기본 정보
- 표준 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- 분자식
- C27H30O16
- 평균 분자량
- 610.5 g/mol
- 단동위원소 질량
- 610.15338488
개요
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.
이름 및 식별자
- 우선 이름
- 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
이름 및 동의어
RUTIN153-18-4rutosideQuercetin 3-rutinosideBirutanPhytomelinSophorinIlixanthinMyrticolorinGlobulariacitrinOsyritrinPaliuroside
이름 더 보기
Tanrutin3-Rutinosyl quercetinQuercetin-3-rutinosideQuercetin 3-O-rutinosideYunxiangganRutosidoRutine3-Rhamnoglucosylquercetin
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- -1.3
- 극성 표면적
- 266 Ų
- 수소 결합 공여자 수
- 10
- 수소 결합 수용자 수
- 16
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 43
- 형식 전하
- 0
- 복잡도
- 1,020
실험 및 물리화학적 성질
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
0.125 mg/mL
Poorly soluble in water whereas readily soluble in pyridine.
Melting Point125 °C
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]-
안전 및 규제
GHS 분류
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
유해성 정보
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
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and Categories
Skin Irrit. 2 (38.3%)
Acute Tox. 4 (100%)
독성 정보
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.
화학 및 산업
약리 정보
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.
Cellular LocationsCytoplasm
용도 및 제조
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
관련 반응
9건
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