607-91-0

Hazards Identification

Pictogram(s):

GHS Hazard Statements:

H411 (15.38%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
H412 (84.62%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P273, P391, and P501

ECHA C&L Notifications Summary:

Aggregated GHS information provided by 91 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Reported as not meeting GHS hazard criteria by 78 of 91 companies. For more detailed information, please visit ECHA C&L website.
Of the 3 notification(s) provided by 13 of 91 companies with hazard statement code(s).
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Hazard Classes and Categories:

Aquatic Chronic 2 (15.38%)
Aquatic Chronic 3 (84.62%)

Hazards Summary:

Emergency treatment: Plants- nutmeg; [HSDB] Toxicity occurs after ingestion of 1-3 whole nuts or 1-2 tablespoons of ground nutmeg; CNS symptoms predominate and may resemble the anticholinergic syndrome with flushing, dryness, tachycardia, hypertension, and delirium with resolution usually within 24 hours; Higher doses cause coma, and one fatal case has been reported; [Goldfrank, p. 626] Effects in high-dose animal studies include general anesthesia and fatty liver degeneration; [RTECS] An irritant; Targets nerves; [Sigma MSDS]

Usage

Uses

Used in Insecticides and Acaricides:
Myristicin is utilized as a naturally occurring insecticide and acaricide, capitalizing on its neurotoxic effects on various pests.
Used in Pharmaceutical Research:
As a serotonin receptor antagonist and a weak monamine oxidase inhibitor, myristicin is employed in pharmaceutical research for the development of potential treatments for various conditions related to serotonin and monoamine oxidase activity.
Used in Forensic Analysis:
Myristicin is used as a forensic tool for the detection and quantification of the substance in human plasma, aiding in investigations involving cases of abuse or fatal poisoning.
Used in Hallucinogenic Research:
Due to its hallucinogenic properties, myristicin is also used in research aimed at understanding the effects of hallucinogens on the human brain and their potential therapeutic applications.

InChI:InChI=1/C11H14O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h5-6H,3-4,7H2,1-2H3

Synthetic route

diiodomethane (75-11-6) + 5-Hydroxyeugenol (4055-72-5) → myristicin (607-91-0)

Conditions	Yield
With potassium carbonate

5-Hydroxyeugenol (4055-72-5) + 1,2-dibromomethane (74-95-3) → myristicin (607-91-0)

Conditions	Yield
With potassium carbonate
With potassium carbonate In acetone for 20h; Reflux;

diiodomethane (75-11-6) + 5-Hydroxyeugenol (4055-72-5) + acetone (67-64-1) + K2CO3 → myristicin (607-91-0)

Conditions	Yield
unter Wasserstoff;

4-allylguaiacol (97-53-0) → myristicin (607-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 2: alkaline aqueous H2O2 3: potassium carbonate View Scheme
Multi-step reaction with 3 steps 2: alkaline aqueous H2O2 3: potassium carbonate 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 / 20 h / Reflux View Scheme

5-allyl-2-hydroxy-3-methoxybenzaldehyde (22934-51-6) → myristicin (607-91-0)

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

2-allyloxy-3-methoxy-phenol (71186-63-5) → myristicin (607-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 170 - 200 °C / unter Wasserstoff 2: potassium carbonate View Scheme
Multi-step reaction with 2 steps 1: 170 - 200 °C / unter Wasserstoff 2: potassium carbonate View Scheme

2-(allyloxy)-6-methoxyphenol (51066-05-8) → myristicin (607-91-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 170 - 200 °C / unter Wasserstoff 2: potassium carbonate View Scheme
Multi-step reaction with 2 steps 1: 170 - 200 °C / unter Wasserstoff 2: potassium carbonate View Scheme

myristicin (607-91-0) → 2-bromo-1-(3-methoxy-4,5-methylenedioxyphenyl)propane (157426-98-7)

Conditions	Yield
With hydrogen bromide at 20℃;	99.22%

myristicin (607-91-0) → 4-methoxy-6-propyl-benzo[1,3]dioxole (52811-28-6)

Conditions	Yield
With 1% Pd on activated carbon; hydrogen In water at 20℃; under 760.051 Torr; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;	99%
With ethanol; palladium Hydrogenation;
With hydrogen In methanol at 20℃; under 15001.5 Torr; for 2h; Autoclave;

myristicin (607-91-0) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → ethyl 5-(3-methoxy-4,5-methylenedioxybenzyl)-4,5-dihydroisoxazole-3-carboxylate (924859-11-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	69%

myristicin (607-91-0) + N-hydroxy-4-methoxy-benzenecarboximidoyl chloride (38435-51-7) → 5-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-(4-methoxyphen-yl)-4,5-dihydroisoxazole (936080-17-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 17h;	68%
With triethylamine In dichloromethane for 24h;	67%

myristicin (607-91-0) + 4-nitrobenzonitrile (619-72-7) → 4-methoxy-7-methyl-9-(4-nitrophenyl)-6,7-dihydro-2H-[1,3]dioxolo[4,5-h]isoquinoline + 4-methoxy-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinoline

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 0.25h; Reflux;	A 20% B 55%

myristicin (607-91-0) + 4-bromobenzenecarbonitrile (623-00-7) → 9-(4-bromophenyl)-4-methoxy-7-methyl-6,7-dihydro-2H-[1,3]dioxolo[4,5-h]isoquinoline + 5-(4-bromophenyl)-4-methoxy-7-methyl-7,8-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinoline

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 0.25h; Reflux;	A 10% B 54%

myristicin (607-91-0) → 3-(3-methoxy-4,5-methylenedioxy-phenyl)-2-propen-1-ol (76897-04-6)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water at 85℃; for 0.0833333h;	24%

myristicin (607-91-0) → MMDA (13674-05-0)

Conditions	Yield
With ammonium hydroxide; Spirulina platensis phenylalanine ammonia-lyase In acetone at 37℃; for 1h; pH=8; Reagent/catalyst; Enzymatic reaction;	15.3%

methyl thiocyanate (556-64-9) + myristicin (607-91-0) → 4-methoxy-7-methyl-5-methylsulfanyl-7,8-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinoline + 4-mMethoxy-7-methyl-9-methylsulfanyl-6,7-dihydro-2H-[1,3]dioxolo[4,5-h]isoquinoline

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 0.25h; Reflux;	A 10% B 2%

methyl magnesium iodide (917-64-6) + myristicin (607-91-0) → 2-ethoxy-4-allyl-6-methoxy-phenol

Conditions	Yield
With benzene

myristicin (607-91-0) + Nitrosobenzene (586-96-9) → 3-(7-methoxy-benzo[1,3]dioxol-5-yl)-acrylaldehyde-(N-phenyl oxime )

Conditions	Yield
With diethyl ether im Dunkeln;

myristicin (607-91-0) → trans-isomyristicin (18312-21-5)

Conditions	Yield
With potassium hydroxide
With sodium under 10 Torr; beim Destillieren;

myristicin (607-91-0) → 5-methoxy-3,4-methylenedioxybenzoic acid (526-34-1)

Conditions	Yield
With potassium permanganate; water
Multi-step reaction with 3 steps 1.1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C 2.1: pyridine; ozone / methanol; chloroform / -15 - 0 °C 3.1: ammonium hydroxide; iodine / tetrahydrofuran; water / 16 h / 20 °C 3.2: 4 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C 2: pyridine; ozone / methanol; chloroform / -15 - 0 °C 3: urea hydrogen peroxide adduct; sodium hydroxide / methanol; water / Reflux View Scheme
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C / Neat (no solvent) 2: pyridine; ozone / methanol; chloroform / -15 °C 3: urea hydrogen peroxide adduct; sodium hydroxide / methanol; water / 1.5 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / 0.67 h / 100 °C 2: ozone; pyridine / methanol; chloroform / -15 °C 3: urea hydrogen peroxide adduct / methanol / 1.5 h / Reflux View Scheme

myristicin (607-91-0) → 5-methoxy-3,4-methylenedioxybenzoic acid (526-34-1) + (7-methoxy-benzo[1,3]dioxol-5-yl)-acetic acid (4408-61-1)

Conditions	Yield
With potassium permanganate; ethanol; sodium sulfate Reagens 4: Magnesiumcarbonat;

myristicin (607-91-0) → 2′,3′-dihydroxymyristicin (54306-09-1, 140385-38-2)

Conditions	Yield
With potassium hydroxide; potassium permanganate

myristicin (607-91-0) → 1-iodo-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-propan-2-ol

Conditions	Yield
With ethanol; iodine; mercury(II) oxide

myristicin (607-91-0) → (7-methoxy-benzo[1,3]dioxol-5-yl)-acetaldehyde oxime

Conditions	Yield
With palladium on activated charcoal; Lindlar's catalyst; ozone; ethyl acetate at -12℃; Erwaermen des Reaktionsprodukts mit Methanol, Hydroxylamin-hydrochlorid und wss. Kalilauge;

myristicin (607-91-0) → 4,6-dibromo-5-(2,3-dibromo-propyl)-7-methoxy-benzo[1,3]dioxole (52811-29-7)

Conditions	Yield
With bromine; acetic acid at 0℃;

myristicin (607-91-0) → myristicin nitrosite

Conditions	Yield
With cis-nitrous acid

myristicin (607-91-0) + N-methyl-N-phenylformamide (93-61-8) → 4-Methoxy-7,8-dihydronaphtho<2,3-d>-1,3-dioxol-6-carbaldehyd

Conditions	Yield
With trichlorophosphate 1) chlorobenzene, 2 h, 0 deg C, 2) chlorobenzene, 80 h, r.t.; Yield given. Multistep reaction;

myristicin (607-91-0) → trans-isomyristicin (18312-21-5) + (Z)-4-methoxy-6-(prop-2-enyl)benzo[d][1,3]dioxole

Conditions	Yield
With potassium hydroxide In ethanol for 15h; Heating; Yield given. Yields of byproduct given;
With potassium hydroxide In ethanol for 15h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

myristicin (607-91-0) + ethanol (64-17-5) + iodine (7553-56-2) + yellow mercury oxide → 13-iodo-12-oxy-3-methoxy-4.5-methylenedioxy-1-propyl-benzene

myristicin (607-91-0) + mercury(II) diacetate (1600-27-7) + water (7732-18-5) + benzene (71-43-2) → 1-hydroxymethyl-2-<7-methoxy-benzo<1,3>dioxol-5-yl>-ethylmercury acetate

myristicin (607-91-0) + diethyl ether (60-29-7) + Nitrosobenzene (586-96-9) → 3-methoxy-4.5-methylenedioxy-cinnamaldoxime-N-phenyl ether

myristicin (607-91-0) + bromine (7726-95-6) + acetic acid (64-19-7) → bz-dibromo-myristicin dibromide

Conditions	Yield
at 0℃;

myristicin (607-91-0) + alcoholic KOH-solution → isomyristicin

Upstream product

• 75-11-6 diiodomethane 
• 4055-72-5 5-Hydroxyeugenol 
• 74-95-3 1,1-dibromomethane 
• 67-64-1 acetone 
• 22934-51-6 5-allyl-2-hydroxy-3-methoxybenzaldehyde 
• 71186-63-5 2-allyloxy-3-methoxy-phenol 
• 51066-05-8 2-(allyloxy)-6-methoxyphenol 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 52811-28-6 4-methoxy-6-propyl-benzo[1,3]dioxole 
• 18312-21-5 trans-isomyristicin 
• 526-34-1 5-methoxy-3,4-methylenedioxybenzoic acid 
• 4408-61-1 (7-methoxy-benzo[1,3]dioxol-5-yl)-acetic acid 
• 23693-38-1 β-(3-methoxy-4,5-methylenedioxy)phenylethylamine 
• 936080-17-0 5-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-(4-methoxyphen-yl)-4,5-dihydroisoxazole 
• 1370046-04-0 C₂₀H₂₃NO₆ 
• 1370045-99-0 C₂₀H₂₃NO₆ 
• 22934-59-4 (7-methoxybenzo[d][1,3]dioxol-5-yl)methanol 
• 1240140-17-3 2-(4-methoxyphenyl)-3-oxo-3-(3-methoxy-4,5-methylenedioxyphenyl)propanenitrile 
• 1276358-64-5 3-(4-methoxyphenyl)-3-oxo-2-(3-methoxy-4,5-methylenedioxyphenyl)propanenitrile 
• 1301751-69-8 4-(4-methoxyphenyl)-5-(3-methoxy-4,5-methylenedioxyphenyl)-1H-pyrazol-3-amine 
• 1301751-70-1 5-(4-methoxyphenyl)-4-(3-methoxy-4,5-methylenedioxyphenyl)-1H-pyrazol-3-amine 
• 24203-70-1 6,7,3'-trimethoxy-4',5'-methylenedioxyisoflavone 

Relevant academic research and scientific papers

SYNTHESIS OF ELEMICIN AND TOPICAL ANALGESIC COMPOSITIONS

The present invention is directed to the synthesis of elemicin and its isomeric form, and their use in topical analgesic formulations, including for dental and veterinary use. Various compositions include gels, films, dressings, cavity filling gels, having analgesic and/or antifungal properties.

Method of causing the reduction of physiological and/or subjective reactivity to stress in humans being subjected to stress conditions

Described is a method for reducing physiological and/or subjective reactivity to stress in humans being subjected to stress conditions. The method consists of administering to such humans an effective amount of a physiological and/or subjective stress reactivity-reducing substance selected from the group consisting of: (i) Nutmeg Oil; (ii) Mace Extract; (iii) Neroli Oil; (iv) Valerian Oil; (v) Myristicin; (vi) Isoelemicin; and (vii) Elemicin. Administration is through inhalation or transdermally using one or more of the above ingredients alone or in a suitable composition such as ethanol and/or a perfume composition, cologne or perfumed article (e.g., air freshener or deodorant stick). Also described is a method for detecting the reduction of physiological and/or subjective reactivity to stress in a human.