Apigenin

Base Information

• Chemical Name: Apigenin
• CAS No.: 520-36-5
• Deprecated CAS: 461015-54-3
• Molecular Formula: C15H10O5
• Molecular Weight: 270.241
• Hs Code.: 29329985
• European Community (EC) Number: 208-292-3
• UNII: 7V515PI7F6
• ChEMBL ID: CHEMBL28
• DSSTox Substance ID: DTXSID6022391
• Metabolomics Workbench ID: 23090
• NCI Thesaurus Code: C68466
• Nikkaji Number: J6.601J
• NSC Number: 83244
• Pharos Ligand ID: 8RC47GHQ6Y29
• RXCUI: 1368130
• Wikidata: Q424567
• Wikipedia: Apigenin
• Mol file: 520-36-5.mol

Synonyms:Apigenin

Chemical Property of Apigenin

Chemical Property:

• Appearance/Colour: Pale Yellow Crystalline Solid
• Vapor Pressure: 6E-13mmHg at 25°C
• Melting Point: 345-350 °C
• Refractive Index: 1.732
• Boiling Point: 555.5 °C at 760 mmHg
• PKA: 6.53±0.40(Predicted)
• Flash Point: 217 °C
• PSA: 90.90000
• Density: 1.548 g/cm³
• LogP: 2.57680
• Storage Temp.: −20°C
• Solubility.: DMSO: 27 mg/mL
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 411

Purity/Quality:

99%, ^*data from raw suppliers

Apigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
• Recent ClinicalTrials: Low Level Diode Laser Versus Topical Chamomile in Management of Chemotherapy Induced Oral Mucositis
• Recent NIPH Clinical Trials: A study of the chamomile on sleep quality.
• Description: 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.
• Uses: Apigenin is an active antioxidant, anti-inflammatory, anti-amyloidogenic, neuroprotective and cognitive enhancing substance with interesting potential in the treatment/prevention of Alzheimer's disease. Apigenin 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. Apigenin 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.

Technology Process of Apigenin

There total 117 articles about Apigenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5)

Guidance literature:

With sulfuric acid; iodine; In dimethyl sulfoxide; at 100 ℃; for 1.5h;

DOI:10.1211/jpp.59.12.0012

Reference yield: 92.0%

2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one (110865-03-7) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5)

Guidance literature:

2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one; 4-hydroxy-benzaldehyde; With sodium hydroxide; In ethanol; water;

With hydrogenchloride; Further stages.;

DOI:10.1016/j.tetlet.2004.08.180

Reference yield: 90.0%

4',5,7-trimethoxyflavone (5631-70-9) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5)

Guidance literature:

With pyridine hydrochloride; at 180 - 190 ℃; for 6h; Inert atmosphere;

DOI:10.3184/174751912X13285269293913

upstream raw materials:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

6-bromo-5-hydroxy-7,4'-dimethoxyflavone

dihydrokaempferol

4'-O-methylapigenin 6-C-β-D-glucopyranoside

Downstream raw materials:

apigenin 7-O-glucoside

5,7-dihydroxy-2-(4-hydroxyphenyl-3,5-D₂)-4H-1-benzopyran-4-one-3,6,8-D₃

5-hydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Refernces

• 1、 Ibrahim, Abdel-Rahim Sayed. "Biotransformation of chrysin and apigenin by Cunninghamella elegans". . p. 671 - 673. Retrieved 2005.
• 2、 Komilov,Agzamova,Isaev,Eshbakova. "New Flavonoid Glycoside from Thalictrum minus". . . Retrieved 2020.
• 3、 Bae, KiHwan,Jin, WenYi,Thuong, Phuong Thien,Min, Byung Sun,Na, MinKyun,Lee, Young Mi,Kang, Sam Sik. "A new flavonoid glycoside from the leaf of Cephalotaxus koreana". . p. 409 - 413. Retrieved 2007.
• 4、 Martens, Stefan,Forkmann, Gert,Matern, Ulrich,Lukacin, Richard. "Cloning of parsley flavone synthase I". . p. 43 - 46. Retrieved 2001.
• 5、 Zykova,Pivenko. "-". . . Retrieved 1975.
• 6、 -. "COSMETIC COMPOSITION FOR SKIN IMPROVEMENT COMPRISING GREEN BARLEY EXTRACT". . . Retrieved 2022/02/05.
• 7、 Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao. "Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer". . p. 12089 - 12108. Retrieved 2021/09/06.