基本情報
- CAS
60-82-2- 標準SMILES
O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O- InChIKey
VGEREEWJJVICBM-UHFFFAOYSA-N- 分子式
- C15H14O5
- 平均分子量
- 274.27 g/mol
- 単同位体質量
- 274.08412354
概要
Phloretin is a member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. It has a role as an antineoplastic agent and a plant metabolite. It is functionally related to a dihydrochalcone.
名称と識別子
- 優先名称
- Phloretin
- IUPAC
- 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
- 現地名
- β-(4-ヒドロキシフェニル)-2',4',6'-トリヒドロキシプロピオフェノン
- 英語名
- Phloretin
- 分子式
- C15H14O5
- 分子量
- 274.27
名称と別名
phloretin60-82-2Dihydronaringenin3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-onePhloretol1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-DTXSID6022393S5J5OE47MKFEMA NO. 4390NSC-4072922',4,4',6'-TetrahydroxydihydrochalconeDTXCID702393
名称をさらに表示
2',4,4',6'-テトラヒドロキシ-α,β-ジヒドロ-trans-カルコン1-(2,4,6-トリヒドロキシフェニル)-3-(4-ヒドロキシフェニル)-1-プロパノンフロレチンβ-(4-ヒドロキシフェニル)-2',4',6'-トリヒドロキシプロピオフェノンフロレトールジヒドロナリンゲニン3-(4-ヒドロキシフェニル)-1-(2,4,6-トリヒドロキシフェニル)-1-プロパノン2',4',6'-トリヒドロキシ-3-(4-ヒドロキシフェニル)プロピオフェノンフロレチン, 結晶フロレチン, 98%β-(4-ヒドロキシフェニル)-2′,4′,6′-トリヒドロキシプロピオフェノン3-(4-ヒドロキシフェニル)-1-(2,4,6-トリヒドロキシフェニル)プロパン-1-オン2′,4,4′,6′-テトラヒドロキシ-α,β-ジヒドロ-trans-カルコン3-(4-ヒドロキシフェニル)-1-[2,4,6-トリヒドロキシフェニル]プロパン-1-オンFloretinoretinRJC 02792Phloridin
物性
構造計算による物性
- XLogP
- 2.6
- 極性表面積
- 98 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 5
- 回転可能結合数
- 4
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 312
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.123 mg/mL at 16 °C
Slightly soluble in water
Sparingly soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point263.5 °C
Physical Description
Solid
Pearl white powder; Sweet aroma
Collision Cross Section
159.02 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
160.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
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 72.4% (118 of 163) of all reports.
Warning
H315 (27.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 163 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and CategoriesSkin Irrit. 2 (27.6%)
安全データ
- F
- 3-10
- wgk
- 3
- hs_code
- 29145090
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 37/39-26-36
- hazard_class
- IRRITANT
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/MetabolitesPhloretin has known human metabolites that include Phloretin, 4p-hydroxy-glucuronide and Phloretin, 2p-hydroxy-glucuronide.
Tissue LocationsFibroblasts
Cellular LocationsMembrane
用途と製造
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
応用分野
用途PKCの動態研究や調節機構の解明のツール。
使用As glucose transport inhibitor, Phloretin can inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.
使用Phloretin has been used:to study its effect on the 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-d-glucose (2-NBDG) and 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-l-glucose (2-NBDLG) uptaketo incubate microvesicles in order to inhibit GLUT1 (glucose transporter 1)-mediated transport in radioactive ligand up-take assayas a component of KRH buffer to stop glucose uptake by trophoblast cells in vitro
一般的な説明Phloretin is a dihydrochalcone flavonoid with antioxidant activity usually found in apples and apple-derived products. It is extensively used for peroxynitrite scavenging and the inhibition of lipid peroxidation. It has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells.
調製方法
純化方法Crystallise phloretin from aqueous EtOH. [Zemplen & Bognár Chem Ber 75 1040 1942, Zemplén Chem Ber 76 386 1943, Beilstein 8 IV 3518.]
関連反応
5 件
化合物ノート
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