HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
6-Allyl-4-methoxy-1,3-benzodioxol
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- · Myristicine · MYRISTICIN · MYRISTICIN(SG) · Myristicine-RM · 5-methoxysafrole · MYRISTICIN WITH GC · Myristicin USP/EP/BP
Identifikatoren & physikalische Daten
| CAS No. | 607-91-0 |
|---|---|
| Summenformel | C11H12O3 |
| Durchschnittliche Molmasse | 192,21 g/mol |
| Monoisotopische Masse | 192,07864424 g/mol |
| SMILES | C=CCc1cc(OC)c2c(c1)OCO2 |
| InChIKey | BNWJOHGLIBDBOB-UHFFFAOYSA-N |
| PubChem CID | 4276 |
| ChEMBL | CHEMBL481044 |
| ChEBI | CHEBI:68234 |
| EC No. | 210-146-9 |
| DTXSID | DTXSID1025693 |
| Lokaler Name | 6-Allyl-4-methoxy-1,3-benzodioxol |
Chemische & physikalische Eigenschaften
| XLogP | 2,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 27,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 205 |
| Stoffklassen | Biological Agents -> Plant Toxins |
| SpringerMaterials Properties | Boiling point |
| Dichte | 1.1416 at 20 °C g/cu cm1.143-1.145d2020 1.1437 |
| Löslichkeit | Insoluble in water, slightly soluble in ethanol, soluble in ether and benzene.Practically insoluble to insoluble in waterSoluble (in ethanol)Soluble in acetone, ethanol and methanolinsoluble in water |
| Siedepunkt | 276.5 °C171.00 to 173.00 °C. @ 40.00 mm Hg250 °Cbp40 173° |
| Schmelzpunkt | <-20 °C< -20 °C-20℃ |
| Dampfdruck | 0.00646 [mmHg] |
| Brechungsindex | Index of refraction = 1.5403 at 20 °C/D1.539-1.541nD20 1.54032 |
| Physical Description | Colorless liquid[Merck Index]Colourless oilWarm balsamic-woody aroma |
| Collision Cross Section | 141.69 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]140.8 Ų [M+H]+ |
| Other Experimental Properties | 0.183 kPa at 100 °C (1.3725 mm Hg) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | oil |
| Farbe | clear, light yellow |
| Geruch | at 100.00 %. spicy warm balsamic woody |
| Geruchsart | spicy |
| BRN | 166218 |
| Henry-Konstante | 1.8×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Light Sensitive |
| Hauptanwendungen | food and beverages |
| InChI | 1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3 |
| InChIKey | BNWJOHGLIBDBOB-UHFFFAOYSA-N |
| SMILES | COc1cc(CC=C)cc2OCOc12 |
| LogP (Verteilungskoeffizient) | 2.586 (est) |
| CAS Datenbank | 607-91-0(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-(607-91-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 90.3% (130 of 144) of all reports.Not ClassifiedAggregated GHS information provided per 144 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Gefahrenübersicht | Emergency treatment: Plants- nutmeg[HSDB] Toxicity occurs after ingestion of 1-3 whole nuts or 1-2 tablespoons of ground nutmegCNS symptoms predominate and may resemble the anticholinergic syndrome with flushing, dryness, tachycardia, hypertension, and delirium with resolution usually within 24 hoursHigher 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 irritantTargets nerves[Sigma MSDS] |
| Hazard Classes and Categories | Not Classified |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Wechselwirkungen | 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. |
| Gesundheitliche Auswirkungen | Myristicin has neurotoxic effects and hallucinogenic properties. (L1271) |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Expositionspfade | Oral (ingestion) (L1817)dermal (L1817) |
| Toxizitätsübersicht | Myristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase. (L1271) |
| Average Daily Intake | /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... |
| Signs and Symptoms | Myristicin produces a semi-conscious state, and may also cause euphoria, bloodshot eyes, and memory disturbances. It is also known to induce psychoactive effects such as visual distortions. (L1271) |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | 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). |
| Human Toxicity Excerpts | /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. |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 1 |
| UN-Transportnummer | UN 3082 9/PG 3 |
| RTECS-Nr. | CY2625000 |
| R-Sätze (R) | 52/53 |
| Toxizität | A naturally occurring methylenedioxyphenyl compound found in nutmeg. It has been suggested that myristicin may be responsible, in whole or in part, for the toxicity of nutmeg. The spice (5-15 g) causes symptoms similar to atropine poisoning: flushing of the skin, tachycardia, absence of salivation, and excitation of the CNS. Euphoria and hallucinations have given rise to abuse of this material. As a methylenedioxyphenyl compound, myristicin gives rise to a type III spectrum with reduced cytochrome P450 and can inhibit monooxygenations catalyzed by this cytochrome. |
| Sicherheitshinweise (S) | 61 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 607-91-0(Hazardous Substances Data) |
| Gefahrenklasse | Aquatic Chronic 3Repr. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Myristicin is an alkenylbenzene present in small amounts in the essential oil of nutmeg that is reported to act as a serotonin receptor antagonist, a weak monamine oxidase inhibitor, and to produce hallucinogenic effects. Abuse of myristicin has led to fatal poisoning, which has prompted improved methods for HPLC determination of myristicin in human plasma. This product is intended for forensic and research purposes.
Verwenden
A naturally occurring insecticide and acaricide with possible neurotoxic effects on neuroblastoma cells