Accéder au contenu
Merck
Toutes les photos(1)

Key Documents

View All Documentation

142905

Sigma-Aldrich

Lapachol

98%

Synonyme(s) :

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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

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

Pureté

98%

Forme

solid

Pf

141-143 °C (lit.)

Solubilité

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

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

Vous recherchez des produits similaires ? Visite Guide de comparaison des produits

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Les clients ont également consulté

Slide 1 of 6

1 of 6

Plumbagin phyproof® Reference Substance

PHL80267

Plumbagin

2-Bromo-1,4-naphthoquinone 98%

Sigma-Aldrich

510300

2-Bromo-1,4-naphthoquinone

1,4-Naphthoquinone 97%

Sigma-Aldrich

152757

1,4-Naphthoquinone

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

Sigma-Aldrich

420120

Juglone

Melting point standard 283-286°C analytical standard

Supelco

67372

Melting point standard 283-286°C

Curcumin from Curcuma longa (Turmeric), powder

Sigma-Aldrich

C1386

Curcumin

Xueyin Zu et al.
Phytotherapy research : PTR, 33(9), 2337-2346 (2019-06-22)
Lapachol is a 1,4-naphthoquinone that is isolated from the Bignoniaceae family. It has been reported to exert anti-inflammatory, antibacterial, and anticancer activities. However, the anticancer activity of lapachol and its molecular mechanisms against esophageal squamous cell carcinoma (ESCC) cells have
Kenneth O Eyong et al.
Bioorganic & medicinal chemistry letters, 18(20), 5387-5390 (2008-10-03)
Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is
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.
Ingrid L Cockburn et al.
Biological chemistry, 392(5), 431-438 (2011-03-24)
Plasmodium falciparum heat shock protein 70 (PfHsp70-1) is thought to play an essential role in parasite survival and virulence in the human host, making it a potential antimalarial drug target. A malate dehydrogenase based aggregation suppression assay was adapted for
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
Afficher tous les articles scientifiques apparentés

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique