LAPACHOL

LAPACHOL Basic information
Product Name:LAPACHOL
Synonyms:LAPACHOL;CI 75490;NATURAL YELLOW 16;2-HYDROXY-3-(3-METHYL-2-BUTENYL)-1,4-NAPHTHOQUINONE;2-HYDROXY-3-(3-METHYLBUT-2-ENYL)-1,4-NAPHTHOQUINONE;1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-;2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione;2-hydroxy-3-(3-methyl-2-butenyl)-4-naphthoquinone
CAS:84-79-7
MF:C15H14O3
MW:242.27
EINECS:201-563-7
Product Categories:Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Anthraquinones, Hydroquinones and Quinones
Mol File:84-79-7.mol
LAPACHOL Structure
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
Colour Index 75490
pka4.81±0.10(Predicted)
form Solid
color Yellow to Dark Yellow
Merck 13,5382
InChIKeyCIEYTVIYYGTCCI-UHFFFAOYSA-N
LogP2.516 (est)
CAS DataBase Reference84-79-7
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS QL8750000
ToxicityLD50 in male, female BALB/c mice (g/kg): 0.487; 0.792 orally (Morrison)
MSDS Information
ProviderLanguage
SigmaAldrich English
LAPACHOL Usage And Synthesis
DescriptionLapachol, a benzoquinone, is a secondary allergen in teak (Tectona grandis).
OccurrenceLapacol (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.
Usesantineoplastic, antifungal
UsesIt was used in the synthesis of the lapachol metal complexes.
UsesLapachol was used in the synthesis of the lapachol metal complexes.
DefinitionChEBI: 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 DescriptionLapachol is natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.).
Biochem/physiol ActionsLapachol has antimicrobial properties against many pathogens. It has anti-inflammatory, analgesic and antibiotic properties. It is inhibitor of epithelial tumors in Drosophila melanogaster heterozygote.
Contact allergensLapachol, 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
Purification MethodsCrystallise Lapachol from pet ether/EtOH, EtOH or Et2O. [Beilstein 8 H 326, 8 I 644, 8 II 365, 8 III 2720.]
LAPACHOL Preparation Products And Raw materials
Preparation Products2-Hydroxy-3-[(E)-4-hydroxy-3-methyl-2-butenyl]-1,4-naphthoquinone
4-METHYL-1,4-HEPTADIENE 1-PHENYL-2-BUTENE LAPACHOL 3-ETHYL-2-PENTENE 1-ALLYL-2-METHYLBENZENE 3-METHYL-1-PHENYL-2-BUTENE 5-PHENYL-1-PENTENE 3-METHYL-2,5-HEXADIENE ETHYL-O-TOLYL KETONE 2-Methyl-3-(2-methylphenyl)prop-1-ene (E)-1-phenylbut-2-en-1-one LAPACHOL(RG) 3-ETHYL-3-HEXENE 1-Phenyl-2-propen-1-one TRANS-6-PHENYL-2-HEXENE 2-METHYLPHENETHYL ALCOHOL Allylacetone 1,4-DIHYDRO-NAPHTHALENE

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.