| Identification | Back Directory | [Name]
LAPACHOL | [CAS]
84-79-7 | [Synonyms]
Tecomin
LAPACHOL
CI 75490
taiguwood
NSC 11905
nsc-11905
Taigu Wood
taiguicacid
Greenharten
Greenhartin
Groenhartin
Lapachol 98%
Taiquic acid
Taiguic acid
lapacholwood
lapachicacid
Lapachol Wood
Lapachic acid
bethabarrawood
Lapachoic acid
Lapachol, >=99%
Bethabarra Wood
ipe-tobaccowood
Ipe-Tobacco Wood
Zlut prirodni 16
Lapachol,CI 75490
NATURAL YELLOW 16
c.i.naturalyellow16
surinamgreenheartwood
C.I. Natural Yellow 16
Surinam Greenheart Wood
2-Hydroxy-3-(3-methyl-2-butenyl)naphthoquinone
2-hydroxy-3-(3-methyl-2-butenyl)-4-naphthoquinone
2-HYDROXY-3-(3-METHYL-2-BUTENYL)-1,4-NAPHTHOQUINONE
2-HYDROXY-3-(3-METHYLBUT-2-ENYL)-1,4-NAPHTHOQUINONE
4-hydroxy-3-(3-methylbut-2-enyl)-1,2-naphthoquinone
4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
2-hydroxy-3-(3-Methylbut-2-en-1-yl)naphthalene-1,4-dione
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone, Natural Yellow16 | [EINECS(EC#)]
201-563-7 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD00001679 | [MOL File]
84-79-7.mol | [Molecular Weight]
242.27 |
| Chemical Properties | Back Directory | [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 | [form ]
Solid | [pka]
4.81±0.10(Predicted) | [color ]
Yellow to Dark Yellow | [Merck ]
13,5382 | [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 | [InChIKey]
CIEYTVIYYGTCCI-UHFFFAOYSA-N | [LogP]
2.516 (est) | [CAS DataBase Reference]
84-79-7 |
| Hazard Information | Back Directory | [Uses]
antineoplastic, antifungal | [Uses]
It was used in the synthesis of the lapachol metal complexes. | [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. | [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.). | [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. | [storage]
Store at -20°C | [Purification Methods]
Crystallise Lapachol from pet ether/EtOH, EtOH or Et2O. [Beilstein 8 H 326, 8 I 644, 8 II 365, 8 III 2720.] |
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