520-36-5 Usage
Description
Apigenin is a widely distributed flavonoid belonging to the flavone sub-class, found in various plants, vegetables, fruits, herbs, and plant-based beverages. It is a pale yellow crystalline solid and is one of the most studied phenolic compounds due to its numerous health-promoting properties.
Uses
Used in Alzheimer's Treatment/Prevention:
Apigenin is used as an active antioxidant, anti-inflammatory, anti-amyloidogenic, neuroprotective, and cognitive enhancing substance for the treatment and prevention of Alzheimer's disease.
Used in Antimicrobial Applications:
Apigenin is used as an antibacterial, antiviral, antifungal, and antiparasitic agent. It can be combined with other antibiotics to enhance their effects and increase their efficacy against various types of bacteria.
Used in Cancer Therapy:
Apigenin is used as a promising reagent for cancer therapy. It has the potential to be developed as a dietary supplement or as an adjuvant chemotherapeutic agent, contributing to the fight against cancer.
Used in the Food Industry:
Apigenin is used as a natural compound in the food industry, where it is found in significant amounts in vegetables (parsley, celery, onions), fruits (oranges), herbs (chamomile, thyme, oregano, basil), and plant-based beverages (tea, beer, and wine). It adds to the nutritional value and health benefits of these products.
Used in Pharmaceutical Applications:
Apigenin is used in the pharmaceutical industry for its potential therapeutic applications, including the development of new drugs and supplements for various health conditions, such as Alzheimer's disease and cancer.
Preparation
4-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.
Anticancer Research
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. 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 Methods
The 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.
Check Digit Verification of cas no
The CAS Registry Mumber 520-36-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 0 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 520-36:
(5*5)+(4*2)+(3*0)+(2*3)+(1*6)=45
45 % 10 = 5
So 520-36-5 is a valid CAS Registry Number.
InChI:InChI=1/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
520-36-5Relevant articles and documents
Regioselective ortho-Hydroxylations of Flavonoids by Yeast
Sordon, Sandra,Madej, Anna,Pop?oński, Jaros?aw,Bartmańska, Agnieszka,Tronina, Tomasz,Brzezowska, Ewa,Juszczyk, Piotr,Huszcza, Ewa
, p. 5525 - 5530 (2016)
Natural flavonoids, such as naringenin, hesperetin, chrysin, apigenin, luteolin, quercetin, epicatechin, and biochanin A, were subjected to microbiological transformations by Rhodotorula glutinis. Yeast was able to regioselectively C-8 hydroxylate hesperetin, luteolin, and chrysin. Naringenin was transformed to 8- and 6-hydroxyderivatives. Quercetin, epicatechin, and biochanin A did not undergo biotransformation. A metabolic pathway for the degradation of chrysin has been elucidated. The metabolism of chrysin proceeds via an initial C-8 hydroxylation to norwogonin, followed by A-ring cleavage to 4-hydroxy-6-phenyl-2H-pyran-2-one.
Secondary metabolites of an Algerian Phlomis bovei and their antioxidant activities
Zaabat,Akkal,Darboure,Laouer,Franca, M. G. Dijoux,Duddeck, Helmut
, p. 454 - 455 (2010)
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Gusev et al.
, (1977)
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FLAVONOID GLYCOSIDES OF ARTEMISIA MONOSPERMA AND A. HERBA-ALBA
Saleh, Nabiel A. M.,El-Negoumy, Sabry I.,Abd-Alla, Mohamed F.,Abou-Zaid, Mamdouh M.,Dellamonica, G.,Chopin, J.
, p. 201 - 203 (1985)
Ten flavonoid glycosides were isolated and identified from Artemisia monosperma: vicenin-2, lucenin-2, acacetin 7-glucoside, acacetin 7-rutinoside, the 3-glucosides and 3-rutinosides of quercetin and patuletin, and the 5-glucosides of quercetin and isorhamnetin.From Artemisia herba-alba eight flavonoid glycosides were isolated and identified: isovitexin, vicenin-2, schaftoside, isoschaftoside and the 3-glucosides and 3-rutinosides of quercetin and patuletin.Key Word Index - Artemisia monosperma; A herba-alba; Compositae; flavone and flavonol glycosides.
A NEW GLYCOSYLATED FLAVONOID, 7-O-α-L-RHAMNOPYRANOSYL-4'-O-RUTINOSYLAPIGENIN, IN THE EXUDATE FROM GERMINATING SEEDS OF Sesbania rostrata
Messems, Eric,Montagu, Marc Van,Bruyn, Andre De,Jans, Arnold W. H.
, p. 241 - 254 (1989)
The title apigenin triglycoside was isolated (4 mg/6000 seeds) by reversephase column chromatography as the major u.v.-absorbing compound in the exudate of germinating seeds of Sesbania rostrata.The structure was assigned on the basis of u.v. spectra, f.a.b.-mass-spectral and 2D-n.m.r. data.The triglycoside was released continuously from the germinating seeds, but at a decreasing rate during the first two weeks.
Apigenin Glycosides from Astragalus galegiformis
Kavtaradze,Alaniya,Pichette,Mshvildadze
, p. 156 - 157 (2021/01/29)
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8-azacyclo-substituted chromone derivative as well as preparation method and pharmaceutical application thereof
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Paragraph 0051-0053, (2021/10/27)
The invention discloses an 8-azacyclo-substituted chromone derivative as well as a preparation method and pharmaceutical application thereof, and belongs to the field of medicinal chemistry. The invention provides the 8-azacyclo-substituted chromone compound with selective PARP1/2 inhibitory activity, and the 8-azacyclo-substituted chromone compound can be used for preparing medicines for preventing or treating PARP1/2 defective tumors and has wide market application and development prospects.