2-hydroxy-1,4-dihydronaphthalene-1,4-dione

• ChemBase编号: 75303
• 分子式: C10H6O3
• 平均质量: 174.15284
• 单一同位素质量: 174.03169405
• SMILES: O=C1c2ccccc2C(=O)C=C1O
• Canonical SMILES: O=C1C=C(O)C(=O)c2c1cccc2
• InChI: InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
• InChIKey: CSFWPUWCSPOLJW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
• IUPAC传统名: 2-hydroxy-4H-naphthalene-1,4-dione; HANA; 2-hydroxy-1,4-dihydronaphthalene-1,4-dione; mehendi
• 别名: 2-羟基-1,4-萘醌; 2-Hydroxy-1,4-naphthoquinone; 2-hydroxynaphthalene-1,4-dione; Henna; Lawsone; Lawsone; Natural Orange 6; Hennotannic acid; C.I. 75480; Lawsone; 2-Hydroxy-1,4-naphthoquinone

登记号

• CAS号: 83-72-7
• EC号: 201-496-3
• MDL号: MFCD00001678
• Beilstein号: 1565260
• 默克索引号: 145393
• PubChem SID: 162040221; 24895653
• PubChem CID: 6755
• CHEMBL: 240963
• 美国药典/FDA物质标识码: TLH4A6LV1W
• 维基百科标题: Lawsone
• Color Index Number: 75480

理论计算性质

• Acid pKa: 5.519285
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.6842885
• LogD (pH = 7.4): -0.9010882
• Log P: 0.97566026
• 摩尔折射率: 48.1506 cm^3
• 极化性: 17.46068 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: almost insoluble in water
• 外观: Yellow prisms
• 熔点: 192-195 °C (dec.)(lit.); 195-196 °C (decomposition); ca 193°C dec.
• 紫外吸收波长: λmax 452 nm

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: QL8200000
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 22-36-68; 36/37/38; R36 R37 R38
• 安全公开号: 26-36/37; 26-37/39; S26 S36 S37 S39
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• 半数致死量: 100 mg/kg
• GHS危险声明: H315-H319-H335; H341-H302-H319
• GHS警示性声明: P261-P305 + P351 + P338; P280-P281-P305+P351+P338-P301+P312-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 生物活性机理: Inhibitor of NADPH-cytochrome C reductase

产品相关信息

• 纯度: 97%; 98%; 98+%
• 级别: technical grade
• 杂质: 20% lawsone-3,3′-dimer
• 生物来源: Isol. from Lawsonia spp., henna and seeds of Lomatia ferruginea. Also from Impatiens spp.
• 应用领域: Antineoplastic; Antispasmodic agent, fungicide, bactericide and ingredient of sunscreen preparations; Possesses antiinflammatory, analgesic and antipyretic activity
• Empirical Formula (Hill Notation): C10H6O3

详细说明

Sigma Aldrich - 184098

Application
Lawsone (2-hydroxy-1,4-naphthoquinone) is the active ingredient of henna (Lawsonia alba), the crushed leaves of which are used as a cosmetic dye.

Sigma Aldrich - H46805

包装
10, 25, 100 g in glass bottle

参考文献

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 86A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 79D, (ir)
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• Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, 484
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• Chapelle, J.P., Phytochemistry, 1974, 13, 662, (isol, deriv)
• Mehendale, A.R. et al., Phytochemistry, 1975, 14, 801, (isol)
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