Apigenin 7-glucuronide

Base Information

• Chemical Name: Apigenin 7-glucuronide
• CAS No.: 29741-09-1
• Deprecated CAS: 68759-17-1,956511-44-7,1382137-35-0
• Molecular Formula: C₂₁H₁₈O₁₁
• Molecular Weight: 446.367
• European Community (EC) Number: 803-513-5
• UNII: 2CQ5KB3CH0
• DSSTox Substance ID: DTXSID10183893
• Nikkaji Number: J387.923B
• Wikidata: Q72443569
• Metabolomics Workbench ID: 129687
• ChEMBL ID: CHEMBL254213
• Mol file: 29741-09-1.mol

Synonyms:apigenin-7-O-beta-D-glucuronide;apigenin-7-O-glucuronide

Chemical Property of Apigenin 7-glucuronide

Chemical Property:

• Vapor Pressure: 4.28E-30mmHg at 25°C
• Melting Point: >300℃
• Boiling Point: 841.8°Cat760mmHg
• PKA: 2.73±0.70(Predicted)
• Flash Point: 299°C
• PSA: 187.12000
• Density: 1.737g/cm³
• LogP: 0.14220
• Storage Temp.: ?20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 446.08491139
• Heavy Atom Count: 32
• Complexity: 746

Purity/Quality:

95%-98% ^*data from raw suppliers

Apigenin 7-O-glucuronide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

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)C(=O)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
• Uses: Apigenin 7-Glucuronide is a metabolite of Apigenin, which 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 differentiation. Apigenin has also been reported to enhance the gap juntion intracellular communication in liver cells.

Technology Process of Apigenin 7-glucuronide

There total 13 articles about Apigenin 7-glucuronide 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: 92.0%

apigenin 7-O-β-D-glucopyranosiduronic acid methyl ester (29781-25-7,53538-13-9) → apigenin-7-O-β-D-glucuronide (29741-09-1,56317-11-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Temperature;

Reference yield:

C15H22N2O18P2 + 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) → apigenin-7-glucuronic acid (29741-09-1,56317-11-4)

Guidance literature:

With uridine 5'-diphosphate glucuronosyltransferase-1A₉; In methanol; aq. phosphate buffer; water; at 37 ℃; pH=7; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/jf304853j

Reference yield:

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) + UDP-glucuronic acid (1245697-26-0,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1) → apigenin-7-glucuronic acid (29741-09-1,56317-11-4)

Guidance literature:

With human UDP-glucuronosyltransferase 1A₉; magnesium chloride; alamethicin; D-Glucaro-1,4-lacton; at 37 ℃; pH=7.4; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1007/s11095-012-0666-z

upstream raw materials:

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

UDP-glucuronic acid

UDP-glucuronic acid

5,4'-diacetoxyflavone-7-O-D-triacetoxyglucuronic acid methyl ester

Downstream raw materials:

O¹-[5-acetoxy-2-(4-acetoxy-phenyl)-4-oxo-4H-chromen-7-yl]-O²,O³,O⁴-triacetyl-ξ-D-glucopyranuronic acid

D-glucuronic acid

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

apigenin 7-O-β-D-glucopyranosiduronic acid methyl ester

Refernces

• 1、 -. "A 5, 4' - dihydroxy flavone - 7 - O - D - glucuronic acid preparation method". . . Retrieved 2018/03/26.
• 2、 Wu, Baojian,Wang, Xiaoqiang,Zhang, Shuxing,Hu, Ming. "Accurate prediction of glucuronidation of structurally diverse phenolics by human UGT1A9 using combined experimental and in silico approaches". experimental part. p. 1544 - 1561. Retrieved 2012/07/27.