(+)-TAXIFOLIN

Base Information

• Chemical Name: (+)-TAXIFOLIN
• CAS No.: 17654-26-1
• Molecular Formula: C15H12O7
• Molecular Weight: 304.25
• Mol file: 17654-26-1.mol

Synonyms:(+)-3,3',4',5,7-PENTAHYDROXYFLAVANONE;3,3',4',5,7-PENTAHYDROXYFLAVANONE;3,5,7,3',4'-PENTAHYDROXYFLAVANONE;(+)-DIHYDROQUERCETIN;DIHYDROQUERCETIN;

Chemical Property of (+)-TAXIFOLIN

Chemical Property:

• Boiling Point: 687.6oC at 760 mmHg
• Flash Point: 264.2oC
• PSA: 127.45000
• Density: 1.702g/cm3
• LogP: 1.18630

Purity/Quality:

99% ^*data from raw suppliers

(+)-Taxifolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-Taxifolin is a flavanon compound which modulates chemopreventive genes.

Technology Process of (+)-TAXIFOLIN

There total 98 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:

C₈₄H₉₀O₂₈

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、 Usmanova,Botirov. "Glucoside of taxifolin and (+)-pinitol from Pinus sylvestris". . . Retrieved 2013.
• 2、 Ishimaru, Kanji,Omoto, Toshio,Asai, Iwao,Ezaki, Katsushi,Shimomura, Koichiro. "Taxifolin 3-arabinoside from Fragaria x ananassa". . p. 345 - 348. Retrieved 1995.
• 3、 Wungsintaweekul, Boonsong,Umehara, Kaoru,Miyase, Toshio,Noguchi, Hiroshi. "Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)". . p. 495 - 502. Retrieved 2011.
• 4、 Kasai,Hirono,Chou,Tanaka,Chen. "Sweet dihydroflavonol rhamnoside from leaves of Engelhardtia chrysolepis, a Chinese folk medicine, Hung-qi". . p. 4167 - 4170. Retrieved 1988.
• 5、 Batchu, Venkateswara Rao,Dorigundla, Aravind Reddy,Gurrapu, Raju,Macha, Lingamurthy,Vanka, Umamaheswara Sarma. "Total Synthesis of the Natural Products Ulmoside A and (2 R,3 R)-Taxifolin-6- C -β- d -glucopyranoside". . p. 1097 - 1101. Retrieved 2020/07/03.