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Basic Information
CAS No.: 84-79-7
Name: LAPACHOL
Article Data: 37
Molecular Structure:
Molecular Structure of 84-79-7 (LAPACHOL)
Formula: C15H14 O3
Molecular Weight: 242.274
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
EINECS: 201-563-7
Density: 1.235 g/cm3
Melting Point: 141-143 ºC(lit.)
Boiling Point: 398.6 ºC at 760 mmHg
Flash Point: 209 ºC
Appearance: white to yellow powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 26-36
PSA: 54.37000
LogP: 3.23400
Synthetic route
83-72-7

2-Hydroxy-1,4-naphthoquinone

107-86-8

3,3-dimethyl acrylaldehyde

84-79-7

Lapachol

Conditions
ConditionsYield
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%
605-37-8

isonaphthazarine

78-79-5

isoprene

84-79-7

Lapachol

Conditions
ConditionsYield
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
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,4-dioxane at 20℃; for 4h; Heck Reaction;A 61%
B 16%
83-72-7

2-Hydroxy-1,4-naphthoquinone

870-63-3

prenyl bromide

84-79-7

Lapachol

Conditions
ConditionsYield
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
ConditionsYield
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
83-72-7

2-Hydroxy-1,4-naphthoquinone

556-82-1

3-methyl-2-buten-1-ol

84-79-7

Lapachol

Conditions
ConditionsYield
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
ConditionsYield
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

5690-26-6

1,2,3,4-tetrahydroxynaphthalene

556-82-1

3-methyl-2-buten-1-ol

84-79-7

Lapachol

Conditions
ConditionsYield
With 1,4-dioxane; oxalic acid und Behandeln des Reaktionsgemisches mit Luft;
57620-99-2

2-acetyllapachol

84-79-7

Lapachol

Conditions
ConditionsYield
With sodium carbonate
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Chemistry

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

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.

Safety Profile

Safety Information of Lapachol (CAS NO.84-79-7):
Hazard Codes: Xn Harmful
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.

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.