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142905

Sigma-Aldrich

Lapachol

98%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C15H14O3
CAS-Nummer:
84-79-7
Molekulargewicht:
242.27
Farbindexnummer:
75490
EG-Nummer:
201-563-7
MDL-Nummer:
MFCD00001679
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24848565
NACRES:
NA.22

Assay

98%

Form

solid

mp (Schmelzpunkt)

141-143 °C (lit.)

Löslichkeit

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

InChIKey

CIEYTVIYYGTCCI-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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

Biochem./physiol. Wirkung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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PHL80267

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2-Brom-1,4-naphthochinon 98%

Sigma-Aldrich

510300

2-Brom-1,4-naphthochinon

1,4-Naphthochinon 97%

Sigma-Aldrich

152757

1,4-Naphthochinon

Juglon A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).

Sigma-Aldrich

420120

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Schmelzpunktstandard 283-286°C analytical standard

Supelco

67372

Schmelzpunktstandard 283-286°C

Curcumin from Curcuma longa (Turmeric), powder

Sigma-Aldrich

C1386

Curcumin

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.
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
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
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
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