Apigenin

Apigenin Basic information
Description
Product Name:Apigenin
Synonyms:4,5,7-Trihydroxyflavone (apigenin);APIGENIN CRYSTALLINE;APIGENIN FROM PARSLEY;Matricaria chamomilla flower;Versuline;Pelargidenon 1449;4’,5,7-trihydroxyflavaone;4’,5,7-trihydroxy-flavon
CAS:520-36-5
MF:C15H10O5
MW:270.24
EINECS:208-292-3
Product Categories:natural product;Plant extract;pyridine series;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Protein Kinase;Signalling;Inhibitors;Tri-substituted Flavones;Biochemistry;Flavonoids;Natural Plant Extract;cosmetic;CITRIMORE;520-36-5
Mol File:520-36-5.mol
Apigenin Structure
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
pka6.53±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.
InChIInChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChIKeyKZNIFHPLKGYRTM-UHFFFAOYSA-N
SMILESC1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C=1
LogP3.020
CAS DataBase Reference520-36-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS LK9276000
10
HS Code 29329985
Hazardous Substances Data520-36-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrichEnglish
ALFAEnglish
Apigenin Usage And Synthesis
DescriptionApigenin 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. 
Chemical PropertiesPale Yellow Crystalline Solid
UsesApigenin has been shown to possess antibacterial, antiviral, antifungal, and antiparasitic activities. Although it can’t stop all types of bacteria on its own, it can be combined with other antibiotics to increase their effects.
UsesApigenin is a promising reagent for cancer therapy. Apigenin appears to have the potential to be developed either as a dietary supplement or as an adjuvant chemotherapeutic agent for cancer therapy.
UsesApigenin is an active antioxidant, anti-inflammatory, anti-amyloidogenic, neuroprotective and cognitive enhancing substance with interesting potential in the treatment/prevention of Alzheimer’s disease.
DefinitionChEBI: Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4′, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate.
Preparation4-hydroxybenzaldehyde (1.22 g, 9.97 mmol, 1.0 equiv) was added to asolution of 50% KOH (aq.) (6.72 g, 59.82 mmol, 6.0 equiv) and ethanol (3 mL) andstirred for 10 min. Then compound 9 (2.02g, 9.97 mmol, 1.0 equiv) was added to the reaction mixture and heated to 60 °C and stirred for 4 h. After cooled toroom temperature, the mixture was poured into ice water and acidified withconcentrated hydrochloric acid to pH = 3. Then the suspension was filtrated, washed and the residue was dried toafford Apigenin(2.43 g, 90%) as a red solid. 520-36-5.png
Anticancer ResearchIt 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.
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.
Purification MethodsThe current method for the purification of apigenin is crude-solvent extraction method by using solvent in small quantity and also time saving. Apigenin that was isolated from Symphyotrichum novae-angliae was obtained in large quantity and directly from extract.
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/
Apigenin Preparation Products And Raw materials
Preparation ProductsLicoflavone C–>APIGENINTRIACETATE

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