142905

Sigma-Aldrich

Lapachol

98%

Synonym(s):
Natural Yellow 16, 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
Empirical Formula (Hill Notation):
C15H14O3
CAS Number:
Molecular Weight:
242.27
Colour Index Number:
75490
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

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.

Packaging

250 mg in glass insert

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

20/21/22-36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Cristian Salas et al.
Bioorganic & medicinal chemistry, 16(2), 668-674 (2007-11-22)
Derivatives of natural quinones with biological activities, such as lapachol, alpha- and beta-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi cells. All tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar...
Ricardo Vessecchi et al.
Journal of mass spectrometry : JMS, 47(12), 1648-1659 (2013-01-03)
In order to understand the influence of alkyl side chains on the gas-phase reactivity of 1,4-naphthoquinone derivatives, some 2-hydroxy-1,4-naphthoquinone derivatives have been prepared and studied by electrospray ionization tandem mass spectrometry in combination with computational quantum chemistry calculations. Protonation and...
Lu Bai et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 944, 128-135 (2013-12-10)
Lapachol is a natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.) that possesses a range of significant biological activities. Nine phase I and four phase II metabolites of lapachol in rat bile were firstly elucidated and identified using a sensitive...
Eduardo J S Salustiano et al.
Investigational new drugs, 28(2), 139-144 (2009-03-04)
The pentacyclic 1,4-naphthoquinones 1a-d were cytotoxic (IC(50) approximately 2-7 microM) to human leukemic cell lines K562 (oxidative stress-resistant), Lucena-1 (MDR phenotype) and Daudi. Fresh leukemic cells obtained from patients, some with the MDR phenotype, were also sensitive to these compounds....
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....

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