yang Li et al."Effect of sub-chronic exposure to selenium and astaxanthin on Channa argus: Bioaccumulation, oxidative stress and inflammatory response."Chemosphere. 2020 Apr;244:125546 13. [IF=5.118] Óscar Martínez-Álvarez et al."Recent Advances in Astaxanthin Micro/Nanoencapsulation to Improve Its Stability and Functionality as a Food Ingredient."Mar Drugs. 2020 Aug;18(8):406 14. [IF=4.411] Mengdan Qiang et al."Effect of Membrane Surface Modification Using Chitosan Hydrochloride and Lactoferrin on the Properties of Astaxanthin-Loaded Liposomes."Molecules. 2020 Jan;25(3):610 15. [IF=4.242] Mu-Yang Li et al."Effects of dietary astaxanthin on lipopolysaccharide-induced oxidative stress, immune responses and glucocorticoid receptor (GR)-related gene expression in Channa argus."Aquaculture. 2020 Feb;517:734816 16. [IF=2.082] Xin-Ming Zhu et al."Effects of dietary astaxanthin on growth, blood biochemistry, antioxidant, immune and inflammatory response in lipopolysaccharide-challenged Channa argus."Aquac Res. 2020 May;51(5):1980-1991 17. [IF=6.475] Chunjun Li et al."Colon and gut microbiota greatly affect the absorption and utilization of astaxanthin derived from Haematococcus pluvialis."FOOD RESEARCH INTERNATIONAL. 2022 Jun;156:111324 |
122871-99-2 - Reference Information
| introduction | astaxanthin is a ketone or carotenoid with pink color, fat soluble, insoluble in water and soluble in organic solvents. It is widely found in the biological world, especially in the feathers of aquatic animals such as shrimp, crabs, fish and birds, and plays a role in color development. Astaxanthin is a non-vitamin A source of carotenoids that cannot be converted into vitamin A in animals. Astaxanthin is a fat-soluble and water-soluble pigment that exists in marine organisms such as shrimp, crab, salmon, and algae. The human body cannot synthesize astaxanthin by itself. It is the strongest antioxidant in nature. Its antioxidant activity is 550 times that of vitamin E and 10 times that of β-carotene, so it is called "the king of antioxidant"! |
| source | 1. synthetic astaxanthin is the end point of carotenoid synthesis. B carotene needs to add 2 hydroxyl groups and 2 ketone groups to convert into astaxanthin, which is difficult to synthesize artificially. Astaxanthin has 3s.3 'S, 3R a 3'S, 3R,3'R (also known as L-R, meso-R, D-R) 3 isomers, of which synthetic astaxanthin is a mixture of 3 structures and has very little antioxidant activity. Biological origin of natural astaxanthin mainly exists in algae, yeast, salmon, trout, shrimp, etc. Astaxanthin of biological origin is safe to use, environmentally friendly, and has broad prospects for development. At present, natural astaxanthin is mainly produced by microbial fermentation. The microorganisms that can produce astaxanthin include: Faff yeast of the fungus Basidiomycetes, two strains of bacteria that assimilate hydrocarbons and green algae that grow in nitrogen-deficient environments. |
| physiological functions and effects | astaxanthin is a chain-breaking antioxidant with strong antioxidant capacity, which can remove NO2, sulfide, disulfide, etc., can also reduce lipid peroxidation and effectively inhibit lipid peroxidation astaxanthin caused by free radicals. According to reports, this product has many physiological effects such as inhibiting tumor occurrence, enhancing immunity, and scavenging free radicals in the body. It has a good therapeutic effect on skin cancer caused by ultraviolet rays, and also has a preventive effect on eye diseases caused by diabetes. It has broad application prospects in health products, medicine, cosmetics, food additives and aquaculture. |
| application field | currently astaxanthin is mainly used as a functional pigment in aquaculture, food, cosmetics and other fields. it is mainly used as a feed additive for fish, shrimps and crabs and other crustaceans and poultry to improve the reproductive capacity and survival rate of livestock, poultry and fish, improve health conditions and optimize body color and meat quality. Natural astaxanthin has been used as a food additive for food coloring, preservation and nutrition enhancement. Studies have shown that astaxanthin helps keep trout slices fresh. In recent years, with the continuous deepening of astaxanthin biological function research and pharmacological efficacy experiments, astaxanthin has attracted great attention from the scientific community due to its effects in the prevention and treatment of cardiovascular diseases, cancer, metabolic syndrome, diabetes, neurodegenerative diseases, ophthalmic diseases, skin diseases and other diseases, indicating that astaxanthin has great potential application value and broad development prospects in the fields of medicine and health products. |
| Biological activity | 1. Antioxidant activity Astaxanthin is a powerful quencher of singlet oxygen, which can scavenge oxygen free radicals and is a powerful antioxidant. By comparing the effects of astaxanthin, lutein, zeaxanthin, B- carotene and lycopene on the concentration of membrane lipid hydrogen peroxide under the action of polyunsaturated fatty acids, non-polar carotenoids, such as lycopene and B- carotene, can increase the level of lipid peroxide 85% and promote the damage of oxidant to cell lipid bilayer, while astaxanthin can reduce the level of lipid peroxide by 40%. 2. Anti-inflammatory activity Astaxanthin has a strong antioxidant effect, and can play an indirect anti-inflammatory effect by regulating the balance between free radicals and antioxidants. Astaxanthin can significantly reduce the level of DNA damage markers and reduce the concentration of plasma C- reactive protein, which confirms the anti-inflammatory effect of astaxanthin on human body. 3. Prevention of atherosclerosis-related diseases Oxidative stress and inflammation are important pathophysiological features of atherosclerotic heart disease, and the strong antioxidant and anti-inflammatory activities of astaxanthin also suggest its potential anti-atherosclerosis effect. Oxidation of low density lipoprotein (LDL) is an important cause of arteriosclerosis, while high density lipoprotein (highdensitylipoprotein,HDL) is negatively correlated with the risk of coronary heart disease. High level HDL can prevent atherosclerosis. Studies have shown that astaxanthin can significantly increase HDL and reduce LDL levels, so astaxanthin may have a certain preventive effect on arteriosclerosis and coronary atherosclerotic heart disease. Anticancer activity astaxanthin can inhibit the growth of breast cancer, while other carotenoids such as B. carotene and canthaxanthin do not have this function. In a word, more and more studies have shown that astaxanthin has anti-cancer and anti-cancer effects, which are mainly reflected in astaxanthin's prevention of tumor occurrence, inhibition of tumor cell proliferation, promotion of tumor cell apoptosis, inhibition of tumor metastasis, enhancement of immunity, increase of cell-to-cell communication, etc. 5. Enhance immune function. The cell membrane contains polyunsaturated fatty acids, which is prone to lipid peroxidation, which leads to changes in the fluidity and permeability of the cell membrane, and ultimately changes the structure and function of the cell. Astaxanthin is unique The molecular structure can be inserted into the lipid bilayer, so compared with B carotene and vitamin C, it can better inhibit lipid peroxidation on the cell membrane and protect the structure of the cell membrane. Immune cells are very sensitive to free radical damage. Free radicals can promote the degradation of macrophage cell membrane and damage its phagocytic function. Antioxidants, especially astaxanthin, can protect the immune system from free radical damage. |
| synthesis method | a method for separating and purifying astaxanthin from Fife yeast includes the following steps: step 1. breaking the wall of Fife yeast: dimethyl sulfoxide is used to break the wall of Fife yeast. the wall breaking conditions are as follows: the ratio of thallus and dimethyl sulfoxide is 1/2 according to the mass volume ratio, I .e. g/ml, at a temperature of 55 ℃, breaking the wall for 5min; Step 2. acetone crude astaxanthin: after breaking the wall, acetone is used to extract astaxanthin according to the material-liquid ratio of 1:15, the material-liquid ratio is the mass-volume ratio of Fife yeast body and acetone, I .e. g/ml, extract twice, combine the extract solution, and remove acetone by rotating evaporation at low temperature. The residual component is astaxanthin crude extract dissolved by dimethyl sulfoxide, and the residual component is astaxanthin primary crude extract; step 3. degreasing and removing low-polar carotenoids: use petroleum ether to extract the first crude extract of astaxanthin, and the extraction ratio is the first crude extract of astaxanthin: the volume ratio of petroleum ether is 1:2, and the extraction times are 2. Discard the upper petroleum ether, collect the lower solution, and the lower solution is the second crude extract of astaxanthin; step 4. to remove dimethyl sulfoxide: the secondary crude extract of astaxanthin and the saturated sodium chloride aqueous solution pre-cooled to 4 ℃ are mixed in a volume ratio of 1:3.5, and the mixed solution is extracted with ethyl acetate, and the amount of ethyl acetate is 3 times the volume of the secondary crude extract of astaxanthin; collect the ethyl acetate phase, rotate and evaporate to dry at low temperature to prepare a higher purity astaxanthin powder; step 5. crystallization: add the astaxanthin powder prepared in step four to dissolve with dichloromethane, after dissolving astaxanthin powder, add methanol to the solution until crystallization is precipitated, let stand, dichloromethane volatilizes naturally, causing astaxanthin crystals to precipitate; Under the condition of centrifugation at 4 ℃ and 9961 ×g, centrifuge for 10min, and collect the bottom crystal to be astaxanthin. |
| preparation | currently, methods for preparing astaxanthin at home and abroad can be divided into two categories: chemical synthesis and biosynthesis. Chemically synthesized astaxanthin is a mixture of three structures: left-handed: right-handed (1:2:1). Chemically synthesized astaxanthin is mainly used as an industrial dye, but it is not allowed to be used in the fields of food and medicine. Biosynthetic astaxanthin is allowed to be used in food and medicine. Some microalgae, fungi, bacteria and specific kinds of plants in nature have the ability to synthesize astaxanthin. Synthetic L-astaxanthin accounts for more than 90% of the total astaxanthin. The chemical synthesis of astaxanthin is divided into total synthesis and semi-synthesis. Astaxanthin total synthesis method uses chemical raw materials as raw materials to obtain astaxanthin through chemical synthesis reaction. The semi-synthetic method is a method of preparing astaxanthin using carotenoids such as horaxanthin, lutein and zeaxanthin as raw materials. |
| product characteristics | shrimp flavin is a red carotenoid found in crayfish shells, oysters and salmon. it can be combined with protein in the body and is blue and blue. It has the effects of anti-oxidation, anti-aging, anti-tumor, and prevention of cardiovascular and cerebrovascular diseases. Astaxanthin is the most widely distributed lutein in the animal kingdom. It is pink and has a unique coloring function. It can also promote the production of antibodies and enhance the immunity of animals; in terms of antioxidant and scavenging free radicals, Its ability is stronger than β-carotene (10 times). It is water-soluble and lipophilic, and is easily soluble in organic solvents such as carbon disulfide, acetone, benzene and chloroform. Astaxanthin is a kind of carotenoid additive with great potential, which has broad prospects in food, feed, cosmetics, medicine and other fields. Astaxanthin-rich foods include marine plants, red red ball microalgae, red Fife yeast, wild salmon, salmon, shrimp, sockeye salmon, rainbow trout and other seafood. Astaxanthin can bring many health benefits, but not everyone can get enough, which is also the problem. |
| natural astaxanthin | natural astaxanthin, also known as astaxanthin, is an extremely precious healthy raw material, which can be used to develop natural and healthy products that enhance immunity, antioxidant, anti-inflammatory, eye and brain health, and regulate blood lipids. At present, it is mainly used as a raw material for human advanced health food and medicine; aquaculture (currently mainly salmon, trout and salmon), feed additives for poultry breeding; cosmetic additives. It can significantly improve the body's immunity. Because it can combine with skeletal muscle non-specific, it can effectively remove free radicals generated by exercise in muscle cells and strengthen aerobic metabolism, so it has a significant anti-fatigue effect. It is the only carotenoid that can pass through the blood-brain barrier. It has a real anti-aging effect. Effective antioxidant is the basis of all beauty activities. Due to its super antioxidant effect, it can effectively remove wrinkles and anti-aging, Sun protection and whitening and removal of chloasma caused by age have good effects in preventing and treating "age-related macular degeneration" and improving retinal function. The above have been clearly confirmed in the United States. The stability and antioxidant activity of synthetic astaxanthin are also lower than that of natural astaxanthin. Because the hydroxyl group (-OH) at both ends of astaxanthin molecule can be esterified, its stability is different. Natural astaxanthin exists in more than 90% esterified form, so it is relatively stable. Synthetic astaxanthin exists in a free state, so the stability is different, and it must be embedded to be stable. Synthetic astaxanthin has only about 1/4 left-handed structure, so its antioxidant activity is only about 1/4 of natural. |
| production process | a method for producing chitin, astaxanthin, protein, calcium powder and biological fertilizer from shrimp shells. the production process is as follows: 1. clean the shrimp shells and mechanically crush them to 5-10 mesh. 2. add water with a weight ratio of 1: 1-2 to the crushed shrimp shell, and add protease for enzymatic hydrolysis. According to different varieties of shrimp shells, the enzymolysis temperature is 30-70 ℃, the PH value is 4-8, the time is 2-6 hours, and the addition of protease accounts for 0.4%-1% of the total weight of shrimp shells. 3. After enzymolysis, heat up to 70-100 ℃ to kill enzyme bacteria, and then cool down. 4. After killing enzyme bacteria, add organic solvent for extraction. The weight ratio of organic solvent to shrimp shell is 1 ∶ 1-2. Fully sealed and stirred for 6-12 hours before cooling. 5. After full reaction, separate into shrimp liquid and shrimp solid. 6. Shrimp liquid is separated into hydrolysate and organic liquid. |
| consumption | ≤ 0.8g/day |
| applicable food category | the scope of use does not include infant food. |
| approval date | 2010-10-29 |
| Announcement No. | Ministry of Health No. 17, 2010 |
| announcement title | announcement on approval of new resource foods such as red Chlorella pluquis |
| Character | Red or crimson powder |
| Protein content | ≥ 15% |
| Total astaxanthin content (in terms of all-trans astaxanthin) | ≥ 1.5% |
| All-trans astaxanthin content | ≥ 0.8% |
| Moisture | ≤ 10% |
| Ash | ≤ 15% |
| use | natural astaxanthin, also known as astaxanthin, is an extremely precious healthy raw material, which can be used to develop natural and healthy products that enhance immunity, antioxidant, anti-inflammatory, eye and brain health, and regulate blood lipids. At present, it is mainly used as a raw material for human advanced health food and medicine; aquaculture (currently mainly salmon, trout and salmon), feed additives for poultry breeding; cosmetic additives. It can significantly improve the body's immunity. Because it can combine with skeletal muscle non-specific, it can effectively remove free radicals generated by exercise in muscle cells and strengthen aerobic metabolism, so it has a significant anti-fatigue effect. It is the only carotenoid that can pass through the blood-brain barrier. It has a real anti-aging effect. Effective antioxidant is the basis of all cosmetic activities. Due to its super antioxidant effect, there can be astaxanthin It is found in seaweed, red yeast and many plant and animal sources? Powerful carotenoid antioxidants. Animal tests have shown that it can reduce blood sugar? and improve several indicators of diabetic metabolic syndrome. Can improve the blood flow and vascular tension of the high blood group model. In vitro studies have shown that it upregulates gap junction protein? 43, which can be used for chemical cancer prevention. |
| 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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