基本情報
- 標準SMILES
O=c1cc(-c2ccccc2)oc2c(O)c(O)ccc12- InChIKey
COCYGNDCWFKTMF-UHFFFAOYSA-N- 分子式
- C15H10O4
- 平均分子量
- 254.24 g/mol
- 単同位体質量
- 254.0579088
概要
7,8-dihydroxyflavone is a dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's. It has a role as a tropomyosin-related kinase B receptor agonist, an antioxidant, an antidepressant, an antineoplastic agent and a plant metabolite.
名称と識別子
- 優先名称
- 7,8-Dihydroxyflavone
- IUPAC
- 7,8-dihydroxy-2-phenylchromen-4-one
- 現地名
- 7,8-ジヒドロキシフラボン
- 英語名
- 7,8-Dihydroxyflavone
- 分子式
- C15H10O4
- 分子量
- 254.24
名称と別名
名称をさらに表示
データベース識別子
- CAS
38183-03-8- PubChem CID
- 1880
- DTXSID
DTXSID00191568- ChEMBL
CHEMBL75267- ChEBI
CHEBI:140464- UNII
- ADB6MA8ZV2
- EC Number
- 253-812-4
- Nikkaji
- J294.607F
物性
構造計算による物性
- XLogP
- 3.3
- 極性表面積
- 66.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 1
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 384
実験および物理化学的性質
Solubility
Very slightly soluble
Very slightly soluble (in ethanol)
Collision Cross Section
173.79 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 243 · 243-246°C
- 沸点
- 494.4 · 494.4±45.0 °C(Predicted)
- 比重(密度)
- 1.443 · 1.443±0.06 g/cm3(Predicted)
- FEMA
- 4830 · 4830 | 7,8-DIHYDROXYFLAVONE
- 貯蔵温度
- Inert atmosphere,Room Temperature
- 溶解性
- 24 mg/mL · DMSO:可溶24mg/mL
- 外見
- 個体
- 酸解離定数(Pka)
- 6.86 · 6.86±0.40(Predicted)
- 色
- 黄色または黄褐色
- JECFA Number
- 2259 · 2259
- 安定性
- -20 °Cで最大1週間保存できます。 · 防湿。 DMSOまたはエタノール溶液で-20°Cで最大1週間保存できます。
- InChI
- InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
- InChIKey
- COCYGNDCWFKTMF-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=CC=C2)OC2=C(O)C(O)=CC=C2C(=O)C=1
- LogP
- 2.76 · 2.760 (est)
- CAS データベース
- 38183 · 38183-03-8(CAS DataBase Reference)
化学的性質
化学的特性White crystalline powder or Yellow Solid, soluble in methanol, ethanol, DMSO and other organic solvents, from the dried root of Pulsatilla chinensis (Bge.) Regel.
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 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
安全データ
- wgk
- 3
- rtecs
- DJ3004000
- hs_code
- 2932990090
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
用途と製造
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
応用分野
説明7,8-Dihydroxyflavone(7,8-DHF) is a naturally occurring flavone found in the tree Godmania aesculifolia. It is a selective tyrosine kinase receptor B(TrkB) agonist that has neurotrophic effects in various neurological diseases such as stroke and Parkinson's disease. 7,8-Dihydroxyflavone binds to the TrkB receptors in a similar way to BDNF, or brain derived neurotrophic factor. When the TrkB receptor is activated, neuroprotective and neurogenetive effects occur in neurons, which tend to affect the dendrites. Dendrites are what reach out from the neurons into the synapse to participate in signaling with other neurons. 7,8-DHF has been shown to promote the growth of these dendrites, and to help restore communication between neurons in animal models.
使用7,8-Dihydroxyflavone is disubstituted flavone that acts as a small-molecule TrkB agonist. 7,8-Dihydroxyflavone has been shown to reverse memory deficits and BACE1 elevation in a mouse model of Alzheimer''s disease. 7,8-Dihydroxyflavone may also provide a therapeutic option in the treatment of other neorological disorders such as Rett syndrome and PTSD. It has recently been shown to counteract the inhibition of NMDA receptor caused by lead poisoning and confer protective effects in live rats.
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