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| 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. |
2-8°C |
| solubility |
DMSO: 27 mg/mL |
| form |
powder |
| pka |
6.53±0.40(Predicted) |
| color |
yellow |
| Merck |
14,730 |
| BRN |
262620 |
| Stability: |
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| InChIKey |
KZNIFHPLKGYRTM-UHFFFAOYSA-N |
| CAS DataBase Reference |
520-36-5(CAS DataBase Reference) |
| Provider |
Language |
| SigmaAldrich |
English |
| ALFA |
English |
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| Apigenin Usage And Synthesis |
| Chemical Properties |
Apigenin (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.. |
| Occurance |
Apigenin 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. |
| Preparation |
Biogenetically, 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 Benifits |
A 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. |
| Description |
Apigenin (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 |
[1] Sanjeev Shukla, Sanjay Gupta (2010) Apigenin: a promising molecule for cancer prevention, 27, 962-978.
[2] #
[3] # |
| Description |
Apigenin (520-36-5) is a plant flavonoid with antioxidant properties. It has been reported to have myriad effects on biochemical pathways including kinase inhibition (CK2, PKC, ERK)1-3, CYP2CP inhibition4, inhibition of cellular proliferation via G2/M cell cycle arrest3,5, reduction of HIF-1 and VEGF expression6, and inhibition of nitric oxide and PGE2 synthesis7. |
| Chemical Properties |
Pale Yellow Crystalline Solid |
| Occurrence |
Chamomile is a perennial found in Europe. |
| Uses |
antispasmodic, antineoplastic, topoisomerase I inhibitor |
| Uses |
Induces 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. |
| Uses |
Has been used to dye Cr mordanted wool yellow. The color is fast to soap. |
| General Description |
The 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 Activity |
Protein 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 . |
| Biochem/physiol Actions |
A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53. Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
| Anticancer Research |
It 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 Methods |
Crystallise 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.] |
| References |
1) Lin et al. (1997) Suppression of protein kinase C and nuclear oncogene expression as possible molecular mechanisms of cancer chemoprevention by apigenin and curcumin; J. Cell. Biochem. Suppl. 28-29 39 2) Zhao et al. (2011) Apigenin inhibits proliferation and induces apoptosis in human multiple myeloma cells through targeting the trinity of CK2, Cdc37 and Hsp90; Mol. Cancer, 10 10 3) Yin et al. (2001) Apigenin inhibits growth and induces G2/M arrest by modulating cyclinCDK regulators and ERK MAP kinase activation in breast carcinoma cells; Anticancer Research 21 413 4) Si et al. (2009) Mechanism of CYP2C9 inhibition by flavones and flavonols; Drug Metabolism and Disposition, 37 629 5) Sato et al. (1994) Apigenin induces morphological differentiation and G2-M arrest in rat neuronal cells; Biochem. Biophys. Res. Commun. 204 578 6) Fang et al. (2007) Apigenin inhibits tumor angiogenesis through decreasing HIF-1alpha and VEGF expression; Carcinogenesis, 28 858 7) Raso et al. (2001) Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1; Life Sci., 68 921 |
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| Apigenin Preparation Products And Raw materials |
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China (Mainland)
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