142905
拉帕醇
98%
别名:
2-羟基-3-(3-甲基-2-丁烯基)-1,4-萘醌, 黄钟花醌
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关于此项目
经验公式（希尔记法）:
C15H14O3
化学文摘社编号:
分子量:
242.27
PubChem Substance ID:
UNSPSC Code:
12352100
Colour Index Number:
75490
NACRES:
NA.22
EC Number:
201-563-7
MDL number:
Assay:
98%
Form:
solid
InChI key
CIEYTVIYYGTCCI-UHFFFAOYSA-N
InChI
1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3
SMILES string
C\C(C)=C\CC1=C(O)C(=O)c2ccccc2C1=O
assay
98%
form
solid
mp
141-143 °C (lit.)
solubility
ethanol: soluble 10 mg/mL, clear, light yellow to yellow
functional group
ketone
Quality Level
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General description
拉帕醇是一种天然萘醌化合物，来源于紫葳科（黄钟木属）。
Application
拉帕醇用于合成拉帕醇金属配合物 。
Biochem/physiol Actions
拉帕醇对许多病原体具有抗菌属性 。具有抗炎、镇痛及抗菌属性 。它是黑腹果蝇杂合子 上皮性肿瘤的抑制剂。
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Kenneth O Eyong et al.
Bioorganic & medicinal chemistry letters, 18(20), 5387-5390 (2008-10-03)
Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is
Ingrid L Cockburn et al.
Biological chemistry, 392(5), 431-438 (2011-03-24)
Plasmodium falciparum heat shock protein 70 (PfHsp70-1) is thought to play an essential role in parasite survival and virulence in the human host, making it a potential antimalarial drug target. A malate dehydrogenase based aggregation suppression assay was adapted for
Inactivation of β-Lapachone Cytotoxicity by Filamentous Fungi that Mimic the Human Blood Metabolism.
Camila Raquel Paludo et al.
European journal of drug metabolism and pharmacokinetics, 42(2), 213-220 (2016-04-10)
β-Lapachone is a drug candidate in phase II clinical trials for treatment of solid tumors. The therapeutic efficacy of β-lapachone is closely related to its metabolism, since this o-naphthoquinone produces cytotoxic effect after intracellular bioreduction by reactive oxygen species formation.
Xueyin Zu et al.
Phytotherapy research : PTR, 33(9), 2337-2346 (2019-06-22)
Lapachol is a 1,4-naphthoquinone that is isolated from the Bignoniaceae family. It has been reported to exert anti-inflammatory, antibacterial, and anticancer activities. However, the anticancer activity of lapachol and its molecular mechanisms against esophageal squamous cell carcinoma (ESCC) cells have
Gabrieli L Parrilha et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 25(1), 55-62 (2011-08-09)
Complex [Bi(Lp)(2)]Cl was obtained with 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione, "lapachol" (HLp). Lapachol, [Bi(Lp)(2)]Cl and BiCl(3) were evaluated in a murine model of inflammatory angiogenesis induced by subcutaneous implantation of polyether polyurethane sponge discs. Intraperitoneal (i.p.) administration of lapachol or [Bi(Lp)(2)]Cl reduced the hemoglobin
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