Supplier Related Products Identification Chemical Properties Questions And Answer Safety Data Hazard Information Spectrum Detail Well-known Reagent Company Product Information
WebSite >  CAS DataBase List  > 520-36-5

520-36-5

Supplier Related Products Identification Chemical Properties Questions And Answer Safety Data Hazard Information Spectrum Detail Well-known Reagent Company Product Information

Product Image

Identification

Name
Apigenin
CAS
520-36-5
Synonyms
4',5,7-TRIHYDROXYFLAVONE
4,5,7-TRIHYDROXYFLAVONE
4',5,7-TRIHYROXYFLAVONE
5,7,4'-TRIHYDROXYFLAVONE
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
7,4',5-TRIHYDROXYFLAVONE
APIGENIN
CHAMOMILE
2-(p-hydroxyphenyl)-5,7-dihydroxychromone
4’,5,7-trihydroxyflavaone
4’,5,7-trihydroxy-flavon
5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-on
apigenine
apigenol
c.i.naturalyellow1
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
4,5,7-Trihydroxyflavone (apigenin)
APIGENIN CRYSTALLINE
APIGENIN FROM PARSLEY
Matricaria chamomilla flower
EINECS(EC#)
208-292-3
Molecular Formula
C15H10O5
MDL Number
MFCD00006831
Molecular Weight
270.24
MOL File
520-36-5.mol

Chemical Properties

Appearance
Pale Yellow Crystalline Solid
Melting point 
>300 °C (lit.)
mp 
>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

pka
6.53±0.40(Predicted)
color 
yellow

Usage
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 tumor cells by G2/M arrest and induces morphological
Merck 
14,730
BRN 
262620
InChIKey
KZNIFHPLKGYRTM-UHFFFAOYSA-N
CAS DataBase Reference
520-36-5(CAS DataBase Reference)

Questions And Answer

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] https://en.wikipedia.org/wiki/Apigenin
[3] http://bodynutrition.org/apigenin/

Safety Data

Hazard Codes 
Xi
Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
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

RTECS 
LK9276000


10
HS Code 
29329900
Hazardous Substances Data
520-36-5(Hazardous Substances Data)

Hazard Information

Occurrence
Chamomile is a perennial found in Europe.
Uses
antispasmodic, antineoplastic, topoisomerase I inhibitor
Uses
Has been used to dye Cr mordanted wool yellow. The color is fast to soap.
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.
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.]

Spectrum Detail

Well-known Reagent Company Product Information

SupplierMore