Basic information
- CAS
84-79-7- Standard SMILES
CC(C)=CCC1=C(O)c2ccccc2C(=O)C1=O- InChIKey
CIEYTVIYYGTCCI-UHFFFAOYSA-N- Molecular formula
- C15H14O3
- Average molar mass
- 242.27 g/mol
- Monoisotopic mass
- 242.0942943
Overview
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 an antibacterial agent, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a hydroxy-1,4-naphthoquinone and an olefinic compound.
Names & identifiers
- Preferred name
- Npc216413
- IUPAC
- 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
- English name
- LAPACHOL
- Molecular formula
- C15H14O3
- Molecular weight
- 242.27
Names & synonyms
RefChem:1092886Npc216413lapachol84-79-7GreenhartinBethabarra woodTaiguic acidLapachic acidLapachol woodC.I. Natural Yellow 16Taigu woodIPE-tobacco wood
Show more names
TecominCI 75490taiguwoodGroenhartin
Greenharten2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dioneSurinam greenheart woodNSC-11905C.I. 75490Zlut prirodni 164-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dioneNSC 11905
Database identifiers
- CAS
84-79-7- PubChem CID
- 3884
- DTXSID
DTXSID6049430- ChEMBL
CHEMBL15193- ChEBI
CHEBI:6377- UNII
- B221938VB6
- Nikkaji
- J1.467.697J、J4.900J
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 439
Experimental & physicochemical properties
Collision Cross Section145.11 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 141 · 141-143 °C(lit.)
- Boiling point
- 325.09 °C · 325.09°C (rough estimate)
- Density
- 1.2077 · 1.2077 (rough estimate)
- refractive index
- 1.574 · 1.5740 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 10 mg/mL, · ethanol: soluble10mg/mL, clear, light yellow to yellow
- pka
- 4.81 · 4.81±0.10(Predicted)
- form
- Solid
- Colour Index
- 75490 · 75490
- color
- Yellow to Dark Yellow
- Merck
- 13 · 13,5382
- Cosmetics Ingredients Functions
- SKIN PROTECTINGANTIOXIDANT
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- QL8750000
- Toxicity
- LD50 in male, female BALB/c mice (g/kg): 0.487; 0.792 orally (Morrison)
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Applications
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.
UsesLapachol was used in the synthesis of the lapachol metal complexes.
Usesantineoplastic, antifungal
UsesIt was used in the synthesis of the lapachol metal complexes.
General DescriptionLapachol is natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
Related reactions
0 records
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Compound notes
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