Aromadendrin

Base Information

• Chemical Name: Aromadendrin
• CAS No.: 480-20-6
• Deprecated CAS: 20257-56-1,29400-53-1,4050-91-3,5150-32-3,56297-98-4
• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.257
• European Community (EC) Number: 687-473-2
• UNII: 7YA4640575
• DSSTox Substance ID: DTXSID8075411
• Nikkaji Number: J12.461C
• Wikipedia: Aromadendrin
• Wikidata: Q956217
• RXCUI: 1601985
• Metabolomics Workbench ID: 50064
• ChEMBL ID: CHEMBL9323
• Mol file: 480-20-6.mol

Synonyms:aromadedrin;aromadendrin;dihydro-kaempferol;dihydro-kempferol;dihydrokaempferol;dihydrokempferol

Chemical Property of Aromadendrin

Chemical Property:

• Vapor Pressure: 3.32E-17mmHg at 25°C
• Melting Point: 237～241℃
• Refractive Index: 1.728
• Boiling Point: 639 °C at 760 mmHg
• PKA: 7.42±0.60(Predicted)
• Flash Point: 247.3 °C
• PSA: 107.22000
• Density: 1.599 g/cm³
• LogP: 1.48070
• Storage Temp.: ?20°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 288.06338810
• Heavy Atom Count: 21
• Complexity: 392

Purity/Quality:

98%, ^*data from raw suppliers

Aromadendrin ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,Xn
• Hazard Codes: N,Xn
• Statements: 50-22
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• Uses: Aromadendrin is a flavonoid extract that displays antioxidant and cytotoxic effects. Also, potential anti-cholinesterase activity and β-site amyloid precursor protein cleaving enzyme 1 inhibitory compounds.

Technology Process of Aromadendrin

There total 16 articles about Aromadendrin 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: 89.0%

(2R*,3S*)-tetrakis(O-methoxymethyl)isosalipurpol epoxide → (+/-)-aromadendrin (480-20-6,22425-48-5,104486-98-8,118333-31-6,56297-98-4)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 0.25h;

Reference yield:

naringenin (480-41-1) → kaempferol (520-18-3) + Aromadendrin (480-20-6,22425-48-5,104486-98-8,118333-31-6,56297-98-4)

Guidance literature:

With FLAVONOL SYNTHASE; FLAVANONE 3-HYDROXYLASE; TrxA-His-AtF₃H; TrxA-His-AtFLS₁; In aq. buffer; at 40 ℃; for 0.666667h; pH=7.2; Temperature; pH-value; Time; Enzymatic reaction;

DOI:10.1021/acs.jafc.8b01299

Reference yield:

dihydrokaempferol (724434-08-6,56297-98-4) → (2S,3S)-3,40,5,7-tetrahydroxyflavanone (118333-31-6,56297-98-4) + Aromadendrin (480-20-6,22425-48-5,104486-98-8,118333-31-6,56297-98-4)

Guidance literature:

With DAICEL CHIRALPAK IA; In ethanol; hexane; Resolution of racemate;

DOI:10.1016/j.bmc.2015.09.042

upstream raw materials:

tetrakis(methoxymethoxy)isosalipurpol Epoxide

tetrakis(methoxymethoxy) isosalipurpol

2,4,6-trihydroxyacetophenone

4-hydroxy-benzaldehyde

Downstream raw materials:

7-O-Methyldihydrokaempferol, 7-O-methylaromadendrin

(2R,3R)-2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone

3,4',7-triacetoxyaromadendrin

dihydrokaempferol tetra-acetate

Refernces

• 1、 Jiang, Wen-Jun,Ishiuchi, Kan'Ichiro,Furukawa, Megumi,Takamiya, Tomoko,Kitanaka, Susumu,Iijima, Hiroshi. "Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship". . p. 6922 - 6929. Retrieved 2015/11/11.
• 2、 Takahashi, Hiroshi,Kubota, Yumiko,Igushi, Mieko,Fang, Lin,Onda, Masayuki. "HETEROCYCLES. XVIII. SYNTHESIS OF THE RACEMATES OF NATURALLY OCCURRING FLAVONOIDS". . p. 369 - 377. Retrieved 2007/10/02.