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(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸

(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 化学構造式
30964-13-7
CAS番号.
30964-13-7
化学名:
(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸
别名:
(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸;シナリン;(1R)-1,5α-ビス[3-(3,4-ジヒドロキシフェニル)アクリロイルオキシ]-3β,4α-ジヒドロキシシクロヘキサン-1β-カルボン酸;1,3-O-ジカフェオイルキナ酸;1β,3β-ビス[3-(3,4-ジヒドロキシフェニル)プロペノイルオキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸;1,3-ジカフェオイルキナ酸;1,5-ジカフェオイルキナ酸
英語化学名:
Cynarin
英語别名:
CYNARIN;CINARAN;Cinarin;1,5-DQA;CINARINE;Aids008522;Aids-008522;Cynarin fandachem;CYNARIN(ARTICHOKE);CYNARIN(ECHINACEA)
CBNumber:
CB8261807
化学式:
C25H24O12
分子量:
516.45
MOL File:
30964-13-7.mol

(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 物理性質

融点 :
225-227°
比旋光度 :
D25 -59° (c = 2 in methanol)
沸点 :
819.9±65.0 °C(Predicted)
比重(密度) :
1?+-.0.1 g/cm3(Predicted)
貯蔵温度 :
Sealed in dry,2-8°C
溶解性:
methanol: soluble5mg/mL, clear, light yellow to yellow
外見 :
neat
酸解離定数(Pka):
2.58±0.50(Predicted)
色:
faint yellow to yellow
CAS データベース:
30964-13-7(CAS DataBase Reference)

安全性情報

Sフレーズ  24/25
WGK Germany  3
HSコード  29182900

(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 価格 もっと(2)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
関東化学株式会社(KANTO) 49062-04 シナリン
Cynarin
30964-13-7 10mg ¥55000 2021-03-23 購入
Sigma-Aldrich Japan 91801 analytical standard
Cynarin analytical standard
30964-13-7 5mg ¥67800 2021-03-23 購入

(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 化学特性,用途語,生産方法

説明

1,3-Dicaffeoylquinic acid is a polyphenol that has been found in C. scolymus. It decreases the expression and protein levels of inducible nitric oxide synthase (iNOS) when used at a concentration of 10 μM in human coronary artery smooth muscle cells (HCASMCs) treated with a cytokine mixture. 1,3-Dicaffeoylquinic acid decreases protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16F1 murine melanocytes. It inhibits melanogenesis in B16F1 cells and decreases tyrosinase activity in cell lysates when used at a concentration of 25 μM. 1,3-Dicaffeoylquinic acid (20 and 40 μM) reduces triglyceride levels in sodium oleate-induced hyperlipidemic HepG2 cells compared to hyperlipidemic control cells.

Originator

Anghirol,Biofarm

使用

Cynarin is used on MDR cells in anti-cancer therapy as an inhibitor of P-glycoprotein-mediated transport.

Manufacturing Process

18.0 g of caffeic acid, suspended in 500 ml of water, are dissolved by adding sodium bicarbonate and stirring. The solution is cooled to 2°-3°C and then, while stirring continuously, 20.0 g of phosgene dissolved in 200 ml of chloroform are added in 4 to 5 portions. After acidifying by cautiously adding iced hydrochloric acid (1:1), the solution is filtered and the collected precipitate is washed with water. Upon crystallization from glacial acetic acid, the carbonylcaffeic acid thus obtained melts at 238°-240°C (dec.).
5.0 g of carbonylcaffeic acid are suspended in 70 ml of ligroin (b. p. 120°- 140°C). After adding 6.0 g of phosphorus pentachloride and avoiding access of moisture while frequently stirring, the suspension is refluxed by boiling slowly and gently until everything is dissolved except a small amount of reddish, resinous materials that adhere to the bottom. Then solution is rapidly decanted into another flask containing 1.0 g of phosphorus pentachloride and the whole is refluxed gently for about 15-30 min, after which time evolution of hydrochloric acid ceases. This solution is left to cool on air for 1-2 h, and then, the obtained carbonylcaffeic acid chloride rapidly is filtered, washed with low-boiling ligroin and dried under vacuum at room temperature for about 1- 1.5 h. Melting point 118°-120°C.
5.0 g of carbonylcaffeic acid chloride are thoroughly mixed with 12.8 g of dry, powdered quinide in a flask immersed in an oil bath. The flask is put under vacuum and is heated to 120°C and then, slowly, to about 160°C, maintaining this temperature for about 20-30 min. The molten mass is left to cool under vacuum and then it is crushed in a mortar in the presence of water. This material is washed with water several times. The residue is dissolved in dioxin. 400 ml of cold, 3% barium hydroxide solution are added and cooled with ice water and stirring vigorously in nitrogen atmosphere. The solution is left standing insulated from contact with air for 20 h, whereupon the content is rapidly acidified and concentrated in vacuum, on a water bath, to a volume of about 80-100 ml. After cooling and standing, well protected from contact with air, the brown material is filtered off and purified by crystallization from 50% acetic acid. 1,4-Dicaffeylquinic acid is obtained, melting point 226°- 228°C.

Therapeutic Function

Choleretic, Antihyperlipidemic

(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 上流と下流の製品情報

原材料

準備製品


(1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸 生産企業

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30964-13-7((1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸)キーワード:


  • 30964-13-7
  • 1,5-DICAFFEOYLQUINIC ACID
  • 1,3-DICAFFEOYLQUINIC ACID
  • Dicaffeoylquinic Acid, 1,3-
  • Cynarin, 98%, from Lonicera japonica
  • (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
  • CYNARIN(ECHINACEA)
  • CYNARIN(ARTICHOKE)
  • CYNARIN
  • CINARINE
  • CINARAN
  • CYNARIN(ARTICHOKE)(1,5-DICAFFEOYLQUINIC ACID)(P)
  • CYNARIN(ECHINACEA)(1,3-DICAFFEOYLQUINIC ACID)(AHP)
  • (1R)-1,5α-Bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-3β,4α-dihydroxycyclohexane-1β-carboxylic acid
  • (1R)-1β,3β-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4β,5α-dihydroxycyclohexanecarboxylic acid
  • 1,3-O-Dicaffeoylquinic acid
  • 1β,3β-Bis[3-(3,4-dihydroxyphenyl)propenoyloxy]-4β,5α-dihydroxycyclohexanecarboxylic acid
  • 1,3-Di-o-caffeoylquinic acid
  • Aids008522
  • Aids-008522
  • (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)propenoyl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid
  • 1,5-Decaffeoyl quinic acid
  • 1,3-Dicaffeoylquinic Acid (Artichoke Extract)
  • Isochlorogenic acid A(3',5')
  • Cinarin
  • Cynarin Synonyms 1,3-Dicaffeoylquinic Acid
  • (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid
  • 1,5-DQA
  • 1,5-Dicaffeoylqunic acid
  • (1S,3R,4R,5R)-1,3-bis[(E)-3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enoxy]-4,5-dihydroxy-1-cyclohexanecarboxylic acid
  • Cynarin (Cynarine)
  • (1R)-1β,3β-ビス[[3-(3,4-ジヒドロキシフェニル)-1-オキソ-2-プロペニル]オキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸
  • シナリン
  • (1R)-1,5α-ビス[3-(3,4-ジヒドロキシフェニル)アクリロイルオキシ]-3β,4α-ジヒドロキシシクロヘキサン-1β-カルボン酸
  • 1,3-O-ジカフェオイルキナ酸
  • 1β,3β-ビス[3-(3,4-ジヒドロキシフェニル)プロペノイルオキシ]-4β,5α-ジヒドロキシシクロヘキサンカルボン酸
  • 1,3-ジカフェオイルキナ酸
  • 1,5-ジカフェオイルキナ酸
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