Product Name

  • Name

    LAPACHOL

  • EINECS 201-563-7
  • CAS No. 84-79-7
  • Article Data37
  • CAS DataBase
  • Density 1.235 g/cm3
  • Solubility
  • 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
  • Appearance white to yellow powder
  • Safety 26-36
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 84-79-7 (LAPACHOL)
  • Hazard Symbols HarmfulXn
  • 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
  • PSA 54.37000
  • LogP 3.23400

Synthetic route

2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

Lapachol
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%
isonaphthazarine
605-37-8

isonaphthazarine

isoprene
78-79-5

isoprene

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With oxalic acid In 1,4-dioxane at 100℃; for 6h;78%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

prenyl bromide
870-63-3

prenyl bromide

A

Lapachol
84-79-7

Lapachol

B

2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione
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%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

prenyl bromide
870-63-3

prenyl bromide

Lapachol
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%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

prenyl bromide
870-63-3

prenyl bromide

A

Lawsone 2-isopentenyl ether
42164-69-2

Lawsone 2-isopentenyl ether

B

Lapachol
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
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0); 1-Adamantanecarboxylic acid for 1h; Heating;43%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

3-Methyl-1-butene
563-45-1

3-Methyl-1-butene

A

Lapachol
84-79-7

Lapachol

B

2-hydroxy-3-(3-methylbut-1-en-1-yl)naphthalene-1,4-dione
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%
2-hydroxy-1,4-naphthoquinone silver salt
36417-25-1

2-hydroxy-1,4-naphthoquinone silver salt

prenyl bromide
870-63-3

prenyl bromide

A

Lawsone 2-isopentenyl ether
42164-69-2

Lawsone 2-isopentenyl ether

B

Lapachol
84-79-7

Lapachol

1,2,3,4-tetrahydroxynaphthalene
5690-26-6

1,2,3,4-tetrahydroxynaphthalene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Lapachol
84-79-7

Lapachol

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

2-acetyllapachol

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With sodium carbonate
2-methoxylapachol
17241-45-1

2-methoxylapachol

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With sodium carbonate for 0.833333h; Heating;45 mg
2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
82214-83-3

2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With sodium hydroxide for 0.416667h; Heating;30 mg
3-Bromo-α-lapachone
79060-57-4

3-Bromo-α-lapachone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With acetic acid; zinc for 2h; Heating;10 mg
4-Bromo-iso-α-lapachone
79060-56-3

4-Bromo-iso-α-lapachone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With acetic acid; zinc for 2h; Heating;
4'-bromo-iso-β-lapachone
74693-34-8

4'-bromo-iso-β-lapachone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With zinc In acetic acid for 2h; Heating;40 mg
3-(2-methyl-2-buten-4-yl)-1,2-naphthalenedione
96964-75-9

3-(2-methyl-2-buten-4-yl)-1,2-naphthalenedione

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With sodium dithionite; potassium tert-butylate; oxygen 1.) benzene, 2 min, 2.) t-BuOH, 5 min.; Yield given. Multistep reaction;
1,2,4-triacetoxy-3-(3-methyl-but-2-enyl)-naphthalene
19336-09-5

1,2,4-triacetoxy-3-(3-methyl-but-2-enyl)-naphthalene

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
3'-bromo-β-lapachone
41019-50-5

3'-bromo-β-lapachone

zinc dust

zinc dust

KOH-solution

KOH-solution

Lapachol
84-79-7

Lapachol

bromo-β-lapachone

bromo-β-lapachone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With zinc
chlorodihydrolapachol

chlorodihydrolapachol

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With potassium hydroxide
prenyl bromide
870-63-3

prenyl bromide

potassium-salt of 2-hydroxy-<1,4>naphthoquinone

potassium-salt of 2-hydroxy-<1,4>naphthoquinone

A

Lawsone 2-isopentenyl ether
42164-69-2

Lawsone 2-isopentenyl ether

B

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With acetone
2-hydroxy-1,4-naphthoquinone silver salt
36417-25-1

2-hydroxy-1,4-naphthoquinone silver salt

prenyl bromide
870-63-3

prenyl bromide

A

Lapachol
84-79-7

Lapachol

B

2-<γ.γ-dimethyl-allyloxy>-naphthoquinone-(1.4)

2-<γ.γ-dimethyl-allyloxy>-naphthoquinone-(1.4)

Conditions
ConditionsYield
With diethyl ether at 0℃;
1,2,3,4-tetrahydroxynaphthalene
5690-26-6

1,2,3,4-tetrahydroxynaphthalene

isoprene
78-79-5

isoprene

A

Lapachol
84-79-7

Lapachol

B

3-hydroxy-2-<2-methyl-buten-(2)-yl>-naphthoquinone-(1.4)

3-hydroxy-2-<2-methyl-buten-(2)-yl>-naphthoquinone-(1.4)

Conditions
ConditionsYield
With 1,4-dioxane; oxalic acid und Behandeln des Reaktionsgemisches mit Luft;
2-(3-Chloro-3-methylbutyl)-3-hydroxy-1,4-naphthoquinone
111479-51-7

2-(3-Chloro-3-methylbutyl)-3-hydroxy-1,4-naphthoquinone

diluted KOH-solution

diluted KOH-solution

A

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
4707-32-8

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

B

α-lapachone
4707-33-9

α-lapachone

C

Lapachol
84-79-7

Lapachol

D

oxydihydrolapachol

oxydihydrolapachol

2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

A

Lapachol
84-79-7

Lapachol

B

2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione
64469-16-5

2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0); 1-Adamantanecarboxylic acid Heating; Title compound not separated from byproducts.;
lapachol-1,4-di-O-β-D-glucopyranoside

lapachol-1,4-di-O-β-D-glucopyranoside

A

β-D-glucose
492-61-5

β-D-glucose

B

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
With β-cellulase; water at 37℃; for 48h; Enzymatic reaction;A n/a
B 25.2 mg
2-hydroxy-3-(2-methyl-2-buten-4-yl)naphthalene
96964-74-8

2-hydroxy-3-(2-methyl-2-buten-4-yl)naphthalene

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / CuCl, O2 / acetonitrile / 0.33 h / 5 - 10 °C
2: 1.) aq. Na2S2O4, 2.) t-BuOK, O2 / 1.) benzene, 2 min, 2.) t-BuOH, 5 min.
View Scheme
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K2CO3 / acetone / 40 h / Heating
2: 70 mg / zinc dust / tetrahydrofuran / 24 h
3: 45 mg / aq.Na2CO3 / 0.83 h / Heating
View Scheme
2-chloro-1,4-naphthoquinone
1010-60-2

2-chloro-1,4-naphthoquinone

Lapachol
84-79-7

Lapachol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 300 mg / zinc dust / tetrahydrofuran / 4 h
2: 30 mg / 1percent aq.NaOH / 0.42 h / Heating
View Scheme
Lapachol
84-79-7

Lapachol

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
4707-32-8

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃;100%
With sulfuric acid at 0 - 20℃;100%
With sulfuric acid99%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

Lapachol
84-79-7

Lapachol

lapachol laurate

lapachol laurate

Conditions
ConditionsYield
With lutidine In dichloromethane at 0℃; for 0.0833333h;100%
With lutidine In dichloromethane at 0℃;100%
With triethylamine In diethyl ether at 20℃; for 0.5h;
Lapachol
84-79-7

Lapachol

2-hydroxy-3-(3-methyl-butyl)-5,6,7,8-tetrahydro-[1,4]naphthoquinone

2-hydroxy-3-(3-methyl-butyl)-5,6,7,8-tetrahydro-[1,4]naphthoquinone

Conditions
ConditionsYield
With 10% palladium on activated carbon; hydrogen; acetic acid under 2844.39 Torr; for 6h;100%
With palladium 10% on activated carbon; hydrogen; acetic acid under 2844.39 Torr; for 6h;
Lapachol
84-79-7

Lapachol

acetyl chloride
75-36-5

acetyl chloride

2-acetyllapachol
57620-99-2

2-acetyllapachol

Conditions
ConditionsYield
With lutidine In dichloromethane at 0℃; for 0.0833333h;99.7%
With lutidine In dichloromethane at 0℃;99%
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;80%
With triethylamine In diethyl ether at 20℃; for 0.5h;
Lapachol
84-79-7

Lapachol

di(4-bromophenyl) selenide
33834-56-9

di(4-bromophenyl) selenide

3-((4-bromophenyl)selanyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

3-((4-bromophenyl)selanyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 50℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry;99%
Lapachol
84-79-7

Lapachol

2-hydroxy-3-isopentylnaphthalene-1,4-dione
3343-38-2

2-hydroxy-3-isopentylnaphthalene-1,4-dione

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal under 3750.3 Torr; for 2h; Heating;98%
With 10% palladium on activated carbon; hydrogen In ethanol under 1551.49 Torr; for 0.25h;90%
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; for 12h;83%
mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)]
243643-58-5

mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)]

Lapachol
84-79-7

Lapachol

RuCl2(lapachol)(1,4-bis(diphenylphosphine)butane)
1615718-36-9

RuCl2(lapachol)(1,4-bis(diphenylphosphine)butane)

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane for 24h; Reflux; Inert atmosphere;98%
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

Lapachol
84-79-7

Lapachol

chlorido[(3-(3-methylbut-2-enyl)-2-oxo-κO)-[1,4]-naphthoquinonato-κO](η6-pentamethylcyclopentadienyl)rhodium(III)
1429209-71-1

chlorido[(3-(3-methylbut-2-enyl)-2-oxo-κO)-[1,4]-naphthoquinonato-κO](η6-pentamethylcyclopentadienyl)rhodium(III)

Conditions
ConditionsYield
With sodium methylate In methanol; dichloromethane at 20℃; for 24h; Inert atmosphere;96%
Lapachol
84-79-7

Lapachol

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromo-benzoic acid 3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalen-2-yl ester

4-bromo-benzoic acid 3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalen-2-yl ester

Conditions
ConditionsYield
With lutidine In dichloromethane at 0℃; for 0.0833333h;95.7%
Lapachol
84-79-7

Lapachol

α-lapachone
4707-33-9

α-lapachone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid95%
With hydrogenchloride; acetic acid In water95%
With hydrogenchloride In water at 80℃; for 4h;85%
Lapachol
84-79-7

Lapachol

3'-bromo-β-lapachone
41019-50-5

3'-bromo-β-lapachone

Conditions
ConditionsYield
With bromine In dichloromethane for 24h;95%
With bromine; acetic acid Behandeln des Reaktionsprodukts mit Wasser;
With chloroform; bromine Behandeln des Reaktionsprodukts mit Alkohol;
Lapachol
84-79-7

Lapachol

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

C21H18N2O
875845-30-0

C21H18N2O

Conditions
ConditionsYield
With sodium acetate; acetic acid at 90 - 95℃;95%
1-methyl-1-nitrosourea
684-93-5

1-methyl-1-nitrosourea

Lapachol
84-79-7

Lapachol

2-methoxylapachol
17241-45-1

2-methoxylapachol

Conditions
ConditionsYield
With potassium hydroxide at 0℃; Inert atmosphere;95%
Lapachol
84-79-7

Lapachol

(E)-4-(1,4-dihydro-2-hydroxy-1,4-dioxonaphthalen-3-yl)-2-methylbut-2-enal

(E)-4-(1,4-dihydro-2-hydroxy-1,4-dioxonaphthalen-3-yl)-2-methylbut-2-enal

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane Reflux;95%
isoniazid
54-85-3

isoniazid

Lapachol
84-79-7

Lapachol

1-N-isonicotinoyl-hydrazone-[2-hydroxy-3-(3-methyl-2-butenyl)]-1,4-naphthoquinone

1-N-isonicotinoyl-hydrazone-[2-hydroxy-3-(3-methyl-2-butenyl)]-1,4-naphthoquinone

Conditions
ConditionsYield
With triethylamine In water at 20℃; for 48h;95%
isoniazid
54-85-3

isoniazid

Lapachol
84-79-7

Lapachol

1-N'-(4-hydroxy-3-(3-methylbut-2-enyl)-2-oxonaphthalen-1(2H)-ylidene)isonicotinohydrazide

1-N'-(4-hydroxy-3-(3-methylbut-2-enyl)-2-oxonaphthalen-1(2H)-ylidene)isonicotinohydrazide

Conditions
ConditionsYield
Stage #1: isoniazid; Lapachol With triethylamine In water at 20℃; for 48h;
Stage #2: With acetic acid In water
95%
cis-[RuCl2(triphenylphospine)2(1,10-phenantroline)]
159700-02-4, 21627-33-8

cis-[RuCl2(triphenylphospine)2(1,10-phenantroline)]

Lapachol
84-79-7

Lapachol

hexafluorophosphate

hexafluorophosphate

[Ru(lapachol)(triphenylphospine)2(1,10-phenantroline)]PF6

[Ru(lapachol)(triphenylphospine)2(1,10-phenantroline)]PF6

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane for 72h; Reflux; Inert atmosphere;94%
Di-n-butyl selenide
14835-66-6

Di-n-butyl selenide

Lapachol
84-79-7

Lapachol

3-(butylselanyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

3-(butylselanyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 50℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry;94%
Lapachol
84-79-7

Lapachol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

3-(3-methylbut-2-enyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl methanesulfonate
1376687-04-5

3-(3-methylbut-2-enyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl methanesulfonate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 0 - 20℃; for 48h;93.7%
Lapachol
84-79-7

Lapachol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C21H28O3Si

C21H28O3Si

Conditions
ConditionsYield
With lutidine In dichloromethane at 0℃;93%
diphenyl diselenide
1666-13-3

diphenyl diselenide

Lapachol
84-79-7

Lapachol

2,2-dimethyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

2,2-dimethyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V) In acetonitrile at 20℃; for 1h; Reagent/catalyst; Solvent; Time; Electrolysis; Green chemistry;93%
With iodine; dimethyl sulfoxide In neat (no solvent) at 50℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry; regioselective reaction;65%
With iodine; dimethyl sulfoxide at 50℃; for 0.166667h; Microwave irradiation;
4,7-dichloroquinoline
86-98-6

4,7-dichloroquinoline

Lapachol
84-79-7

Lapachol

2-((7-chloroquinolin-4- yl)oxy)-3-(3-methylbut-2- en- 1-yl)naphthalene-1,4- dione

2-((7-chloroquinolin-4- yl)oxy)-3-(3-methylbut-2- en- 1-yl)naphthalene-1,4- dione

Conditions
ConditionsYield
Stage #1: Lapachol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 4,7-dichloroquinoline In N,N-dimethyl-formamide at 120℃; for 24h;
93%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

Lapachol
84-79-7

Lapachol

chlorido[(3-(3-methylbut-2-enyl)-2-oxo-κO)-[1,4]-naphthoquinonato-κO](η6-p-cymene)ruthenium(II)
1429209-69-7

chlorido[(3-(3-methylbut-2-enyl)-2-oxo-κO)-[1,4]-naphthoquinonato-κO](η6-p-cymene)ruthenium(II)

Conditions
ConditionsYield
With sodium methylate In methanol; dichloromethane at 20℃; for 4.5h; Inert atmosphere;92%
Lapachol
84-79-7

Lapachol

dimethyl sulfate
77-78-1

dimethyl sulfate

2-methoxylapachol
17241-45-1

2-methoxylapachol

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 3h;91%
With potassium carbonate In acetone at 20℃; for 2h;88%
With sodium hydroxide at 70 - 80℃; for 1h;139 mg
With potassium carbonate In acetone
With potassium carbonate In acetone at 20℃;
Lapachol
84-79-7

Lapachol

3-hydroxy-4-(hydroxyimino)-2-(3-methylbut-2-enylnaphtalen-1(4H)-one)

3-hydroxy-4-(hydroxyimino)-2-(3-methylbut-2-enylnaphtalen-1(4H)-one)

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride for 2h;91%
Lapachol
84-79-7

Lapachol

2-bis[3,5bis(trifluoromethyl)phenyl]diselane
1787-80-0

2-bis[3,5bis(trifluoromethyl)phenyl]diselane

2,2-dimethyl-3-(naphthalen-1-ylselanyl)-3,4-dihydro-2Hbenzo[h]chromene-5,6-dione

2,2-dimethyl-3-(naphthalen-1-ylselanyl)-3,4-dihydro-2Hbenzo[h]chromene-5,6-dione

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V) In acetonitrile at 20℃; for 1h; Electrolysis; Green chemistry;91%
Lapachol
84-79-7

Lapachol

2,3-dihydro-3-[(3-methylbut-2-enyl)-1,4-naphthoquinon-2-yloxy]-3-(3-methylbut-2-enyl)-2-oxo-1,4-naphthoquinone
855637-05-7

2,3-dihydro-3-[(3-methylbut-2-enyl)-1,4-naphthoquinon-2-yloxy]-3-(3-methylbut-2-enyl)-2-oxo-1,4-naphthoquinone

Conditions
ConditionsYield
With lead dioxide In acetic acid Heating;90%
With lead dioxide; acetic acid90%
With lead dioxide; acetic acid Heating;
Lapachol
84-79-7

Lapachol

(E)-2-hydroxy-3-(4-hydroxy-3-methylbut-2-enyl)-naphthalene-1,4-dione
523-34-2

(E)-2-hydroxy-3-(4-hydroxy-3-methylbut-2-enyl)-naphthalene-1,4-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; selenium(IV) oxide; salicylic acid In dichloromethane at 0 - 20℃; for 2h;90%
Multi-step reaction with 2 steps
1: selenium(IV) oxide / 1,4-dioxane / Reflux
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
View Scheme
Lapachol
84-79-7

Lapachol

A

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
4707-32-8

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

B

α-lapachone

α-lapachone

Conditions
ConditionsYield
With zinc(II) chloride In dichloromethane at 42℃; for 4h; Reagent/catalyst; Temperature;A n/a
B 90%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

cobalt(II) acetate dihydrate

cobalt(II) acetate dihydrate

Lapachol
84-79-7

Lapachol

[Co(lapachol)2(1,10-phenanthroline)]

[Co(lapachol)2(1,10-phenanthroline)]

Conditions
ConditionsYield
Stage #1: Lapachol With potassium hydroxide In methanol for 1h;
Stage #2: 1,10-Phenanthroline; cobalt(II) acetate dihydrate In methanol at 20℃; for 3h;
89.3%

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 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.

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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