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142905

Sigma-Aldrich

Lapachol

98%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C15H14O3
Numero CAS:
84-79-7
Peso molecolare:
242.27
Colour Index:
75490
Numero CE:
201-563-7
Numero MDL:
MFCD00001679
Codice UNSPSC:
12352100
ID PubChem:
24848565
NACRES:
NA.22

Livello qualitativo

100

Saggio

98%

Stato

solid

Punto di fusione

141-143 °C (lit.)

Solubilità

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

Gruppo funzionale

ketone

Stringa SMILE

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
CIEYTVIYYGTCCI-UHFFFAOYSA-N

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Descrizione generale

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

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302

Consigli di prudenza

P301 + P312 + P330

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

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Certificati d'analisi (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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