6-Allyl-4-methoxy-1,3-benzodioxol

1.1416 at 20 °C g/cu cm

1.143-1.145

Insoluble in water, slightly soluble in ethanol, soluble in ether and benzene.

Practically insoluble to insoluble in water

Soluble (in ethanol)

276.5 °C

171.00 to 173.00 °C. @ 40.00 mm Hg

250 °C

<-20 °C

< -20 °C

Index of refraction = 1.5403 at 20 °C/D

1.539-1.541

Colorless liquid; [Merck Index]

Liquid

Colourless oil; Warm balsamic-woody aroma

141.69 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

140.8 Ų [M+H]+

This chemical does not meet GHS hazard criteria for 90.3% (130 of 144) of all reports.

Not Classified

Aggregated GHS information provided per 144 reports by companies from 5 notifications to the ECHA C&L Inventory.

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]

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Simultaneous topical application of myristicin followed by paraoxon application, caused substantial incr in the toxicity of paraoxon. LD50 values indicated a 10-fold incr in paraoxon toxicity due to a topical application of myristicin at a sublethal dosage of 2 ug/fly.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a structure estimation method(2), indicates that myristicin is expected to have low mobility in soil(SRC). Volatilization of myristicin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Myristicin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.5X10-3 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a structure estimation method(2), indicates that myristicin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.4X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 100(SRC), from an estimated log Kow of 3.53(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myristicin, which has an estimated vapor pressure of 6.5X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase myristicin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.3X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Analysis of water-distilled Sri Lankan nutmeg oil and steam-distilled Indonesian nutmeg oil revealed 3.3 and 5.5% myristicin, respectively(1). Myristicin was identified as a major volatile odor compound released from full-fat and reduced-fat frankfurters(2).

/SCOGS/ calculations ... indicate that the intake level of nutmeg oil and its equivalent in the form of nutmeg and mace, based on the total imports available annually for use in food in the U.S., is of the order of 0.05 mg per kg per day for adults. Assuming a maximum content of 6 percent safrole in the oil, possible daily intake of safrole would be about 4 mcg per kg per day for an adult and about 5 times this amount for a child 6-11 months of age, who, according to the NRC survey, consumes the largest amounts of nutmeg products per kg of body weight. If myristicin is capable of conversion to safrole in vivo, intakes could be about double these amounts. All of these intake estimates would be low, of course, for any in the population who are particularly heavy consumers of food products containing nutmeg...

Using a structure estimation method based on molecular connectivity indices(1), the Koc of myristicin can be estimated to be 950(SRC). According to a classification scheme(2), this estimated Koc value suggests that myristicin is expected to have low mobility in soil(SRC).

Myristicin is a naturally occurring benzodioxole compound found in anise, Star anise, black pepper, carrot, common fennel, mace, nutmeg, sweet fennel, many natural oils, and flavoring agents.

Myristicin is found in nutmeg, mace, and carrots(1).

/SIGNS AND SYMPTOMS/ Ingestion of five or more grams of nutmeg causes acute nutmeg poisoning, which includes giddiness, hallucinations, and feelings of depersonalization. Symptoms usually appear three to six hours after ingestion of 1-3 whole nutmegs or 5-15 gm of the grated spice. Recovery usually occurs within 24 hours. Nevertheless, duration of action may extend beyond several days and even include death. /Nutmeg/

/SIGNS AND SYMPTOMS/ Chronic poisoning by oral administration has caused temporary (up to six months) psychosis in prison inmates. /Myristica fragrans/

/SIGNS AND SYMPTOMS/ Myristicin, or methoxysafrole, is the principal aromatic constituent of the volatile oil of nutmeg, the dried ripe seed of Myristica fragrans. Myristicin is also found in several members of the carrot family (Umbelliferae). Several intoxications have been reported after an ingestion of approximately 5 g of nutmeg, corresponding to 1-2 mg myristicin/kg body weight (b.w.). Although these intoxications may be ascribed to the actions of myristicin, it is likely that other components of nutmeg may also be involved. ...

/SIGNS AND SYMPTOMS/ The effects by inhalation are generally similar to those experienced via oral administration with the exception that onset is faster by 15 minutes. /Myristica fragrans/

For more Human Toxicity Excerpts (Complete) data for MYRISTICIN (11 total), please visit the HSDB record page.

To evaluate the hepatoprotective activity of spices, 21 different spices were fed to rats with liver damage caused by lipopolysaccharide (LPS) plus d-galactosamine (D-GalN). As assessed by plasma aminotranferase activities, nutmeg showed the most potent hepatoprotective activity. Bioassay-guided isolation of the active compound from nutmeg was carried out in mice by a single oral administration of the respective fractions. Myristicin, one of the major essential oils of nutmeg, was found to possess extraordinarily potent hepatoprotective activity. Myristicin markedly suppressed LPS/D-GalN-induced enhancement of serum TNF-alpha concentrations and hepatic DNA fragmentation in mice. These findings suggest that the hepatoprotective activity of myristicin might be, at least in part, due to the inhibition of TNF-alpha release from macrophages. ...

Mouse hepatoma Hepa-1c1c7 (Hepa-1) cells were treated with myristicin to assess the role of myristicin in the process of Cyp1a-1 induction. Treatment of Hepa-1 cells with myristicin increased Cyp1a-1 transcription in a dose-dependent manner as shown by analysis of 7-ethoxyresorufin O-deethylase activity, Cyp1a-1 protein level, and Cyp1a-1 mRNA. Myristicin, however, did not competitively displace [3H]2,3,7,8-tetrachlorodibenzo-p-dioxin from the Hepa-1 cytosolic aryl hydrocarbon (Ah) receptor in a competitive Ah receptor binding analysis using sucrose density gradient sedimentation and did not affect formation of DNA-protein complexes between the Ah receptor and its DRE target in a gel mobility shift assay using oligonucleotides corresponding to DRE 3 of the Cyp1a-1. ...

In mice, the major metabolic pathway for ... myristicin includes cleavage of the methylenedioxyphenol residue and exhalation of the methylene carbon atom as carbon dioxide.

Myristicin yields 3-methoxycatechol probably in mouse, housefly; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-piperidyl-1-propanone in rat, guinea pig; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-pyrrolidinyl-1-propanone in rat, guinea pig. /From table/

Myristicin was converted into 3-methoxy-4,5-methylenedioxyamphetamine during perfusion of isolated rat liver or incubation with rat liver homogenates.

2 N-containing metabolites of myristicin were excreted in the urine of rats and guinea pigs following oral or ip admin. In the rats the metabolite was 3-piperidyl-1,3-methoxy-4,5-mehtylenedioxyphenyl)-1-propanone while the major metabolite in the guinea pig was 3-pyrrolidinyl-1(3-methoxy-4,5-methylenedioxy-phenyl)-1-propanone.

For more Metabolism/Metabolites (Complete) data for MYRISTICIN (8 total), please visit the HSDB record page.

Myristicin has known human metabolites that include 5-allyl-1-methoxy-2,3-dihydroxybenzene.

An aromatic ether found in nutmeg, parsley, and carrots; [Merck Index] Thought to be the main active ingredient in nutmeg; [Goldfrank, p. 626]

Myristicin [5-allyl-1-methoxy-2,3-(methylenedioxy)benzene] is a flavoring plant constituent and has been known to produce significant psychopharmacological responses as well as insecticidal activity.

Myristicin is a plant toxin found in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. It is a naturally occurring insecticide and acaricide. (L1271)

... it is to be recognized that as much as 6 percent of safrole, a weak hepatocarcinogen, is reported to be present in the essential oil of East Indian nutmeg, the major U.S. source. In 1960 FDA prohibited the use of safrole in food. Moreover, the closely related methoxy derivative of safrole, myristicin, is also present in some nutmeg oils in amounts approximating 5 percent.

THE AROMATIC FRACTION OF OIL OF NUTMEG, OBTAINED FROM 20 G OF NUTMEG, WAS REPORTED TO CONSIST OF: MYRISTICIN 210 MG; ELEMICIN 2 MG; EUGENOL 5 MG; ISOEUGENOL 6 MG; METHYLEUGENOL 18 MG; METHYLISOEUGENOL 11 MG; METHOXYEUGENOL 8 MG. NUTMEGS USUALLY CONTAIN FROM 5 TO 15% VOLATILE OIL, DEPENDING UPON GEOGRAPHIC ORIGIN AND LENGTH OF STORAGE.

Myristicin, 1-allyl-3,4-methylenedioxy-5-methoxybenzene, is a naturally occurring alkenylbenzene compound found in the nutmeg.