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142905

Sigma-Aldrich

Lapachol

98%

Synonyme(s) :

2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone, Natural Yellow 16

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About This Item

Formule empirique (notation de Hill):
C15H14O3
Numéro CAS:
84-79-7
Poids moléculaire :
242.27
Numéro C.I. (Colour Index):
75490
Numéro CE :
201-563-7
Numéro MDL:
MFCD00001679
Code UNSPSC :
12352100
ID de substance PubChem :
24848565
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Forme

solid

Pf

141-143 °C (lit.)

Solubilité

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

Groupe fonctionnel

ketone

Chaîne SMILES 

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

Clé InChI

CIEYTVIYYGTCCI-UHFFFAOYSA-N

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Description générale

Lapachol is natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.).

Application

Lapachol was used in the synthesis of the lapachol metal complexes.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Conseils de prudence

P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
SHBN9242
SHBN4964
SHBM9233
SHBL8651
00509KNV

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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
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
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.
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
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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