3568-90-9

Usage

Uses

Used in Woodworking Industry:
Deoxylapachol is used as an allergen in the woodworking industry, specifically associated with teak wood (Tectona grandis). It is important for workers in this industry to be aware of the potential sensitization and allergic reactions that may occur due to exposure to deoxylapachol.
Used in Allergen Research:
Deoxylapachol is used as a subject of study in allergen research to better understand its effects on human health and to develop strategies for minimizing sensitization and allergic reactions among those exposed to it, such as woodworkers and individuals working with teak wood.
Used in Occupational Health and Safety:
Deoxylapachol is used as a reference allergen in occupational health and safety guidelines and regulations, helping to establish safety measures and protocols for workers who may come into contact with teak wood and are at risk of sensitization or allergic reactions.

Contact allergens

Deoxylapachol is the main allergen identified in teak (Tectona grandis). Sensitization often concerns people involved in woodwork.

InChI:InChI=1/C15H14O2/c1-10(2)7-8-11-9-14(16)12-5-3-4-6-13(12)15(11)17/h3-7,9H,8H2,1-2H3

Synthetic route

(1R*,4S*,4aR*,9aS*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione + (1R*,4S*,4aS*,9aR*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione → deoxylapachol (3568-90-9)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Inert atmosphere; Reflux;	98%

(3-methyl-2-butenyl)trifluorosilane (114067-34-4) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9)

Conditions	Yield
With iron(III) chloride In formamide for 24h; Ambient temperature;	96%
With iron(III) chloride In N,N-dimethyl-formamide; acetonitrile at 20℃;	96%

1,4-dimethoxy-2-(3-methyl-2-butenyl)-naphthalene (137414-53-0) → deoxylapachol (3568-90-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.25h;	92%

2-chloro-1,4-naphthoquinone (1010-60-2) + prenylindium sesquibromide → deoxylapachol (3568-90-9) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
In N,N-dimethyl-formamide at -23℃; for 3h;	A 53% B 37%

4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane (141550-13-2) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9)

Conditions	Yield
In chloroform-d1 at 20℃; for 24h; Inert atmosphere;	53%

prenyl bromide (870-63-3) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9)

Conditions	Yield
With lead(II) bromide; aluminium In acetonitrile for 10h;	50%
With zinc In tetrahydrofuran at 55 - 60℃; for 1.5h; Further byproducts given;	500 mg

(3-methyl-2-butenyl)trifluorosilane (114067-34-4) + [1,4]naphthoquinone (130-15-4) → 1,4-Dihydroxynaphthalene (571-60-8) + deoxylapachol (3568-90-9) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;	A 38% B 28% C 32%

[1,4]naphthoquinone (130-15-4) → 1,4-Dihydroxynaphthalene (571-60-8) + deoxylapachol (3568-90-9) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
With (3-methyl-2-butenyl)trifluorosilane; tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;	A 38% B 28% C 32%

tricarbonyl<4-methoxy-2(3)-(3-methyl-2-butenyl)-1-naphthol>chromium(0) → deoxylapachol (3568-90-9)

Conditions	Yield
With silver(l) oxide	38%

4-methyl-pent-3-enoic acid (504-85-8) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9) + 2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (58880-17-4)

Conditions	Yield
With ammonium persulfate; silver nitrate In water; acetonitrile at 65 - 70℃; for 6h;	A 35% B 8%

2-chloro-1,4-naphthoquinone (1010-60-2) + prenyl bromide (870-63-3) → deoxylapachol (3568-90-9) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
With indium(III) chloride; water; zinc In tetrahydrofuran for 4h; Ambient temperature;	A 32% B 14%

1,4-Dihydroxynaphthalene (571-60-8) + 2-methyl-3-buten-2-ol (115-18-4) → deoxylapachol (3568-90-9)

Conditions	Yield
(i) BF3*Et2O, dioxane, (ii) Ag2O, Et2O; Multistep reaction;

4-methyl-pent-3-enoic acid (504-85-8) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate

2-chloro-1,4-naphthoquinone (1010-60-2) + prenyl bromide (870-63-3) → deoxylapachol (3568-90-9) + 2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (82214-83-3) + 2-chloro-2,3-dihydro-3,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (82214-85-5)

Conditions	Yield
With zinc In tetrahydrofuran for 4h; Further byproducts given;	A 20 mg B 300 mg C 0.3 (unit not given)
With zinc In tetrahydrofuran for 4h; Further byproducts given;	A 20 mg B 300 mg C 0.3

prenyl bromide (870-63-3) + [1,4]naphthoquinone (130-15-4) → deoxylapachol (3568-90-9) + 2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (58880-17-4) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
With zinc In tetrahydrofuran at 55 - 60℃; for 4h;	A 20 mg B 400 mg C 1.2 (unit not given)
With zinc In tetrahydrofuran at 55 - 60℃; for 4h;	A 20 mg B 400 mg C 1.2

1,4-Dihydroxynaphthalene (571-60-8) + 3-methyl-2-buten-1-ol (556-82-1) → deoxylapachol (3568-90-9)

Conditions	Yield
(i) BF3-Et2O, dioxane, (ii) Ag2O, MgSO4, Et2O; Multistep reaction;

catalponol (34168-56-4, 57231-36-4, 70368-23-9) → deoxylapachol (3568-90-9)

Conditions	Yield
With manganese(IV) oxide In benzene

[1,4]naphthoquinone (130-15-4) + 1.) prenylindium sequibromide → deoxylapachol (3568-90-9) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
With sodium sulfate; silver(l) oxide 1.) DMF, -23 deg C, 3 h, 2.) Et2O, reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

deoxylapachol (3568-90-9) + prenylindium sesquiiodide → (Z)-2,3-benzo-5-methyl-5-(3,7-dimethylocta-2,6-dienyl)cyclohexane-1,4-dione (137554-07-5) + 2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone (82214-84-4)

Conditions	Yield
In N,N-dimethyl-formamide at -23℃; for 3h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 100%

deoxylapachol (3568-90-9) → 2-(3-methyl-but-2-enyl)-2,3-epoxy-1,4-naphthoquinone (137492-06-9)

Conditions	Yield
With dihydrogen peroxide; sodium carbonate In water; acetone at 0℃;	82%

deoxylapachol (3568-90-9) → 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (4707-32-8)

Conditions	Yield
With iron(III) chloride; toluene-4-sulfonic acid In water; toluene at 90℃; for 0.5h; Reagent/catalyst; Solvent;	76%

deoxylapachol (3568-90-9) → hemitectol (1187181-61-8)

Conditions	Yield
With pyridine for 24h; Reflux; Inert atmosphere;	75%

deoxylapachol (3568-90-9) → (+)-2-(3-Methyl-2-butenyl)-1,4-naphthoquinone 2,3-epoxide (73377-79-4)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; N-benzylcinchonidinum chloride In water; toluene at 35 - 40℃;	53%

deoxylapachol (3568-90-9) → 1.4-Dihydroxy-2-(3-methyl-buten-(2)-yl)-naphthalin (90685-35-1)

Conditions	Yield
(i) SnCl2, aq. HCl, dioxane, (ii) ZnCl2; Multistep reaction;

deoxylapachol (3568-90-9) + acetic anhydride (108-24-7) → 2-(γ,γ-Dimethylallyl)-naphthohydrochinon-1,4-diacetat (17532-55-7)

Conditions	Yield
With sodium acetate; zinc Heating;

deoxylapachol (3568-90-9) → 2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone (909576-31-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;

deoxylapachol (3568-90-9) → 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol (645413-83-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating View Scheme

deoxylapachol (3568-90-9) → 5-bromo-6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran (909576-35-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating 4.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 5.1: pyridine / 16 h / 20 °C 6.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C View Scheme

Upstream product

• 571-60-8 1,4-Dihydroxynaphthalene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 870-63-3 prenyl bromide 
• 556-82-1 3-methyl-2-buten-1-ol 
• 130-15-4 [1,4]naphthoquinone 
• 141550-13-2 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane 
• 137414-53-0 1,4-dimethoxy-2-(3-methyl-2-butenyl)-naphthalene 
• 504-85-8 4-methyl-pent-3-enoic acid 
• 34168-56-4 catalponol 
• 114067-34-4 (3-methyl-2-butenyl)trifluorosilane 

Downstream Products

• 55481-88-4 mollugin 
• 573-13-7 lapachenole 
• 137492-06-9 2-(3-methyl-but-2-enyl)-2,3-epoxy-1,4-naphthoquinone 
• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 909576-34-7 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran 

Relevant academic research and scientific papers

Synthesis of β-lapachone, a potential anticancer agent from the lapacho tree

A pharmaceutically important natural product, β-lapachone, was efficiently synthesized in four steps in 70% overall yield starting from commercially available 1, 4-naphthoquinone. The key step of the synthesis was the direct conversion of 2-prenyl-1, 4-naphthoquinone into β-lapachone through an advantageous cyclization/hydration/oxidation cascade process.

Direct allylation of quinones with allylboronates

Allylboronates undergo C-H allylation of unsubstituted or monosubstituted benzoquinone and naphthoquinone substrates. In the case of 2,5-or 2,6-disubstituted quinones addition involving the substituted carbon takes place. Allylation with stereodefined allylboronates occurs with retention of the configuration.

Synthesis and cytotoxicity of analogues of the marine secondary metabolite, 2-deoxylapachol

The syntheses of four 2-substituted 1,4 naphthoquinones, related to the marine natural product 2-deoxylapachol, are reported. All four synthetic compounds were cytotoxic to WHCO1 oesophageal cancer cells.

Synthesis of mollugin

The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented.

Allylation of quinones with allyl (trifluoro)silanes: Direct synthesis of isoprenoid quinones

Allylation of a variety of quinones with allyl(trifluoro)silanes takes place with high regioselectivity in the presence of FeCl3·6H2O, giving allylquinones in good yields. This method was used to synthesize biologically active isoprenoid quinones such as plastoquinone-1 and vitamin K1.

Process for the preparation of a quinone derivative

Disclosed herein are a quinone derivative represented by the following formula: STR1 wherein E1 and E2 are identical with or different from each other and mean individually a lower alkyl or lower alkoxy group, or may form an aromatic ring together, E3 denotes a lower alkyl group, n stands for 0 or an integer of 1-9, and a linkage ------ is a single or double bond, such as a vitamin K derivative or coenzyme Q derivative; and a process for the preparation of the quinone derivative at a high yield without forming any geometric isomer; as well as a 1,4,4a,8a -tetrahydro-4a α-alkenyl-1α,4α-methanonaphthalene-5,8-dione derivative which is useful as an intermediate for the preparation of the quinone derivative.

Allylation of Carbonyl Compounds with Catalytic Amount of Indium

Allylation of aldehyde and ketone, and prenylation of 2-chlorobenzoquinone were achieved by using a combination of a catalytic amount of indium(III) chloride and metallic aluminium or zinc.

Allylation of quinones bu allylic indium reagents

Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.

Prenylation of Quinonoid Compounds with Prenyl Bromide Using Lead Bromide/Aluminium Powder as Catalyst

An efficient method for the prenylation at quinonoid position using prenyl bromide in the presence of catalytic amount of lead bromide and aluminium powder in acetonitrile has been carried out.

Synthesis of Naturally Occuring Naphthoquinones: Deoxylapachol, 2,3-Di-(3-methyl-but-2-enyl)-1,4-naphthoquinone, 2-Methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone and Lapachol

Deoxylapachol (I), 2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (II), 2-methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone (III) and lapachol (IV) have been synthesised by the prenylation of 1,4-naphthoquinone (V) (for I and II), 2-methyl-1,4-naphthoquinone (VII) (for III) and 2-hydroxy-1,4-naphthoquinone (IX) (for IV) by prenyl bromide.