Basic information Chemical Properties Occurance Preparation Health Benifits Description References Safety Related Supplier
Apigenin Chemical Properties
- Melting point:>300 °C(lit.)
- Boiling point:333.35°C (rough estimate)
- Density 1.2319 (rough estimate)
- refractive index 1.6000 (estimate)
- storage temp. −20°C
- solubility DMSO: 27 mg/mL
- form powder
- color yellow
- Merck 14,730
- BRN 262620
- CAS DataBase Reference520-36-5(CAS DataBase Reference)
Apigenin Usage And Synthesis
- Chemical PropertiesApigenin (C15H10O5, CAS registry No. 520-36-5) is also called 4’,5,7-trihydroxyflavone, which is a pale yellow crystalline solid. Its melting point is 345-350 oC, and flash point is 217 oC. The solubility of apigenin is 27 g/L in DMSO. Apigenin has a very low solubility in water (1.35 μg/mL) and high permeability. Taking into consideration its high permeability, apigenin is categorized as a Class II drug according to Biopharmaceutics Classification System (BCS), whose characteristics are low solubility and high permeability. Pure apigenin is generally regarded as unstable for long term storage at room temperature, and thus it requires storage at -20°C..
- OccuranceApigenin is one of the most widespread flavonoids in plants and formally belongs to the flavone sub-class. Of all the flavonoids, apigenin is one of the most widely distributed in the plant kingdom, and one of the most studied phenolics. Apigenin is present principally as glycosylated in significant amount in vegetables (parsley, celery, onions) fruits (oranges), herbs (chamomile, thyme, oregano, basil), and plant-based beverages (tea, beer, and wine). Plants belonging to the Asteraceae, such as those belonging to Artemisia, Achillea, Matricaria, and Tanacetum genera, are the main sources of this compound. However, species belonging to other families, such as the Lamiaceae, for instance, Sideritis and Teucrium, or species from the Fabaceae, such as Genista, showed the presence of apigenin in the aglycone form and/or its C- and O-glucosides, glucuronides, O-methyl ethers, and acetylated derivatives.
- PreparationBiogenetically, apigenin is a product of the phenylpropanoid pathway and may be obtained from both phenylalanine and tyrosine, two shikimate-derived precursors. From phenylalanine, cinnamic acid is formed by non-oxidative deamination and then by oxidation at C-4, which is then converted to p-coumaric acid, whereas from tyrosine p-coumaric acid is formed directly by deamination. After activation with CoA, p-coumarate is condensed with three malonyl-CoA residues and then subjected to aromatization by chalcone synthase to form chalcone, which is further isomerized by chalcone isomerase to form naringenin; finally, a flavanone synthase oxidizes naringenin to apigenin.
- Health BenifitsA high number of studies carried out over the years have indicated that apigenin has many interesting pharmacological activities and nutraceutical potential. As an example, its properties as an antioxidant are well known, and it can also be a therapeutic agent to overcome diseases like inflammation, autoimmune, neurodegenerative disease, and even several types of cancers. It has a low intrinsic toxicity on normal versus cancerous cells, compared with other structurally related flavonoids.
- DescriptionApigenin (chemically known as 4′, 5, 7-trihydroxyflavone, with molecular formula C15H10O5) is with molecular weight of 270.24. It is a naturally occurring plant flavone and is abundantly present in common fruits such as grapefruit, plant-derived beverages, and vegetables such as parsley, onions, oranges, tea, chamomile, wheat sprouts and in some seasonings.
Apigenin has gained particular interest in recent years as a beneficial and health promoting agent owing to its low intrinsic toxicity and its striking effects on normal versus cancer cells, compared with other structurally-related flavonoids. It has been increasingly recognized as a cancer and tumor chemopreventive agent (for breast cancer, cervical cancer, colon cancer, hematologic cancer, lung cancer, ovaria cancer, prostate cancer, skin cancer, thyroid cancer, endometrial cancer, gastric cancer, liver cancer, adrenal cortical cancer, leukemia, and neuroblastoma) owing to its anti-inflammatory, antioxidant and anticancer properties.
- References Sanjeev Shukla, Sanjay Gupta (2010) Apigenin: a promising molecule for cancer prevention, 27, 962-978.
- Chemical PropertiesPale Yellow Crystalline Solid
- OccurrenceChamomile is a perennial found in Europe.
- Usesantispasmodic, antineoplastic, topoisomerase I inhibitor
- UsesInduces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 uM) by inhibiting MAP kinase activity. Also inhibits the proliferation of malignant tum or cells by G2/M arrest and induces morphological differentiation. Apigenin has also been reported to enhance the gap juntion intracellular communication in liver cells.
- UsesHas been used to dye Cr mordanted wool yellow. The color is fast to soap.
- General DescriptionThe herb known as chamomile is derived from the plants Matricaria chamomilla (German, Hungarian, or genuine chamomile) and Anthemis nobilis (English, Roman, or common chamomile). Plants from the two genera have similar activities. The medicinal components are obtained from the flowering tops. The flowers are dried and used for chamomile teas and extracts. Chamomile has been used medicinally for at least 2,000 years. The Romans used the herb for its medicinal properties, which they knew were antispasmodic and sedative.
The herb also has a long history in the treatment of digestive and rheumatic disorders. The activity of chamomile is found in a light blue essential oil that composes only 0.5% of the flower. The blue color is caused by chamazulene, 7-ethyl-1,4-dimethylazulene . This compound is actually a byproduct of processing the herb. The major component of the oil is the sesquiterpene (-)-α-bisabolol. Also present are apigenin, angelic acid, tiglic acid, the terpene precursors (farnesol, nerolidol, and germacranolide) coumarin, scopoletin-7-glucoside, umbelliferone, and herniarin. Much of the effect of chamomile is caused by bisabolol . Bisabolol is a highly active anti-inflammatory agent in various rodent inflammation and arthritis tests.
- Biological ActivityProtein kinase inhibitor. Suppresses tumor-promoting effects of TPA and exhibits antiproliferative activity in human breast cancer cells (IC 50 values are 59.44 and 31.15 μ M at 24 and 72 hrs respectively). Activates both the intrinsic and extrinsic apoptotic pathways and displays anti-inflammatory, hypotensive, antispasmodic and antioxidant properties in vivo .
- Anticancer ResearchIt is a flavone compound found in many fruits and vegetables and abundant in chamomiletea, parsley, celeriac, and celery. It induces apoptosis by targeting leptin/leptin receptor pathway and by targeting caspase-dependent extrinsic pathway aswell as STAT3 signaling pathway in lung adenocarcinoma and BT-474 breast cancercells, respectively (Singh et al. 2016b). It shows antitumor activity against breastcancer MCF-7 cells and colon cancer HCT 116 cells and is a mediator of cancerchemoprevention and an inducer of autophagy. It can be used to treat colon canceras it induces apoptosis in colon cancer cells. It also increase melanogenesis in B16cells by activating the p38 MAPK pathway (Wang et al. 2012).
- Purification MethodsCrystallise it from aqueous pyridine or aqueous EtOH. It dyes wool yellow when mixed with Cr ions. [Beilstein 18 H 181, 18 I 396, 18 II 178, 18 III/IV 2682, 18/4 V 574.]
- D-(-)-Salicin Icariin Quercetin dihydrate Apigenin 7-O-β-D-glucuronide,Glucuronyl-7-apigenin ISOFLAVONES THEAFLAVIN Riboflavin Diosmin APIGENIN-7-NEOHESPERIDOSIDE hplc,apigenin 7-O-hesperidoside 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE ARTEMISININ 3,7,3',4'-TETRAMETHYLGOSSYPETIN Myricitrin CHRYSOERIOL 3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE EUPATORIN-5-METHYL ETHER Myricetin 3,4'-DIMETHOXY-3',5,7-TRIHYDROXYFLAVONE
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- Feb 26，2020