基本情報
- CAS
480-40-0- 標準SMILES
O=c1cc(-c2ccccc2)oc2cc(O)cc(O)c12- InChIKey
RTIXKCRFFJGDFG-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
Chrysin is a dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent, an anti-inflammatory agent, a plant metabolite and an EC 2.7.11.18 (myosin-light-chain kinase) inhibitor. It is a dihydroxyflavone and a 7-hydroxyflavonol.
名称と識別子
- 優先名称
- Chrysin
- IUPAC
- 5,7-dihydroxy-2-phenylchromen-4-one
- 現地名
- クリシン
- 英語名
- Chrysin
- 分子式
- C15H10O4
- 分子量
- 254.24
名称と別名
chrysin480-40-05,7-DihydroxyflavoneChrysine5,7-dihydroxy-2-phenylchromen-4-one4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-phenyl-5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-oneFLAVONE, 5,7-DIHYDROXY-DTXSID1022396NSC-4074363CN01F5ZJ5DTXCID902396
名称をさらに表示
クリシン5,7-ジヒドロキシ-2-フェニル-4H-1-ベンゾピラン-4-オン5,7-ジヒドロキシフラボン2-(フェニル)-5-ヒドロキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン2-フェニル-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オンクリシデノン14385,7-ジヒドロキシ-2-フェニル-4H-クロメン-4-オン5,7-DIHYDROXY-2-PHENYL-CHROMEN-4-ONEhrysinNSC 407436Chrysin-RMCHRYSIN(RG)
CHEBI:750955,7-dihydroxy-flavoneRefChem:5686207-549-75,7-Dihydroxy-2-phenyl-4H-chromen-4-oneCrysinChrysinic acidMFCD00006834
データベース識別子
- CAS
480-40-0
物性
構造計算による物性
- XLogP
- 2.1
- 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
Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
LogP
3.520
3.52
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point285.50 °C. @ 760.00 mm Hg
Physical DescriptionLight yellow solid; [Merck Index] Yellow powder; [Alfa Aesar MSDS]
Collision Cross Section
157.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1022396]
151.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167.64 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 284 · 284-286 °C(lit.)
- 沸点
- 357.45 °C · 357.45°C (rough estimate)
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 80% (8 of 10) of all reports.
Warning
H315 (20%): 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 10 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (20%)
毒性情報
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- F
- 10
- wgk
- 3
- rtecs
- LK8329050
- hs_code
- 29329990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- hazard_class
- IRRITANT
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/MetabolitesChrysin has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.
Cellular LocationsMembrane
用途と製造
UsesFrom heartwood of Pinus monticola; [Merck Index]
応用分野
解説クリシン,淡黄色のりょう柱状晶．融点275 ℃．熱アルコール類，氷酢酸，アニリンに易溶，水にほとんど不溶，冷アルコール類，クロロホルム，エーテルに難溶．アルコール溶液は塩化鉄(Ⅲ)により褐紫色を呈する．λmax 270，329 nm(log ε 4.40，3.90)．森北出版「化学辞典（第2版）
説明Chrysin is a natural flavonoid with antioxidant, anti-inflammatory, and anticancer properties. It blocks COX-2 gene expression, PGE2 production, and hydroxyl radical formation in LPS-induced RAW 264.7 cells. Chrysin inhibits insulin-induced HIF-1α expression (~50% at 10 μM) in human prostate cancer DU145 cells and blocks DU145 xenograft-induced angiogenesis in vivo. In a mouse model of ischemia/reperfusion injury, chrysin decreased pro-inflammatory gene expression and oxidative stress, resulting in a reduction of infarct volume and neurological defects.
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