LAPACHOL Chemical Properties

Melting point:

141-143 °C(lit.)

Boiling point:

325.09°C (rough estimate)

Density 

1.2077 (rough estimate)

refractive index 

1.5740 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

ethanol: soluble10mg/mL, clear, light yellow to yellow

pka

4.81±0.10(Predicted)

form 

Solid

Colour Index 

75490

color 

Yellow to Dark Yellow

Merck 

13,5382

InChIKey

CIEYTVIYYGTCCI-UHFFFAOYSA-N

LogP

2.516 (est)

CAS DataBase Reference

84-79-7

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

QL8750000

Toxicity

LD50 in male, female BALB/c mice (g/kg): 0.487; 0.792 orally (Morrison)

MSDS

• Language:English Provider:SigmaAldrich

LAPACHOL Usage And Synthesis

Description

Lapachol, a benzoquinone, is a secondary allergen in teak (Tectona grandis).

Occurrence

Lapacol (CI Natural Yellow 16; CI 75490) (lapachic acid, taiguie acid, tecomin) is a yellow pigment occurring in the wood of trees of the genus Tecoma, native to the West Indies and tropical South America. The shavings of the wood, treated with lime water, give an extract that dyes cotton yellow.

Uses

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

Uses

antineoplastic, antifungal

Uses

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

Definition

ChEBI: Lapachol is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. It has a role as a plant metabolite, an antineoplastic agent, an antibacterial agent and an anti-inflammatory agent. It is a hydroxy-1,4-naphthoquinone and an olefinic compound.

General Description

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

Contact allergens

Lapachol, a benzoquinone, is a secondary allergen in teak (Tectona grandis L., Verbenaceae family), a wood largely used for various indoor and outdoor applications (doors, windows, etc.) because of its strong durability. It has similar reactivity to deoxylapachol. Seealso Chap. 46

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.

Purification Methods

Crystallise Lapachol from pet ether/EtOH, EtOH or Et2O. [Beilstein 8 H 326, 8 I 644, 8 II 365, 8 III 2720.]

LAPACHOL(84-79-7)Related Product Information

• 4-PENTENAL
• Allylbenzene
• Phenethyl alcohol
• Hydroxyacetone
• Allylacetone
• 1-Phenyl-2-propen-1-one
• 2-METHYL-3-PHENYL-1-PROPENE
• 2-METHYLPHENETHYL ALCOHOL
• trans-2-Pentenal
• 1,4-Naphthoquinone
• 3-ETHYL-2-PENTENE
• LAPACHOL
• 2-hydroxy-3-methyl-1,4-naphthoquinone
• Menadione
• Butyrophenone
• 2-HYDROXYACETOPHENONE
• 2-Hydroxy-1,4-naphoquinone
• 6-Methyl-5-hepten-2-one