기본 정보
- CAS
522-12-3- 표준 SMILES
C[C@@H]1O[C@@H](Oc2c(-c3ccc(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
OXGUCUVFOIWWQJ-HQBVPOQASA-N- 분자식
- C21H20O11
- 평균 분자량
- 448.4 g/mol
- 단동위원소 질량
- 448.10056145
개요
Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor and a plant metabolite. It is an alpha-L-rhamnoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate.
이름 및 식별자
- 우선 이름
- Quercitrin
- IUPAC
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
- 영어명
- Quercitrin
- 분자식
- C21H20O11
- 분자량
- 448.38
이름 및 동의어
quercitrin522-12-3QuercitrosideQuercetin 3-rhamnosideQuercetrinQuercimelinThujinQuercetin-3-L-rhamnosideQuercetin 3-L-rhamnosideRhamnoside, quercetin-3Usaf cf-2QUERCETIN 3-RHAMNOPYRANOSIDE
이름 더 보기
FLAVINQUERCETIN-3-O-RHAMNOSIDEQUERCETIN-3-RHAMNOSIDEquercitrin hydrateci75720usafcf-2c.i.75720
C.I. 75720NCI-C60102Quercetin 3-O-alpha-rhamnopyranoside3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnosideCHEBI:17558DTXSID502002302Y8906LC5PQuercetin, 3-(6-deoxy-alpha-L-mannopyranoside)
데이터베이스 식별자
- CAS
522-12-3- PubChem CID
- 5280459
- DTXSID
DTXSID50200230- ChEMBL
CHEMBL2262641、CHEMBL82242- ChEBI
CHEBI:17558- UNII
- 2Y8906LC5P
- EC Number
- 208-322-5
물성
구조 계산 물성
- XLogP
- 0.9
- 극성 표면적
- 186 Ų
- 수소 결합 공여자 수
- 7
- 수소 결합 수용자 수
- 11
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 32
- 형식 전하
- 0
- 복잡도
- 741
실험 및 물리화학적 성질
Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LogP1.78
Color/FormYELLOW CRYSTALS FROM DIL METHANOL OR ETHANOL
Solubility
PRACTICALLY INSOL IN COLD WATER, ETHER; SOL IN ALCOHOL; MODERATELY SOL IN HOT WATER; SOL IN AQ ALKALINE SOLN
0.064 mg/mL at 16 °C
Melting Point
176-179 °C; FROM WATER, MP 167 °C
250 - 252 °C
Physical Description
Yellow solid; [Merck Index]
Solid
Stability/Shelf LifeIN AQ ALKALINE SOLN INTENSE YELLOW COLOR WHICH IS OXIDIZED BY AIR TO BROWN
Collision Cross Section
206.35 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
205.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.
Not Classified
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.
유해성 정보
Hazards SummaryIntraperitoneal LD50 (mouse) = 200 mg/kg; [RTECS] May cause irritation; [MSDSonline]
Hazard Classes and CategoriesNot Classified
독성 정보
Non-Human Toxicity Excerpts
QUERCITRIN WAS ASSAYED FOR MUTAGENICITY IN SALMONELLA/(RAT LIVER) MICROSOMAL ACTIVATION SYSTEM & WAS MUTAGENIC IN HISTIDINE REVERSION SYSTEM WITH FRAMESHIFT STRAIN TA98.
INFLAMMATORY DISEASE WAS SIMULATED BY INJECTION OF PLASMA KININS, KALLIDIN & BRADYKININ, WHICH INCR CAPILLARY PERMEABILITY & LYMPH FLOW (EXCEPT IN LIVER & KIDNEY). QUERCITRIN INCR LYMPH SECRETION & ANTAGONIZED KALLIDIN EFFECT @ 50-250 MG/KG.
GROWTH INHIBITION OF HELIOTHIS ZEA LARVAE BY 42 FLAVONOIDS ADDED TO DIET STUDIED. VICINAL HYDROXYLATION NECESSARY FOR ACTIVITY, BUT WAS NOT SUFFICIENT FOR ALL COMPD SINCE SOME WERE INACTIVE. SOME COMPD WITH DIFFERENT POLARITIES EQUALLY ACTIVE (QUERCITRIN & QUERCETIN).
QUERCITRIN WAS NOT MUTAGENIC IN SALMONELLA/MAMMALIAN MICROSOME TEST.
안전 데이터
- wgk
- 3
- rtecs
- UZ5950000
- HS 번호
- 29389090
- safety_code
- 24/25
- F 고인화성물질
- 10-23
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Metabolism/Metabolites
YIELDS QUERCETIN IN ASPERGILLUS; WESTLAKE DWS, CAN J MICROBIOL 9: 211 (1963); YIELDS QUERCITRIN QUINONE PROBABLY IN POLYPORUS; PICKARD MA & WESTLAKE DWS, CAN J BIOCHEM 48: 1351 (1970). /FROM TABLE/
Quercitrin has known human metabolites that include L-Rhamnose, Quercetin, and alpha-L-Rhamnose.
Cellular LocationsCytoplasm
용도 및 제조
Uses
From the tree Aesculus hippocastanum L., Hippocastanaceae; Has been used to dye textiles; Main constituent of flavine yellow shade; [Merck Index] Formerly used as a dye for wool; [HSDB]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
DYE FORMERLY USED ON WOOL MORDANTED WITH TIN AND ALUM
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of Manufacturing
EXTRACTION (AS MIXTURE WITH QUERCETIN) FROM BARK OF QUECUS TINCTORIA WITH HIGH PRESSURE STEAM
FROM AESCULUS HIPPOCASTANUM L, HIPPOCASTANACEAE: HORHAMMER ET AL, ARCH PHARM 292, 113 (1959).
General Manufacturing InformationHAS BEEN USED AS TEXTILE DYE. FLAVINE YELLOW SHADE IS PREPARED BY EXTRACTING QUERCITRON BARK WITH HIGH PRESSURE STEAM AND CONSISTS MAINLY OF QUERCITRIN; TISDALE, CAN TEXTILE J 57, 44 (1941).
응용 분야
관련 반응
0건
현재 필터 조건에 해당하는 반응 기록이 없습니다.
화합물 노트
불러오는 중…