Taxifolin

Base Information

• Chemical Name: Taxifolin
• CAS No.: 480-18-2
• Deprecated CAS: 17654-26-1,20254-28-8,24198-96-7,28929-10-4,5117-01-1,5323-70-6,98006-93-0,20254-28-8,24198-96-7,28929-10-4,5117-01-1,5323-70-6
• Molecular Formula: C15H12O7
• Molecular Weight: 304.256
• Hs Code.: 29329990
• European Community (EC) Number: 207-543-4
• UNII: 9SOB9E3987,EAS93SC1VS
• DSSTox Substance ID: DTXSID8022450,DTXSID301017215
• Nikkaji Number: J90.394I
• Wikipedia: Taxifolin
• Wikidata: Q412191
• Pharos Ligand ID: 5HHNGZ6H2QBZ
• Metabolomics Workbench ID: 51100
• ChEMBL ID: CHEMBL66
• Mol file: 480-18-2.mol

Synonyms:dihydroquercetin;taxifolin

Chemical Property of Taxifolin

Chemical Property:

• Appearance/Colour: Yellowish powder
• Vapor Pressure: 7.51E-20mmHg at 25°C
• Melting Point: 230-233 °C (dec.)
• Refractive Index: 1.762
• Boiling Point: 687.6 °C at 760 mmHg
• PKA: 7.39±0.60(Predicted)
• Flash Point: 264.1 °C
• PSA: 127.45000
• Density: 1.702 g/cm³
• LogP: 1.18630
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 304.05830272
• Heavy Atom Count: 22
• Complexity: 428

Purity/Quality:

95%-98% ^*data from raw suppliers

(+)-transTaxifolin ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• Recent ClinicalTrials: Taxifolin/Ergothioneine and Immune Biomarkers in Healthy Volunteers (TaxEr)
• Description: Taxifolin, a chemical substance extracted from pine plants such as larch and Douglas fir. It belongs to the bioflavonoid pseudo-vitamin P, and its scientific name is dihydroquercetin. Japanese scholar Fukui first isolated it from the leaves of conifers (Chamaecyparis obtusa), and its biological activity was subsequently discovered and confirmed.
• Uses: Reference Standard in the analysis of herbal medicinal products

Technology Process of Taxifolin

There total 81 articles about Taxifolin 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%

(αS*,βR*)-α,β-epoxy-3,4,2',4',6'-pentakis(methoxymethoxy)chalcone → (+/-)-taxifolin (480-18-2,24198-97-8,98006-93-0,111003-33-9,114761-89-6,17654-26-1,5117-01-1)

Guidance literature:

With hydrogenchloride; methanol; for 0.5h; Ambient temperature;

Reference yield: 73.0%

3,4,2',4',6'-pentamethoxymethoxychalcone epoxide → (+/-)-taxifolin (480-18-2,24198-97-8,98006-93-0,111003-33-9,114761-89-6,17654-26-1,5117-01-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; water; at 55 ℃; for 2h;

DOI:10.1021/jm900735p

Reference yield:

(2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1) → cyanidin (13306-05-3) + quercetol (117-39-5,74893-81-5) + 2R,4R-flavan-3,3,4-triol + (-)-epitaxifolin (480-18-2,24198-97-8,98006-93-0,111003-33-9,114761-89-6,17654-26-1,5117-01-1) + taxifolin (480-18-2,17654-26-1,5117-01-1)

Guidance literature:

With anthocyanidin synthase from Vitis vinifera; water; In aq. acetate buffer; at 35 ℃; for 0.5h; pH=6.3; Mechanism; Enzymatic reaction;

DOI:10.1021/acs.jafc.8b06968

upstream raw materials:

astilbin

(-)-chalcone epoxide

(+)-taxifolin 3-O-β-D-xylopyranoside

(2R,3R)-(+)-dihydroquercetin-3-β-D-glucopyranoside

Downstream raw materials:

(2S,3S)-taxifolin 3-O-β-D-glucoside

catechin-(4α->8)-ent-epicatechin

Peracetylated catechin-(4α-8)-catechin-(4α-8)-catechin procyanidin trimer

[4,8]-2,3-trans-3,4-trans:2,3-trans-deca-O-acetyl-bi-(+)-catechin

Refernces

• 1、 Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao. "Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli". . . Retrieved 2021/05/31.
• 2、 Zhang, Jia-Rong,Trossat-Magnin, Claudine,Bathany, Katell,Delrot, Serge,Chaudière, Jean. "Oxidative Transformation of Leucocyanidin by Anthocyanidin Synthase from Vitis vinifera Leads only to Quercetin". . p. 3595 - 3604. Retrieved 2019/03/29.