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CAS NO.67604-48-2
medical grade(1-50)Kilogrammedical grade(50-500)Kilogram
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Name | (+|-)-naringenin |
Synonyms | Naringenin -)-Naringenin TIMTEC-BB SBB006461 4,5,7-Trihydroxyflavone 4',5,7-Trihydroxyflavanone 5,7,4'-TRIHYDROXYFLAVANONE 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE 5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one |
CAS | 93602-28-9 67604-48-2 |
EINECS | 266-769-1 |
Molecular Formula | C15H12O5 |
Molar Mass | 272.25 |
Melting Point | 247-250°C(lit.) |
Boling Point | 577.5°Cat760mmHg |
Solubility | Soluble in ethanol, ether and benzene, almost insoluble in water. |
Appearance | White needle crystal |
Storage Condition | -20℃ |
MDL | MFCD00006844 |
Physical and Chemical Properties | Naringenin (4 ',5, 7-trihydroxydihydroflavone) is an aglycone obtained by hydrolyzing naringin from one molecule of glucose and rhamnose Figure 1). It is a white needle-like crystal at room temperature. The storage condition is generally a cool and dry environment with a melting point of 247~250 ℃. Because its molecule contains benzene ring, hydroxyl group, carbonyl group and other functional groups, it has absorption in the ultraviolet region. The ultraviolet spectrum of anhydrous ethanol has the maximum absorption at 288 nm. Mass spectrometry (MRM) detection shows that the ion pair is 273.4/153.. Naringenin is soluble in ethanol, ether and benzene, but almost insoluble in water. The reaction of magnesium hydrochloride powder was cherry red, the reaction of sodium tetrahydroborate was reddish purple, and the reaction of molish was negative. Fat-soluble and water-soluble are not ideal. By introducing fat-soluble or water-soluble groups to modify its structure, it can improve its fat-soluble or water-soluble, thereby improving biological profitability. Its structural modification mainly includes alkylation, acylation, sulfonation, glycosidation and formation of metal complexes of hydroxyl groups. |
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 - Wear suitable protective clothing. |
WGK Germany | 3 |
, A monomer that is a dihydroflavonoid with the molecular formula C15H12O5. Naringin is rich in sources, mainly in the form of glycosides (naringin) widely exists in the peel and pulp of tomato, grapefruit, orange, orange and other Rutaceae plants, but also the fructus aurantii, fructus aurantii immaturus, rhizoma drynariae, citrus is one of the main active ingredients of traditional Chinese medicine, is the domestic and foreign pharmacological research shows that Naringenin has antibacterial, anti-inflammatory, antioxidant, anti-fibrosis, anticancer, antitumor, antiviral, antiarrhythmic, antitussive, prevention of atherosclerosis, immune regulation of fat metabolism, anti-aging, protection of liver function and estrogen-like and other pharmacological activities, a large number of studies have shown that naringenin and its glycosides have a wide range of biological activity, with the promotion of gastrointestinal peristalsis, spasmolysis, antioxidant, anti-tumor, anti-bacterial, anti-atherosclerosis, hypolipidemic, sedative, analgesic, regulating blood sugar and other effects.
Naringenin is well absorbed orally and widely distributed in the body. It is mainly excreted through opening, dehydrogenation, pyrolysis and other reactions to produce P-hydroxyphenylalanine, P-hydroxycinnamic acid and other metabolites, however, its glycoside is poorly absorbed than naringin orally, and most of them are metabolized by deglycosylation of intestinal flora into naringenin by passive diffusion through intestinal wall. Can be developed and applied to medicine, food and other fields. Although Naringenin has a wide range of pharmacological activities, its clinical application is limited because of its poor water solubility and fat solubility, easy oxidation, poor absorption in vivo, low oral bioavailability and other shortcomings. At present, there is no naringenin-related products on the market. Domestic researchers have tried to improve the bioavailability of naringenin by connecting water-soluble groups or making solid dispersions, inclusion compounds, self-microemulsions and other dosage forms, with a view to the early development of new products can be listed.
figure: pomelo peel
Overview | |
extraction and separation | naringin generally exists in nature in the form of naringin in Rosaceae, Rutaceae, citrus plants, the content is very low, but its source is extensive, and it has certain resource advantages in the research and application of drugs. In recent years, naringenin extraction, separation and purification process has made some progress, using supercritical CO2 extraction technology from peach leaves extract naringenin, the average yield of up to 2.18%, good quality naringenin extract products were obtained, but the extract contains a lot of chlorophyll, resulting in product appearance color is green, and pure naringenin products have a certain gap with light yellow, in order to improve product quality, the purification process of naringenin needs further development. In addition, the use of organic solvent extraction method, the first Peach leaf powder for crude extraction to remove a large number of chlorophyll, and then the peach leaf powder for secondary extraction to extract naringenin the extraction process can not only get chlorophyll products, at the same time can obtain high purity naringenin products, measured by spectrophotometry naringenin average yield was 5.25%. Domestic scholars also use 70% ethanol to extract high purity naringin from pomelo peel. Naringin is used as the original material, and the glycosidic bonds are cleaved one by one by chemical cracking method, further separation and purification, get high purity naringenin, this method greatly improves the yield of naringenin, but the process can be further optimized, such as more economical and effective microbial cracking, enzymatic cleavage and other preparation processes. |
pharmacodynamics | Naringenin has a variety of pharmacological activities, such as antibacterial, anti-inflammatory, antioxidant, anti-tumor, anti-cancer, anti-lung injury, etc. antibacterial and anti-inflammatory effect: inflammatory reaction refers to the body's defensive response to injured factors, which is a complex process involving a variety of cytokines. The mechanism of naringenin effectively attenuates lipopolysaccharide (LPS)-induced pulmonary inflammation is through NF-κB pathway to inhibit inflammatory cell infiltration, release of inflammatory mediators, pulmonary edema, MPO, I NOS activity, inhibition of TNF-α secretion and lung neutrophil infiltration reduces neutrophil recruitment to the lung and neutrophil-mediated oxidative damage. In addition, naringenin can also inhibit LPS /IFN-γ induced iNOS expression and nitric oxide production in glial cells, thus showing strong anti-inflammatory activity. Antioxidant effect: naringenin can prevent oxidative stress in the liver, which may be related to the activation of Nrf2 nuclear transcription factor and the attenuation of TNF-α pathway, which triggers inflammatory response in liver tissue. Proper balance between oxidants and antioxidants is a necessary condition for a long and healthy life, once the balance is broken, it may lead to dysfunction and diseases caused by oxidative stress, oxidative stress is thought to play an important role in the pathogenesis of diabetes and its complications. Anti-tumor and anti-cancer effects: the anti-tumor activity of flavonoids has attracted worldwide attention. Naringenin can inhibit the growth and proliferation of tumor cells, inhibit tumor cell metastasis and promote tumor cell apoptosis, play an anti-tumor effect. Naringenin can inhibit the activity of PI3K in MCF-7 of breast cancer cells and 3T3-L1 adipocytes, and can also play an anticancer effect by reducing the activity of Caspase-31 /CPP32 and causing HL-60 apoptosis. Anti-injury effect: naringenin can significantly inhibit the up-regulation of TNF-α,TGF-β1,MMP-9 and TIMP-1, reduce the content of malondialdehyde and hydroxyproline in lung, increase the activity of SOD,GSH-Px,HO-1, the results indicate that naringenin can effectively protect and treat ALI, which provides a new idea for clinical treatment lung injury. Hypolipidemic effect: flavonoids such as naringenin can reduce the concentration of CH and TG in the blood by inhibiting the secretion of apolipoprotein B in the liver, so as to achieve the effect of lowering blood lipids. Naringenin can also inhibit the activity of HMG- Co A reductase, reduce the blood lipid level in the model of hyperlipidemia rats, improve the abnormal lipid metabolism in hyperlipidemia rats, and inhibit the formation of atherosclerosis and fatty liver. Hypolipidemic effect: flavonoids such as naringenin can reduce the concentration of CH and TG in the blood by inhibiting the secretion of apolipoprotein B in the liver, so as to achieve the effect of lowering blood lipids. Naringenin can also inhibit the activity of HMG- Co A reductase, reduce the blood lipid level in the model of hyperlipidemia rats, improve the abnormal lipid metabolism in hyperlipidemia rats, and inhibit the formation of atherosclerosis and fatty liver. |
pharmacokinetics | naringenin can reduce the activity by P-gp, thereby inhibiting the transport of P-gp substrate; In addition, naringenin can also inhibit the expression and activity of NF-κB, thus affecting the expression of target genes and proteins, and exert anti-inflammatory, antioxidant, anti-tumor and other pharmacological effects. At home and abroad, there are scholars using Caco-2 cells and other models to study the bidirectional transport of naringenin, and to investigate the changes of naringenin absorption over time. It is found that naringenin is P-gp of the substrate, it is also shown that naringenin is subjected to P-gp efflux during absorption. |
Toxicology | because Naringenin has not been used in clinical treatment, there is little information on the toxicity of naringenin, however, preliminary studies have reported that Naringenin has less toxicity and high safety. |
references | [1] Zhu Hongping. Effects of naringenin on K562/A02 cell line P-gp and its association with NF-κB [J]. Nanchang University, 2014. [2] Ji Peng, Zhao Wenming, Yu Tong. The latest research progress of naringenin [J]. Chinese Journal of new drugs, 2015(12):1382-1386. [3] Chen Xinyun, Ma Qingping, Wang Tao, et al. Study on antitussive, expectorant and antiasthmatic effects of naringin [J]. Science and Technology of food industry, 2014, 35(19):355-358. [4] song Shuanghong, Wang de, Mo Yiyi, etc. Experimental study of naringenin in prevention and treatment of osteoporosis induced by ovariectomy in rats [J]. Chinese Journal of Pharmacy, 2015(2):154-161. [5] Yang Wenqing, Ma Jing, Yu Huarong. Study on the improvement of cognitive ability and its mechanism of naringenin in Alzheimer's disease model rats [J]. Chinese Herbal Medicine, 2013, 44(6):715-720. |
Our company specializes in processing and selling chemical raw materials, chemical products, pharmaceutical intermediates, veterinary medicine intermediates, dye intermediates, pigments, cosmetics raw materials and chemical reagents,
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FAQ:
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We deliver goods within 3 days for small order, 7-10 days for bulk order.
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8. How long is lead time
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