基本情報
- CAS
522-12-3- 標準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- 分子式
- C21H20O11
- 平均分子量
- 448.4 g/mol
- 単同位体質量
- 448.10056145
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- クェルシトリン
- 英語名
- Quercitrin
- 分子式
- C21H20O11
- 分子量
- 448.38
名称と別名
quercitrin522-12-3QuercitrosideQuercetin 3-rhamnosideQuercetrinQuercimelinThujinQuercetin-3-L-rhamnosideQuercetin 3-L-rhamnosideRhamnoside, quercetin-3Usaf cf-2QUERCETIN 3-RHAMNOPYRANOSIDE
名称をさらに表示
クエルシトリンクエルシトロシドクエルシメリンクエルセチン3-α-L-ラムノピラノシド2-(3,4-ジヒドロキシフェニル)-3-(α-L-ラムノピラノシルオキシ)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン5,7-ジヒドロキシ-2-(3,4-ジヒドロキシフェニル)-3-(6-デオキシ-α-L-マンノピラノシルオキシ)-4H-1-ベンゾピラン-4-オン3-(α-L-ラムノピラノシルオキシ)-3',4',5,7-テトラヒドロキシフラボンクエルセチン3-O-α-L-ラムノピラノシドクエルセチン3-ラムノピラノシドクエルセチン3-ラムノシドツジン3-[(6-デオキシ-α-L-マンノピラノシル)オキシ]-2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン3',4',5,7-テトラヒドロキシ-3-(α-L-ラムノピラノシルオキシ)フラボン2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-3-[(6-デオキシ-α-L-マンノピラノシル)オキシ]-4H-1-ベンゾピラン-4-オン5,7-ジヒドロキシ-2-(3,4-ジヒドロキシフェニル)-3-(α-L-ラムノピラノシルオキシ)-4H-1-ベンゾピラン-4-オン3-(α-L-ラムノピラノシルオキシ)-2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オン3-(α-L-ラムノピラノシルオキシ)-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2-(3,4-ジヒドロキシフェニル)-5,7-ジヒドロキシ-3-(6-デオキシ-α-L-マンノピラノシルオキシ)-4H-1-ベンゾピラン-4-オンクエルセチン-3-L-ラムノシドクエルセチン-3-O-ラムノシド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)
データベース識別子
- CAS
522-12-3- PubChem CID
- 5280459
- DTXSID
DTXSID50200230- ChEMBL
CHEMBL2262641、CHEMBL82242- ChEBI
CHEBI:17558- UNII
- 2Y8906LC5P
- EC Number
- 208-322-5
- Nikkaji
- J1.578D
物性
構造計算による物性
- XLogP
- 0.9
- 極性表面積
- 186 Ų
- 水素結合供与体数
- 7
- 水素結合受容体数
- 11
- 回転可能結合数
- 3
- 重原子数
- 32
- 形式電荷
- 0
- 複雑度
- 741
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 174 · 174-183°C
- 沸点
- 477.14 °C · 477.14°C (rough estimate)
- 比重(密度)
- 1.3943 · 1.3943 (rough estimate)
- 屈折率
- 1.5376 · 1.5376 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO（わずかに）、メタノール（わずかに、超音波処理）
- 外見
- 個体
- 酸解離定数(Pka)
- 6.17 · 6.17±0.40(Predicted)
- 色
- 薄黄色～濃黄色
- Merck
- 8125 · 8125
- BRN
- 68135 · 68135
- 安定性
- 吸湿性
- 主な用途
- 食品および飲料
- InChIKey
- OXGUCUVFOIWWQJ-HQBVPOQASA-N
- SMILES
- C[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O
- LogP
- 0.579 · 0.579 (est)
- CAS データベース
- 522 · 522-12-3(CAS DataBase Reference)
化学的性質
化学的特性Quercitrin is a yellow crystalline powder that can dissolve in ethanol and alkaline solutions. It is hardly soluble in cold water and ether. It is derived from the bark of Acacia, the leaves of lateral cypress and leucistic monkey earrings, as well as the flowers of grass cotton (Gossypiumherbaceum L.) of the mallow family. Quercitrin is also a constituent of th e dye quercitron.It is present in Tartary buckwheat and certain oak species like white oak or European red oak.
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazards SummaryIntraperitoneal LD50 (mouse) = 200 mg/kg; [RTECS] May cause irritation; [MSDSonline]
Hazard Classes and CategoriesNot Classified
毒性情報
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.
安全データ
- F
- 10-23
- wgk
- 3
- rtecs
- UZ5950000
- hs_code
- 29389090
- safety_code
- 24/25
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 522-12-3(Hazardous Substances Data)
化学と産業
薬理情報
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
用途と製造
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).
応用分野
解説イソアロキサジンの複素環を母核とする化学構造をもつ黄色物質の一般名．生体内で酸化還元反応，酸素添加反応の補酵素成分となる．リボフラビン，FAD，FMNのほか，リボフラビンの光分解産物であるルミクロム，ルミフラビンなどがある．
一般的な説明Quercitrin[522-12-3], also known as Quercetin 3-rhamnoside, is a flavonoid compound found in plants and is the primary active ingredient in Acacia. It possesses multiple beneficial effects such as antioxidant, antitumour, hypoglycaemic, and hypolipidemic properties. The 2010 edition of Chinese Pharmacopoeia selects quercetin as the control product for the identification and content determination of Acacia, which is used to control the quality of Acacia.
上流・下流製品情報
下流製品
サプライヤー100 社
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Syntechem Co.,Ltd[email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18049756717 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
補足説明
定義ChEBI: 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 antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a monosaccharide derivative, a tetrahydroxyflavone, an alpha-L-rhamnoside and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate.
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…