142905
Lapachol
98%
Synonym(s):
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone, Natural Yellow 16
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About This Item
Empirical Formula (Hill Notation):
C15H14O3
CAS Number:
Molecular Weight:
242.27
Colour Index Number:
75490
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
solid
mp
141-143 °C (lit.)
solubility
ethanol: soluble 10 mg/mL, clear, light yellow to yellow
functional group
ketone
SMILES string
C\C(C)=C\CC1=C(O)C(=O)c2ccccc2C1=O
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
InChI key
CIEYTVIYYGTCCI-UHFFFAOYSA-N
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General description
Lapachol is natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.).
Application
Lapachol was used in the synthesis of the lapachol metal complexes.
Biochem/physiol Actions
Lapachol has antimicrobial properties against many pathogens. It has anti-inflammatory, analgesic and antibiotic properties. It is inhibitor of epithelial tumors in Drosophila melanogaster heterozygote.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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.
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
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
Ricardo Vessecchi et al.
Rapid communications in mass spectrometry : RCM, 24(14), 2101-2108 (2010-06-17)
Electrospray ionization mass spectrometric analysis of lapachol (2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone) was accomplished in order to elucidate the gas-phase dissociation reactions of this important biologically active natural product. The occurrence of protonated and cationized species in the positive mode and of deprotonated species
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