Apigenin 7-O-glucoside

Base Information

• Chemical Name: Apigenin 7-O-glucoside
• CAS No.: 578-74-5
• Molecular Formula: C21H20O10
• Molecular Weight: 432.384
• Hs Code.: 29389090
• NSC Number: 407303
• Wikidata: Q104170422
• Mol file: 578-74-5.mol

Synonyms:NSC407303;Apigenin 7-O-glucoside;Apigenin-7-O-glucoside;Apigenin 7-beta-D-glucoside;Anthemoside;Apigenin 7-O-.beta.-D-glucoside;7-O-(.beta.-D-Glucosyl)apigenin;Apigenin 7-O-.beta.-D-glucopyranoside;APIGENIN, 7-B-D-GLYCOPYRANOSIDE;apigenin7-glucoside;Oprea1_225308;Flavone base + 3O, O-Hex;SCHEMBL12014216;4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-;KMOUJOKENFFTPU-UHFFFAOYSA-N;STL451018;Apigenin, 7-.beta.-D-glucopyranoside;NCI60_003873;FT-0622446;4',5,7-Trihydroxyflavone 7-.beta.-D-glucoside;5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl hexopyranoside

Chemical Property of Apigenin 7-O-glucoside

Chemical Property:

• Vapor Pressure: 3.14E-26mmHg at 25°C
• Melting Point: 230-237 °C
• Refractive Index: 1.717
• Boiling Point: 788.9 °C at 760 mmHg
• PKA: 6.13±0.40(Predicted)
• Flash Point: 280.7 °C
• PSA: 170.05000
• Density: 1.642 g/cm³
• LogP: 0.04990
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 432.10564683
• Heavy Atom Count: 31
• Complexity: 675

Purity/Quality:

98%,99%, ^*data from raw suppliers

Apigetrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 34/35

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• Uses: Apigenin 7-Glucoside is a by-product during the synthesis of Isorhoifolin (I819700), a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects.

Technology Process of Apigenin 7-O-glucoside

There total 25 articles about Apigenin 7-O-glucoside 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: 93.0%

7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin (119249-30-8) → apigenin 7-O-glucoside (578-74-5)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 13h;

DOI:10.1016/j.tet.2004.01.001

Reference yield: 77.0%

5,4'-di-O-hexanoylapigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (1145669-48-2) → apigenin 7-O-glucoside (578-74-5)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2018.11.015

Reference yield: 8.0%

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) → apigenin 7-O-glucoside (578-74-5)

Guidance literature:

In dimethyl sulfoxide; for 168h; regioselective reaction; Microbiological reaction;

DOI:10.1016/j.bioorg.2019.01.046

upstream raw materials:

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

crotonoylcosmosiin

anisofolin-A

Downstream raw materials:

apiin

D-glucose

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

D-Glucose

Refernces

• 1、 Tschan, Gabriela M.,Koenig, Gabriele M.,Wright, Anthony D.,Sticher, Otto. "Chamaemeloside, a new flavonoid glycoside from Chamaemelum Nobile". . p. 643 - 646. Retrieved 1996.
• 2、 Sordon, Sandra,Pop?oński, Jaros?aw,Tronina, Tomasz,Huszcza, Ewa. "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca". . . Retrieved 2019/02/13.
• 3、 Peng, Meng,Shahzad, Raheel,Gul, Ambreen,Subthain, Hizar,Shen, Shuangqian,Lei, Long,Zheng, Zhigang,Zhou, Junjie,Lu, Dandan,Wang, Shouchuang,Nishawy, Elsayed,Liu, Xianqing,Tohge, Takayuki,Fernie, Alisdair R.,Luo, Jie. "Differentially evolved glucosyltransferases determine natural variation of rice flavone accumulation and UV-tolerance". . . Retrieved 2017/12/26.