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Cas Database |
| Name |
Lapachol |
EINECS | 201-563-7 |
| CAS No. | 84-79-7 | Density | 1.235 g/cm3 |
| PSA | 54.37000 | LogP | 3.23400 |
| Solubility | N/A | Melting Point |
141-143 ºC(lit.) |
| Formula | C15H14 O3 | Boiling Point | 398.6 ºC at 760 mmHg |
| Molecular Weight | 242.274 | Flash Point | 209 ºC |
| Transport Information | N/A | Appearance | white to yellow powder |
| Safety | 26-36 | Risk Codes | 20/21/22-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xn
|
| Synonyms |
1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-butenyl)- (9CI); 1,4-Naphthoquinone,2-hydroxy-3-(3-methyl-2-butenyl)- (7CI,8CI); Lapachol (6CI);2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione;2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone; Bethabarra Wood; C.I.75490; C.I. Natural Yellow 16; Greenhartin; Ipe-tobacco Wood; Lapachol Wood;NSC 11905; NSC 629756; Surinam Greenheart Wood; Taigu Wood; Taiguic acid;Tecomin |
Article Data | 37 |
Lapachol Synthetic route
| Conditions | Yield |
|---|---|
| With formic acid In ethanol; water at 200℃; under 155.149 - 155149 Torr; for 3h; chemoselective reaction; | 78% |
| With formic acid In ethanol; water at 200℃; for 3h; | 78% |
| Conditions | Yield |
|---|---|
| With oxalic acid In 1,4-dioxane at 100℃; for 6h; | 78% |
- 83-72-7
2-Hydroxy-1,4-naphthoquinone
- 870-63-3
prenyl bromide
A
- 84-79-7
Lapachol
B
- 64469-16-5
2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione
| Conditions | Yield |
|---|---|
| With tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,4-dioxane at 20℃; for 4h; Heck Reaction; | A 61% B 16% |
| Conditions | Yield |
|---|---|
| With triethylamine; sodium iodide In dimethyl sulfoxide at 20 - 70℃; for 7h; Inert atmosphere; | 60% |
| With tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,4-dioxane at 20℃; for 4h; Heck Reaction; | 23% |
| With lead(II) bromide; aluminium In acetonitrile for 15h; | 20% |
- 83-72-7
2-Hydroxy-1,4-naphthoquinone
- 870-63-3
prenyl bromide
A
- 42164-69-2
Lawsone 2-isopentenyl ether
B
- 84-79-7
Lapachol
| Conditions | Yield |
|---|---|
| With triethylamine; sodium iodide In N,N-dimethyl-formamide at 40℃; for 72h; | A 4.8% B 58.2% |
| With lithium hydride In dimethyl sulfoxide 45 deg C, 5 h; 25 deg C, 10 h; | A 30% B 40% |
| With zinc In tetrahydrofuran at 55 - 60℃; for 3h; Further byproducts given; | A 0.2 B 150 mg |
| Conditions | Yield |
|---|---|
| tetrakis(triphenylphosphine) palladium(0); 1-Adamantanecarboxylic acid for 1h; Heating; | 43% |
- 83-72-7
2-Hydroxy-1,4-naphthoquinone
- 563-45-1
3-Methyl-1-butene
A
- 84-79-7
Lapachol
B
- 4042-39-1
2-hydroxy-3-(3-methylbut-1-en-1-yl)naphthalene-1,4-dione
| Conditions | Yield |
|---|---|
| With copper diacetate; sodium acetate; palladium diacetate In tetrahydrofuran at 20℃; for 3h; Mechanism; Catalytic behavior; | A 20% B 33% |
- 36417-25-1
2-hydroxy-1,4-naphthoquinone silver salt
- 870-63-3
prenyl bromide
A
- 42164-69-2
Lawsone 2-isopentenyl ether
B
- 84-79-7
Lapachol
| Conditions | Yield |
|---|---|
| With 1,4-dioxane; oxalic acid und Behandeln des Reaktionsgemisches mit Luft; |
- 57620-99-2
2-acetyllapachol
- 84-79-7
Lapachol
| Conditions | Yield |
|---|---|
| With sodium carbonate |
Lapachol Chemical Properties
Molecular Structure of Lapachol (CAS NO.84-79-7):
EINECS: 201-563-7
IUPAC Name: 4-Hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
Molecular Formula: C15H14O3
Molecular Weight: 242.269860 g/mol
XLogP3-AA: 2.8
H-Bond Donor: 1
H-Bond Acceptor: 3
Canonical SMILES: CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
InChI: InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3
InChIKey: CWPGNVFCJOPXFB-UHFFFAOYSA-N
Index of Refraction: 1.606
Molar Refractivity: 67.61 cm3
Molar Volume: 196 cm3
Surface Tension: 51.1 dyne/cm
Density: 1.235 g/cm3
Flash Point: 203.9 °C
Enthalpy of Vaporization: 67.46 kJ/mol
Boiling Point: 390.1 °C at 760 mmHg
Vapour Pressure: 8.73E-07 mmHg at 25 °C
Melting Point: 141-143 °C(lit.)
Water Solubility: 55.6 mg/L at 25 °C
BRN: 2051889
Lapachol Toxicity Data With Reference
| 1. | orl-rat LDLo:1200 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 17 (1970),1. | ||
| 2. | orl-mus LD50:487 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 17 (1970),1. | ||
| 3. | ipr-mus LD50:400 mg/kg | JMCMAR Journal of Medicinal Chemistry. 26 (1983),570. |
Lapachol Safety Profile
Safety Information of Lapachol (CAS NO.84-79-7):
Hazard Codes: Xn 
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
WGK Germany: 3
RTECS: QL8750000
Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and fumes.
Lapachol Specification
Lapachol with CAS registry number of 84-79-7 is also known as 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione ; 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone ; 4-08-00-02487 (Beilstein Handbook Reference) ; Bethabarra wood ; C.I. 75490 ; C.I. Natural Yellow 16 ; CCRIS 745 ; Greenharten ; Greenhartin ; IPE-tobacco wood ; Lapachic acid ; Lapachol wood ; Surinam greenheart wood ; Taigu wood ; Taiguic acid ; Tecomin ; Tecomin (VAN) ; Zlut prirodni 16 ; Zlut prirodni 16 [Czech] ; 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)- (9CI) ; 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)- . It can be isolated from the lapacho tree.
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