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142905

Sigma-Aldrich

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:
84-79-7
Molecular Weight:
242.27
Colour Index Number:
75490
EC Number:
201-563-7
MDL number:
MFCD00001679
UNSPSC Code:
12352100
PubChem Substance ID:
24848565
NACRES:
NA.22

Assay

98%

form

solid

mp

141-143 °C (lit.)

solubility

ethanol: soluble 10 mg/mL, clear, light yellow to yellow

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Renato A S Oliveira et al.
International immunopharmacology, 10(11), 1463-1473 (2010-09-15)
The present study reports the anti-mycobacterial activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol) as well as its influence on macrophage functions. Lapachol (L) did not induce apoptosis/necrosis of THP-1 macrophages at ≤32 μg/mL. Mycobacterium avium liquid growth was arrested by ≥32 μg/mL and
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