487-11-6

Basic information

• Product Name: Elemicin
• Synonyms: 1,2,3-TRIMETHOXY-5-(2-PROPENYL)BENZENE;5-ALLYL-1,2,3-TRIMETHOXYBENZENE;ELEMICIN;1,2,3-trimethoxy-5-(2-propenyl)-benzen;1,2,3-trimethoxy-5-allylbenzene (elemicin);3,4,5-Trimethoxyallylbenzene;4-allyl-1,2,6-trimethoxybenzene;5-allyl-1,2,3-trimethoxy-benzen
• CAS NO: 487-11-6
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• EINECS: 207-649-0
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 487-11-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 279.8 °C at 760 mmHg
• Flash Point: 92.6 °C
• Appearance: /
• Density: 1.011 g/cm³
• Vapor Pressure: 0.00666mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: Elemicin(CAS DataBase Reference)
• NIST Chemistry Reference: Elemicin(487-11-6)
• EPA Substance Registry System: Elemicin(487-11-6)

Safety Data

• Hazardous Substances Data: 487-11-6(Hazardous Substances Data)

Usage

Description

Elemicin is a trioxygenated phenylpropane that has been found in A. dracunculus. It is active against S. aureus, B. subtilis, and C. albicans (MICs = 600, 2,500, and 1,000 mg/L, respectively) but not E. coli, K. pneumoniae, P. aeruginosa (MICs = >8,000 mg/L for all), or L. monocytogenes (MIC = >3,000 mg/L). Elemicin is toxic to mice following metabolic activation to 1’-hydroxyelemicin by the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. It increases plasma and hepatic triglyceride levels, decreases stearoyl-CoA desaturase 1 (Scd1) expression, and induces hepatomegaly in mice when administered at a dose of 500 mg/kg per day for three weeks.

Chemical Properties

Clear Colorless Oil

Uses

A constituent of the essential oil of nutmeg and is responsible for the psychoactive effects of nutmeg. Also a minor constituent of the oleoresin and essential oil of Manila elemi (Canarium luzonicum). Exhibits anticholinergic-like effects in humans.

InChI:InChI=1/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3

Synthetic route

4-allyl-2,6-dimethoxyphenol (6627-88-9) + methyl iodide (74-88-4) → elemicin (487-11-6)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 24h;	96%
With potassium carbonate
With potassium carbonate In acetone for 6h; Heating;

5-allyl-2,3-dimethoxyphenol + methyl iodide (74-88-4) → elemicin (487-11-6)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 16h;	95%

4-allyl-2,6-dimethoxyphenol (6627-88-9) + dimethyl sulfate (77-78-1) → elemicin (487-11-6)

Conditions	Yield
With potassium hydroxide for 4.5h;	93%
With sodium hydroxide

allyl bromide (106-95-6) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8) → elemicin (487-11-6)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 110℃; for 15h; Suzuki-Miyaura coupling; Inert atmosphere;	89%

Allyl acetate (591-87-7) + 1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → elemicin (487-11-6)

Conditions	Yield
With pyridine; nickel(II) iodide; 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine; tetrabutylammomium bromide; magnesium chloride; zinc In N,N-dimethyl acetamide at 60℃; for 12h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; regioselective reaction;	87%
With pyridine; nickel(II) iodide; tetrabutylammomium bromide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl acetamide at 60℃; for 12h; Inert atmosphere;	79%

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → elemicin (487-11-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In tetrahydrofuran at 85℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;	75%

1,2,3-trimethoxy-5-chlorobenzene (2675-80-1) + allyl-trimethyl-silane (762-72-1) → elemicin (487-11-6)

Conditions	Yield
In water; acetonitrile for 36h; Irradiation;	54%

5-Hydroxyeugenol (4055-72-5) + dimethyl sulfate (77-78-1) → elemicin (487-11-6)

Conditions	Yield
With potassium carbonate; acetone
With potassium carbonate In acetone for 6h; Reflux;

1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene (5438-54-0) + methyl iodide (74-88-4) → elemicin (487-11-6)

Conditions	Yield
(i) (heating), (ii) KOH, EtOH, (iii) /BRN= 969135/; Multistep reaction;

dimethyl sulfate (77-78-1) + sodium-<2.6-dimethoxy-4-allyl-phenolate> → elemicin (487-11-6)

Conditions	Yield
With toluene; calcium carbonate Erhitzen auf Siedetemperatur;

3,4,5-Trimethoxyaniline (24313-88-0) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / acetonitrile; H2O / 36 h / Irradiation View Scheme

1,3-dimethoxy-2-hydroxy-benzene (91-10-1) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / K2CO3 / acetone / 24 h / 20 °C 2: 92 percent / 2 h / 200 °C 3: 96 percent / K2CO3 / acetone / 24 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: K2CO3 / acetone 2: 2 h / 200 °C 3: K2CO3 View Scheme
Multi-step reaction with 3 steps 1: K2CO3; acetone 2: 220 °C 3: NaOH-solution View Scheme

1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene (5438-54-0) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / 2 h / 200 °C 2: 96 percent / K2CO3 / acetone / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 2 h / 200 °C 2: K2CO3 View Scheme
Multi-step reaction with 2 steps 1: 220 °C 2: NaOH-solution View Scheme

4-allylguaiacol (97-53-0) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: alkaline aqueous H2O2 3: K2CO3; acetone View Scheme
Multi-step reaction with 3 steps 1: hexan-1-amine / 6 h / Heating 2: dihydrogen peroxide; pyridine; sodium hydroxide / water / 1.5 h / 20 °C 3: potassium carbonate / acetone / 6 h / Reflux View Scheme

5-allyl-2-hydroxy-3-methoxybenzaldehyde (22934-51-6) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkaline aqueous H2O2 2: K2CO3; acetone View Scheme

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (214360-67-5) + 3-chloroprop-1-ene (107-05-1) → elemicin (487-11-6)

Conditions	Yield
Stage #1: 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane; 3-chloroprop-1-ene With bis(dibenzylideneacetone)-palladium(0) In methanol at 20℃; for 0.166667h; Inert atmosphere; Glovebox; Stage #2: With potassium fluoride In methanol at 20℃; for 24h; Inert atmosphere; Glovebox;	140 mg

1,2,3-trimethoxybenzene (634-36-6) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 18 h / 80 °C / Inert atmosphere; Glovebox 2.1: bis(dibenzylideneacetone)-palladium(0) / methanol / 0.17 h / 20 °C / Inert atmosphere; Glovebox 2.2: 24 h / 20 °C / Inert atmosphere; Glovebox View Scheme

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) + allyltributylstanane (24850-33-7) → elemicin (487-11-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 80℃; Stille Cross Coupling;

2,3-dimethoxyphenol (5150-42-5) → elemicin (487-11-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: [bis(acetoxy)iodo]benzene / 0 - 20 °C 2: titanium tetrachloride / toluene; dichloromethane / 0.5 h / 0 °C 3: potassium carbonate / acetonitrile / 16 h / 20 °C View Scheme

5-allyl-1,2,3-trihydroxybenzene + methyl iodide (74-88-4) → elemicin (487-11-6)

Conditions	Yield
With silver(l) oxide

elemicin (487-11-6) → isoelemicin (487-12-7, 5273-84-7, 5273-85-8)

Conditions	Yield
With nickel(II) iodide; 6,6'-dimethyl-2,2'-bipyridine; phosphonic acid diethyl ester; zinc In N,N-dimethyl acetamide at 35℃; for 24h;	97%
With (μ-Cl)2Ni2(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)2 In chlorobenzene at 20℃; for 3h;	90%
With potassium hydroxide In ethanol
With Grotjahn’s catalyst In [(2)H6]acetone at 20℃; for 0.333333h; Reagent/catalyst; Temperature; Gas phase; Inert atmosphere; diastereoselective reaction;	98 %Spectr.

elemicin (487-11-6) + C12H13NO4 → (E)-3-methyl-3-(4-nitrophenyl)-6-(3,4,5-trimethoxyphenyl)hex-5-en-2-one

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine; tert-butyl alcohol In tetrahydrofuran at 80℃; for 22h; Schlenk technique; Inert atmosphere;	90%

elemicin (487-11-6) + 1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene (69843-08-9) → 5-(6,6-difluoro-5-(4-methoxyphenyl)hex-5-en-3-yl)-1,2,3-trimethoxybenzene

Conditions	Yield
With 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide trihydrate; Triethoxysilane; tetrabutylammomium bromide; lithium fluoride; triphenylphosphine In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	86%

elemicin (487-11-6) → 3-(3',4',5'-trimethoxyphenyl)-prop-2-en-1-al (34346-90-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water Ambient temperature;	80%

elemicin (487-11-6) → C12H16O6 (1373139-34-4)

Conditions	Yield
With ozone	80%

elemicin (487-11-6) → 3,4,5-trimethoxy-benzaldehyde (86-81-7)

Conditions	Yield
With iron(III) chloride; tetramethyldisiloxane In ethanol at 20℃; for 24h;	78%
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C / Neat (no solvent) 2: pyridine; ozone / methanol; chloroform / -15 °C View Scheme
Stage #1: elemicin With tetrabutylammomium bromide; potassium hydroxide at 100℃; for 0.666667h; Stage #2: With pyridine; ozone In methanol; chloroform at -15℃;
Stage #1: elemicin With potassium hydroxide at 100℃; for 0.666667h; Stage #2: With ozone In pyridine; methanol; chloroform at 15℃;

tert.-butylhydroperoxide (75-91-2) + elemicin (487-11-6) + Langlois reagent (2926-29-6) → C17H25F3O5

Conditions	Yield
With potassium phosphate; cobalt(II) diacetate tetrahydrate In water; acetonitrile at 75℃; Schlenk technique; Inert atmosphere;	78%

elemicin (487-11-6) → 3,4,5-trimethoxycinnamaldehyde (71277-13-9, 34346-90-2, 71277-12-8) + 4,5-Dichloro-3-hydroxy-6-[(E)-3-(3,4,5-trimethoxy-phenyl)-allyloxy]-phthalonitrile + 4,5-Dichloro-3,6-bis-[(E)-3-(3,4,5-trimethoxy-phenyl)-allyloxy]-phthalonitrile

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water Ambient temperature;	A 71% B n/a C n/a

elemicin (487-11-6) → 1-(3,4,5-trimethoxyphenyl)-2-bromopropane (121637-68-1)

Conditions	Yield
With hydrogen bromide In acetic acid at 0℃; for 3h;	70%

1-methyl-2(1H)-quinoxalinone (6479-18-1) + elemicin (487-11-6) + Langlois reagent (2926-29-6) → 1-methyl-3-(4,4,4-trifluoro-1-(3,4,5-trimethoxyphenyl)-butan-2-yl)quinoxalin-2(1H)-one

Conditions	Yield
With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;	70%
With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h;	70%

elemicin (487-11-6) + Langlois reagent (2926-29-6) → 5-(2-azido-4,4,4-trifluorobutyl)-1,2,3-trimethoxybenzene

Conditions	Yield
With tert.-butylhydroperoxide; trimethylsilylazide; manganese(III) triacetate dihydrate In water; acetonitrile at 45℃; Schlenk technique; Inert atmosphere;	64%
With tert.-butylhydroperoxide; trimethylsilylazide; manganese(III) triacetate dihydrate In water; acetonitrile at 45℃; for 12h; Inert atmosphere;	64%

elemicin (487-11-6) + triethylaluminum (97-93-8) → 2-[(3,4,5-trimethoxyphenyl)methyl]butane-1,4-diol

Conditions	Yield
Stage #1: elemicin; triethylaluminum With zirconocene dichloride In toluene at 22℃; Inert atmosphere; Stage #2: With oxygen at 0℃; for 2h;	60%

elemicin (487-11-6) + α-allyl,α-methyl nitroacetone (1278455-80-3) → (E)-1,2,3-trimethoxy-5-(4-methyl-4-nitrohepta-1,6-dien-1-yl)-benzene

Conditions	Yield
With water; palladium diacetate; caesium carbonate; triphenylphosphine; tert-butyl alcohol In dichloromethane; 1,2-dichloro-ethane at 80℃; for 22h; Schlenk technique; Inert atmosphere;	57%

elemicin (487-11-6) + N-methyl-N-phenylformamide (93-61-8) → 3,4-dihydro-6,7,8-trimethoxy-2-naphthalenecarboxaldehyde (71687-96-2)

Conditions	Yield
With trichlorophosphate other methoxyallylbenzenes;	56%
With trichlorophosphate 1) 10 deg C, 45 min 2) r.t., 24 h; Yield given. Multistep reaction;
With trichlorophosphate 1) chlorobenzene, 2 h, 0 deg C, 2) chlorobenzene, 80 h, r.t.; Yield given. Multistep reaction;

elemicin (487-11-6) + benzamidine monohydrochloride (1670-14-0) → 2-phenyl-4-(3,4,5-trimethoxyphenyl)pyrimidine

Conditions	Yield
With oxygen; caesium carbonate In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 24h;	56%

elemicin (487-11-6) + aniline (62-53-3) → 2-(3,4,5-trimethoxyphenyl)quinoline

Conditions	Yield
With water; oxygen; palladium diacetate; toluene-4-sulfonic acid In dimethyl sulfoxide at 110℃; under 760.051 Torr; for 24h;	55%

elemicin (487-11-6) + 5-iodo-2-methoxytropone (343962-18-5) → C20H22O5 (1616515-30-0)

Conditions	Yield
With palladium diacetate; triphenylphosphine; silver carbonate In tetrahydrofuran Heck Reaction;	50%

elemicin (487-11-6) → 3-(3',4',5'-trimethoxyphenyl)-1,2-propanediol (54306-10-4, 140385-37-1)

Conditions	Yield
With potassium permanganate In ethanol; water for 0.05h;	20%
With potassium permanganate

elemicin (487-11-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,4-dihydro-6,7,8-trimethoxy-2-naphthalenecarboxaldehyde (71687-96-2) + 6-allyl-2,3,4-trimethoxybenzaldehyde (83923-94-8)

Conditions	Yield
With trichlorophosphate In dichloromethane for 120h; Ambient temperature;	A 17% B 16.7%

elemicin (487-11-6) + 4,4a-dihydro-1,5,5,6,9,9-hexamethoxy-3,8a-bis(2-propenyl)-1,4-ethanonaphthalene-6,10(4H)-dione (38451-63-7) → 4-allyl-2,6-dimethoxyphenol (6627-88-9) + demethylisoheterotropanone (78660-19-2, 78660-20-5) + isoheterotropanone (70280-34-1, 70287-69-3) + heterotropanone (70280-34-1, 70287-69-3)

Conditions	Yield
at 175 - 180℃; for 1.5h; Further byproducts given;	A 3% B 2% C 13% D 14%

elemicin (487-11-6) + 4,4a-dihydro-1,5,5,6,9,9-hexamethoxy-3,8a-bis(2-propenyl)-1,4-ethanonaphthalene-6,10(4H)-dione (38451-63-7) → 4-allyl-2,6-dimethoxyphenol (6627-88-9) + demethylheterotropanone (78660-19-2, 78660-20-5) + isoheterotropanone (70280-34-1, 70287-69-3) + heterotropanone (70280-34-1, 70287-69-3)

Conditions	Yield
at 175 - 180℃; for 1.5h; Further byproducts given;	A 3% B 2% C 13% D 14%

elemicin (487-11-6) → 1,3-dimethoxy-5-propylbenzene (41395-10-2)

Conditions	Yield
With ethanol; sodium

elemicin (487-11-6) → 3,4,5-trimethoxyphenylacetaldehyde (5320-31-0)

Conditions	Yield
With oxygen; ozone; ethyl acetate at -15℃; und anschliessende Hydrierung an Palladium/Calciumcarbonat unter Kuehlung; Isolierung als Natriumhydrogensulfit-Addukt;
With water; ozone; benzene
Multi-step reaction with 2 steps 1: KMnO4 2: HIO4; H2O View Scheme

Upstream product

• 77-78-1 dimethyl sulfate 
• 2675-80-1 1,2,3-trimethoxy-5-chlorobenzene 
• 762-72-1 allyl-trimethyl-silane 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 74-88-4 methyl iodide 
• 5150-42-5 2,3-dimethoxyphenol 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 24850-33-7 allyltributylstanane 
• 634-36-6 1,2,3-trimethoxybenzene 
• 214360-67-5 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane 
• 107-05-1 3-chloroprop-1-ene 
• 591-87-7 Allyl acetate 
• 106-95-6 allyl bromide 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 

Downstream Products

• 34346-90-2 3-(3',4',5'-trimethoxyphenyl)-prop-2-en-1-al 
• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 
• 5320-31-0 3,4,5-trimethoxyphenylacetaldehyde 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 118-41-2 Eudesmic acid 
• 956390-99-1 2,2-dichloro-3-(3,4,5-trimethoxybenzyl)cyclobutanone 
• 1616515-30-0 C₂₀H₂₂O₅ 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 

Relevant articles and documents

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