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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 1,020
実験および物理化学的性質
Solubility
0.125 mg/mL
Poorly soluble in water whereas readily soluble in pyridine.
Physical Description
Solid
Yellowish powder
Collision Cross Section
251.61 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
232.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
245.04 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
234.7 Ų [M-H]-
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
- 溶解性
- 50 mg/mL · ピリジン: 50 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 6.17 · 6.17±0.40(Predicted)
- 色
- 黄色から緑色
- 臭い (Odor)
- 無臭
- 水溶解度
- 12.5 g/100mL · 12.5g/100mL
- Merck
- 8304 · 8304
- 安定性
- 吸湿性
- 主な用途
- 医薬品
- 化粧品成分の機能
- 抗酸化物質ヘアコンディショニングスキンコンディショニング
- LogP
- -2.02 · -2.020 (est)
- CAS データベース
- 153 · 153-18-4(CAS DataBase Reference)
- NISTの化学物質情報
- -3 · Flavone-3-rutinoside, 3,3',4',5,7-pentahydroxy(153-18-4)
- EPAの化学物質情報
- Rutin (153-18-4)
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
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
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
Hazard Classes and Categories
Skin Irrit. 2 (38.3%)
Acute Tox. 4 (100%)
毒性情報
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
- risk_code
- 22-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 24/25-36-26
化学と産業
薬理情報
ATC Code
C05CA01
C - Cardiovascular system
QC - Cardiovascular system
Mechanism of Action
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
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.
用途と製造
応用分野
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
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.]
上流・下流製品情報
下流製品
サプライヤー100 社
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
化合物ノート
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