ルチン三水和物

Rutin

HCID 5280805

基本情報

CAS
153-18-4
標準SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)c(O)c4)oc4cc(O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey
IKGXIBQEEMLURG-NVPNHPEKSA-N
分子式
C27H30O16
平均分子量
610.5 g/mol
単同位体質量
610.15338488

概要

Rutin is a rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. It has a role as an antioxidant and a metabolite. It is a rutinoside, a tetrahydroxyflavone, a disaccharide derivative and a quercetin O-glucoside.

名称と識別子

優先名称
Rutin
IUPAC
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
現地名
ルチン三水和物
英語名
Rutin
分子式
C27H30O16
分子量
610.52

名称と別名

RUTIN153-18-4rutosideQuercetin 3-rutinosideBirutanPhytomelinSophorinIlixanthinMyrticolorinGlobulariacitrinOsyritrinPaliuroside
名称をさらに表示
ルチン三水和物ルトシド3',4',5,7-テトラヒドロキシ-3-[6-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシルオキシ]フラボンC.I.ナチュラルイエロー102-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-3-[[6-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシル]オキシ]-4H-1-ベンゾピラン-4-オンクエルセチン3-ルチノシド3-[6-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシルオキシ]-3',4',5,7-テトラヒドロキシフラボン3-[(6-O-α-L-ラムノピラノシル-β-D-グルコピラノシル)オキシ]-3',4',5,7-テトラヒドロキシフラボン3-[6-O-α-L-ラムノピラノシル-β-D-グルコピラノシルオキシ]-3',4',5,7-テトラヒドロキシフラボン5,7-ジヒドロキシ-2-(3,4-ジヒドロキシフェニル)-3-[(6-O-α-L-ラムノピラノシル-β-D-グルコピラノシル)オキシ]-4H-1-ベンゾピラン-4-オン3-[[6-O-(α-L-ラムノピラノシル)-β-D-グルコピラノシル]オキシ]-3',4',5,7-テトラヒドロキシフラボンクエルセチン3-ラムノグルコシド2-(3,4-ジヒドロキシフェニル)-3-[(6-O-(α-L-ラムノピラノシル)-β-D-グルコピラノシル)オキシ]-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン3-[6-O-(α-L-ラムノピラノシル)-β-D-グルコピラノシルオキシ]-3',4',5,7-テトラヒドロキシフラボンルチンクエルセチン3-O-β-ルチノシドクエルセチン3-O-ルチノシド2-(3,4-ジヒドロキシフェニル)-3-[6-O-(α-L-ラムノピラノシル)-β-D-グルコピラノシルオキシ]-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン3-[[6-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシル]オキシ]-5,7-ジヒドロキシ-2-(3,4-ジヒドロキシフェニル)-4H-1-ベンゾピラン-4-オン3',4',5,7-テトラヒドロキシ-3-(6-O-α-L-ラムノピラノシル-β-D-グルコピラノシルオキシ)フラボンRutinumRoutinebioflavonoidilixathinRutin Standard
Tanrutin3-Rutinosyl quercetinQuercetin-3-rutinosideQuercetin 3-O-rutinosideYunxiangganRutosidoRutine3-Rhamnoglucosylquercetin

データベース識別子

CAS
153-18-4、207671-50-9
PubChem CID
5280805
DTXSID
DTXSID3022326
ChEMBL
CHEMBL226335
ChEBI
CHEBI:28527
UNII
5G06TVY3R7
EC Number
205-814-1、683-619-4
Nikkaji
J818D

物性

構造計算による物性

XLogP
-1.3
極性表面積
266 Ų
水素結合供与体数
10
水素結合受容体数
16
回転可能結合数
6
重原子数
43

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
CosmeticsHair conditioning; Skin conditioning; Antioxidant
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility · 2 件

0.125 mg/mL

Poorly soluble in water whereas readily soluble in pyridine.

Melting Point125 °C

物理化学的性質

融点
195 °C · 195 °C (dec.)(lit.)
比旋光度
23 · D23 +13.82° (ethanol); D23 -39.43° (pyridine)
沸点
576.13 °C · 576.13°C (rough estimate)
比重(密度)
1.3881 · 1.3881 (rough estimate)
屈折率
1.765 · 1.7650 (estimate)
貯蔵温度
2 · Keep in dark place,Sealed in dry,2-8°C

化学的性質

化学的特性Pale-Yellow Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 143 reports by companies from 1 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 58.9% (63 of 107) of all reports.

Warning

危険有害性情報

Regulatory Information · 3 件

Chemical: 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

Status: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26165

4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and Categories · 2 件

Skin Irrit. 2 (38.3%)

Acute Tox. 4 (100%)

毒性情報

Toxicity SummaryA 2021 review notes that Rutin can be considered safe for clinical use, and that no toxic signs were observed in acute and chronic toxicity studies of rats, guinea pigs and rabbits.

安全データ

F
8
wgk
3
tsca
TSCA listed
rtecs
VM2975000
毒性
LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)
hs_code
29381000

化学と産業

薬理情報

ATC Code · 3 件

C05CA01

C - Cardiovascular system

QC - Cardiovascular system

Mechanism of Action · 1 件

A 2022 review of Rutin focused on its protective effects on the heart, liver, and kidneys against various chemical and natural toxins. The antioxidant effects involve enhancement of various antioxidant enzymes, Nrf2/HO-1 pathway activation, Glutathione (GSH) elevation, and malondialdehyde (MDA) reduction. The anti-inflammatory effects involve inhibition of IL-1β, IL-6, TGF-β1, COX-2, iNOS, TLR4, and XO. The antiapoptotic effects involve inhibition of free radicals, caspase-3/-7/-9, hsp70, HMGB1, and p53, and elevation of antiapoptotic protein Bcl-2.

Absorption, Distribution and Excretion · 1 件

A 2021 review notes that poor water solubility of Rutin is a major drawback, and that efforts have been made to improve its solubility by introducing a new functional group, e.g., a carboxylate group on its sugar moiety. Also, drug delivery systems have been developed to improve Rutin's pharmacokinetic properties and therapeutic potential, e.g., using liposomes, polymeric micelles and nanoparticles as carriers for rutin.

Cellular LocationsCytoplasm

用途と製造

UsesUse (kg; approx.) in Germany (2009): >25000
Household ProductsInformation on 1 consumer products that contain Rutin in the following categories is provided:
Use ClassificationCosmetics -> Hair conditioning; Skin conditioning; Antioxidant
General Manufacturing Information4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-: ACTIVE
応用分野 · 4 件

解説ルチン毛細血管の抵抗力を高め、透過性の亢進(こうしん)を抑制する作用を示す代表的化合物である。毛細血管が弱くてもろいためにおこる出血性の病気の治療や予防に血管補強剤や止血剤として用いられ、また高血圧や脳出血、心悸(しんき)亢進や狭心症などにも用いられることがある。アメリカのFDA(食品医薬品局Food and Drug Administration)では無効とされているが、日本では血管壁に存在するヒアルロン酸を溶かしてその透過性を高めるヒアルロニダーゼの反応を阻止するとして、臨床的に用いられることがある。小学館 日本大百科全書(ニッポニカ)

説明Rutin is widely found in nature and is almost contained in all of the Rutaceae and Sectaceae plants, especially abundant in Rutaceae, Rutaceae, Epacridaceae of leguminous, buckwheat of Polygonaceae, Eulali of Hypericum, Berchemia polyphylla var. leioclada of Tetranychidae, and wild wutong leaves of thistle, which are also used as raw materials in rutin extraction. In addition, it also exists in the Ilex pubescens of Aquifoliaceae, Forsythia of Oleaceae, pagoda tree pod of Leguminosae, tobacco, jujube, apricots, flavedo, tomatoes, and other plants.At present, rutin in China mainly extracted from the Sophora japonica Linn of leguminous, which is listed in top grade of Shen Nong’s Classic Materia Medica. In addition, tartary buckwheat, which is rich in rutin and flavonoids, is native to India and now produced in China’s northwest, southwest, north, south, and other places.

来歴In the mid-1930s, Hungarian scientist Szent Gyorgy firstly separated the flavonoid mixture. After the German pharmacy firstly made it into ranosine in 1942, the concept of vitamin P has been established worldwide. Further study proved that rutin was the most important flavonoids of vitamin P. These compounds were certified to have effects on many diseases in medical.Recently, the research of rutin mainly focuses on the extraction process improvement, pharmacological effects, and pharmacodynamics research, aiming at improvement of its bioavailability through the development of different dosage forms. As for the extraction process, new extraction and purification methods have been developed since the original alkali extraction acid precipitation method. These methods greatly improve its extraction efficiency and reduce cost, including hot water precipitation, hot water extraction with macroporous resin adsorbing purification, ultrasonic radiation, hot water extraction with alcohol precipitation, cold alkali percolation extraction with acid precipitation, continuous reflux extraction, ethanol extraction, supercritical CO2 extraction, and enzymatic hydrolysis .In recent years, advanced rutin dosage forms, such as rutin cyclodextrin saturation, HPMC controlled release tablets, solid dispersion tablets, coprecipitate, and rutin effervescent particles, greatly improve the rutin dissolution rate and its bioavailability.

使用Found in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.

調製方法 · 1 件

純化方法The vitamin crystallises from MeOH or water/EtOH, dry it in air, then dry it further for several hours at 110o or in high vacuum at 120o. It forms yellow crystals from EtOH/Me2CO/H2O (2:1:1). It has also been purified by passing (0.5g) through a Kieselgel column (30 x 5cm) with EtOAc/MeOH/H2O (100:20:15), and after 750mL have passed through, the yellow fraction of 250mL gives the glycoside (0.3g) on evaporation. [H.rhammer et al. Chem Ber 101 1183 1968, Marini-Bettòlo Gazz Chim Ital 80 631 1950, Beilstein 18/5 V 519.]

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INTATRADE GmbH+49 3493/605464 · [email protected]

補足説明

定義本品は、次の化学式で表されるフラボノイドである。

定義ChEBI: A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.

関連反応

9 件

化合物ノート

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