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142905

Lapachol

Name: Lapachol
Brand: ALDRICH

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

PubChem Substance ID:

24848565

UNSPSC Code:

12352100

Colour Index Number:

75490

NACRES:

NA.22

EC Number:

201-563-7

MDL number:

MFCD00001679

Assay:

98%

Form:

solid

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Properties

Quality Level

100

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

Description

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.

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

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

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The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages.

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

Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.

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

Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: a computational and mass spectrometry study of lapachol congeners.

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

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Global Trade Item Number

SKU	GTIN
291811-100ML	04061826594308
291811-500ML	04061837404917
142905-250MG	04061838734532