myristicin

1,3-benzodioxole, 4-methoxy-6-(2-propenyl)- (9CI)

CAS: 607-91-0 C11 H12 O3 MW: 192.21424000 spicy

Identification

Namemyristicin
IUPAC4-methoxy-6-prop-2-enyl-1,3-benzodioxole
CAS Number607-91-0
EINECS210-146-9
FDA UNII04PD6CT78W
Molecular FormulaC11 H12 O3
Molecular Weight192.21424000
MDL NumberMFCD00133549
Nikkaji NumberJ36.670F
Beilstein0166218
XlogP32.90 (est)

Regulatory

JECFA Food Flavoring1791 myristicin

Physical Properties

Appearance colorless clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.14300 to 1.14500 @ 25.00 °C.
Pounds per Gallon - (est). 9.511 to 9.528
Refractive Index 1.53900 to 1.54100 @ 20.00 °C.
Boiling Point 171.00 to 173.00 °C. @ 40.00 mm Hg, 95.00 to 97.00 °C. @ 0.20 mm Hg
Vapor Pressure 0.008000 mmHg @ 25.00 °C. (est)
Flash Point 194.00 °F. TCC ( 90.00 °C. )
logP (o/w) 2.586 (est)
Shelf Life 12.00 month(s) or longer if stored properly.
Storage refrigerate in tightly sealed containers.
Soluble in alcohol

Organoleptic Properties

Odor Description at 100.00 %.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-cat LDLo 400 mg/kg
Dermal Toxicitysubcutaneous-guinea pig LDLo 2000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryfragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for myristicin usage levels up to0.2000 % in the fragrance concentrate.
Recommendation for myristicin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

anise seed anise tissue culture blueberry fruit caraway plant caraway seed carrot carrot root celery celery seed coriander fruit coriander oil coriander seed crithmum maritimum l. oil turkey @ <0.10% Data cubeb oil @ trace% Data dill leaf dill oil dill root dill root oil dill seed dill shoot oil dill weed oil cuba @ 0.20% Data echinophora cinerea oil iran @ 2.20% Data fennel root oil fennel seed heracleum paphlagonicum czeczott fruit oil turkey @ 0.10% Data lovage seed mace mace oil CO2 extract @ 1.90% Data mace oil east india @ 5.92% Data nutmeg extract CO2 west indian @ 1.30% Data nutmeg flower oil @ 3.79% Data nutmeg fruit nutmeg leaf nutmeg leaf oil nutmeg leaf oil @ 0.44-1.85% Data nutmeg oil nutmeg oil hydrodistilled india @ 2.6% Data nutmeg oil india @ 9.43% Data nutmeg seed nutmeg seed oil parsley parsley fruit parsley fruit oil parsley leaf parsley leaf oil parsley leaf oil @ 8.70% Data parsley leaf oil cuba @ 63.90% Data parsley leaf oil egypt @ 8.79% Data parsley plant parsley root parsley root oil parsley seed parsley seed oil parsley seed oil @ 47.54% Data parsnip parsnip root oil pepper black pepper fruit pepper black pepper fruit oil pepper black pepper seed oil sugandha kokila berry oil @ 2.50% Data

Synonyms

5- allyl-1-methoxy-2,3-(methylene dioxy) benzene 5- allyl-1-methoxy-2,3-(methylenedioxy)benzene 5- allyl-2,3-(methylendioxy)anisole 6- allyl-4-methoxy-1,3-benzodioxole benzene, 5-allyl-1-methoxy-2,3-(methylenedioxy)- 1,3- benzodioxole, 4-methoxy-6-(2-propen-1-yl)- 1,3- benzodioxole, 4-methoxy-6-(2-propenyl)- (9CI) 4- methoxy-6-(2-propenyl)-1,3-benzodioxole 4- methoxy-6-(prop-2-en-1-yl)-1,3-benzodioxole 4- methoxy-6-prop-2-en-1-yl-1,3-benzodioxole 4- methoxy-6-prop-2-enyl-1,3-benzodioxole 4- methoxy-6-prop-2-enyl-2H-benzo[d]1,3-dioxolene PubMed: An integrated fingerprinting and kinetic approach to accelerated shelf-life testing of chemical changes in thermally treated carrot puree. PubMed: Contact toxicity and repellency of the essential oil of Liriope muscari (DECN.) bailey against three insect tobacco storage pests. PubMed: A straightforward method to determine flavouring substances in food by GC-MS. PubMed: Chemical Composition of the essential oils from Vietnamese Clausena indica and C. anisum-olens. PubMed: Cytotoxic activity against small cell lung cancer cell line and chromatographic fingerprinting of six isolated compounds from the ethanolic extract of Benjakul. PubMed: Molecular screening of insecticides with sigma glutathione S-transferases (GST) in cotton aphid Aphis gossypii using docking. PubMed: Chemical constituents and activities of the essential oil from Myristica fragrans against cigarette beetle Lasioderma serricorne. PubMed: Chemical composition and in vitro antioxidant and antibacterial activity of Heracleum transcaucasicum and Heracleum anisactis roots essential oil. PubMed: Myristicin and phenytoin toxicity in an infant. PubMed: Myristicin from nutmeg induces apoptosis via the mitochondrial pathway and down regulates genes of the DNA damage response pathways in human leukaemia K562 cells. PubMed: Parsley: a review of ethnopharmacology, phytochemistry and biological activities. PubMed: Essential oil compositions of two populations of Salvia samuelssonii growing in different biogeographical regions of Jordan. PubMed: Inhibition of Proinflammatory Cytokine Generation in Lung Inflammation by the Leaves of Perilla frutescens and Its Constituents. PubMed: Binary Combination of Carica papaya, Areca catechu and Myristica fragrans with Piperonyl Butoxide / MGK-264 against Freshwater Snail Lymnaea acuminata. PubMed: Nutmeg poisonings: a retrospective review of 10 years experience from the Illinois Poison Center, 2001-2011. PubMed: Cytotoxic activity of essential oils of aerial parts and ripe fruits of Echinophora spinosa (Apiaceae). PubMed: Chemosystematic analyses of Gingidia volatiles. PubMed: Composition and antibacterial activity of heracleum transcaucasicum and heracleum anisactis aerial parts essential oil. PubMed: GC/GC-MS analysis, isolation and identification of bioactive essential oil components from the Bhutanese medicinal plant, Pleurospermum amabile. PubMed: Effect of growth stage on essential-oil yield and composition of Daucus sahariensis. PubMed: [Chemical constituents of Conioselinum vaginatum]. PubMed: Quantitation of tr-cinnamaldehyde, safrole and myristicin in cola-flavoured soft drinks to improve the assessment of their dietary exposure. PubMed: Essential oil composition and antimicrobial activity of aerial parts and ripe fruits of Echinophora spinosa (Apiaceae) from Italy. PubMed: Forensic profiling of sassafras oils based on comprehensive two-dimensional gas chromatography. PubMed: Simple and rapid determination of myristicin in human serum. PubMed: 5-HT receptor subtypes as key targets in mediating pigment dispersion within melanophores of teleost, Oreochromis mossambicus. PubMed: Guatemalan potato moth Tecia solanivora distinguish odour profiles from qualitatively different potatoes Solanum tuberosum L. PubMed: Toxicological actions of plant-derived and anthropogenic methylenedioxyphenyl-substituted chemicals in mammals and insects. PubMed: Effects of a naturally occurring and a synthetic synergist on toxicity of three insecticides and a phytochemical to navel orangeworm (Lepidoptera: Pyralidae). PubMed: Virtual screening and in vitro assay of potential drug like inhibitors from spices against Glutathione-S-Transferase of Meloidogyne incognita. PubMed: Determination of myristicin in commonly spices applying SPE/GC. PubMed: Extraction and separation of volatile and fixed oils from seeds of Myristica fragrans by supercritical CO₂: chemical composition and cytotoxic activity on Caco-2 cancer cells. PubMed: Chemical constituents of the essential oil from aerial parts and fruit of Anisosciadium orientale. PubMed: Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents. PubMed: Aliphatic esters as targets of esterase activity in the parsnip webworm (Depressaria pastinacella). PubMed: Chemical composition and antifungal activity of essential oils and supercritical CO2 extracts of Apium nodiflorum (L.) Lag. PubMed: Chemical composition, antinociceptive and anti-inflammatory properties of essential oil from the roots of Illicium lanceolatum. PubMed: Anti-inflammatory effect of myristicin on RAW 264.7 macrophages stimulated with polyinosinic-polycytidylic acid. PubMed: Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii. PubMed: Chemical composition and antioxidant activities of the essential oil from Tornabenea bischoffii (Apiaceae). PubMed: Chemical composition of the essential oil of Pituranthos scoparius. PubMed: Polyalkoxybenzenes from plants. 5. Parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays. PubMed: 5-HT receptors as novel targets for optimizing pigmentary responses in dorsal skin melanophores of frog, Hoplobatrachus tigerinus. PubMed: Magnaporthe oryzae cell wall hydrolysate induces ROS and fungistatic VOCs in rice cell cultures. PubMed: Volatile constituents and antioxidant activity of flowers, stems and leaves of Nasturtium officinale R. Br. PubMed: A myristicin-rich essential oil from Daucus sahariensis growing in Algeria. PubMed: Optimized ultrasonic assisted extraction-dispersive liquid-liquid microextraction coupled with gas chromatography for determination of essential oil of Oliveria decumbens Vent. PubMed: Evaluation of the anxiolytic properties of myristicin, a component of nutmeg, in the male Sprague-Dawley rat. PubMed: The spice of life: an analysis of nutmeg exposures in California. PubMed: Antimicrobial and antiproliferative activity of Athamanta sicula L. (Apiaceae). PubMed: Standardization of the Unani drug - Myristica fragrans Houtt. (Javetri) - with modern analytical techniques. PubMed: Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues. PubMed: A substrate-specific cytochrome P450 monooxygenase, CYP6AB11, from the polyphagous navel orangeworm (Amyelois transitella). PubMed: Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. PubMed: [Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS]. PubMed: Genotoxic and apoptotic activities of the food flavourings myristicin and eugenol in AA8 and XRCC1 deficient EM9 cells. PubMed: Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata. PubMed: (Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor. PubMed: Anethum graveolens: An Indian traditional medicinal herb and spice. PubMed: Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. PubMed: Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning. PubMed: Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. PubMed: Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania. PubMed: Chemical composition and antimicrobial activity of Clausena indica (Dalz) Oliv. (Rutaceae) essential oil from Vietnam. PubMed: Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran. PubMed: Flower and root oils of the tunisian Daucus carota L. ssp. maritimus (Apiaceae): integrated analyses by GC, GC/MS, and 13C-NMR spectroscopy, and in vitro antibacterial activity. PubMed: Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry. PubMed: Nutmeg (Myristica fragrans Houtt.). PubMed: Essential oil composition of three Peperomia species from the Amazon, Brazil. PubMed: Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components. PubMed: Essential oil of Daucus glaber Forssk. PubMed: Chemical composition and antimicrobial activity of the essential oil from Ferula glauca L. (F. communis L. subsp. glauca) growing in Marche (central Italy). PubMed: [New neolignan from seed of Myristica fragrans]. PubMed: Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. PubMed: Perilla frutescens var. frutescens in northern Laos. PubMed: Variability in essential-oil composition of Piper marginatum sensu lato. PubMed: [GC-MS analysis of essential oil from nutmeg processed by different traditional methods]. PubMed: DNA adducts from alkoxyallylbenzene herb and spice constituents in cultured human (HepG2) cells. PubMed: Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus. PubMed: Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris. PubMed: Antioxidant activities and volatile constituents of various essential oils. PubMed: Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes. PubMed: [Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS]. PubMed: Antibacterial principles from Myristica fragrans seeds. PubMed: Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. PubMed: [Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry]. PubMed: Nutmeg intoxication in Texas, 1998-2004. PubMed: Insecticidal activity of the essential oil of Ligusticum mutellina roots. PubMed: Essential oil composition of Piper guineense and its antimicrobial activity. Another chemotype from Nigeria. PubMed: [Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation]. PubMed: Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. PubMed: Chromenes of polyketide origin from Peperomia villipetiola. PubMed: [GC-MS analysis of essential oils from seeds of Myristica fragrans in Chinese market]. PubMed: Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol. PubMed: Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson. PubMed: Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs. PubMed: Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage. PubMed: Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. PubMed: [An inaugural generalized tonic-clonic convulsive crisis following ingestion of Japanese star anise]. PubMed: Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Rutheopsis herbanica (Bolle) Hans. & Kunk., gathered in Fuerteventura (Canary Islands). PubMed: Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin. PubMed: Asaricin, the main component of Ocotea opifera Mart. essential oil. PubMed: [Effect of different processing conditions on content of myrisiticin, volatile oil and fatty lipid in semen Myristicae]. PubMed: Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre. PubMed: Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour. PubMed: Anaerobic utilization of essential oils by denitrifying bacteria. PubMed: [Comparative study on nutmeg, mace and their processed products]. PubMed: Quantitation of flavor-related alkenylbenzenes in tobacco smoke particulate by selected ion monitoring gas chromatography-mass spectrometry. PubMed: Solid phase microextraction of alkenylbenzenes and other flavor-related compounds from tobacco for analysis by selected ion monitoring gas chromatography-mass spectrometry. PubMed: Genetic analysis of nothoapiol formation in Perilla frutescens. PubMed: [Nutmeg--more than a spice]. PubMed: In vitro and in vivo metabolism of myristicin in the rat. PubMed: Preferential overexpression of a class MU glutathione S-transferase subunit in mouse liver by myristicin. PubMed: [Determination of myristicin and safrol in volatile oil of nutmeg and its processed products by HPLC]. PubMed: Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin. PubMed: Toxicological evaluation of myristicin. PubMed: A new C6-C3 compound from Cassia grandis. PubMed: Biphasic responses in synergistic interactions. PubMed: Induction of rat hepatic cytochrome P450 enzymes by myristicin. PubMed: Isolation of antifungal and larvicidal constituents of Diplolophium buchanani by centrifugal partition chromatography. PubMed: Genotoxicity of the alkenylbenzenes alpha- and beta-asarone, myristicin and elimicin as determined by the UDS assay in cultured rat hepatocytes. PubMed: Structure-genotoxicity relationships of allylbenzenes and propenylbenzenes: a quantum chemical study. PubMed: Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. PubMed: Flavor constituents in cola drinks induce hepatic DNA adducts in adult and fetal mice. PubMed: Inhibition of benzo[a]pyrene-induced tumorigenesis by myristicin, a volatile aroma constituent of parsley leaf oil. PubMed: [Determination of myristicin and safrol in the volatile oil of semen Myristicae and its processed products by TLC-scanning]. PubMed: [Effects of processing on volatile oil constituents in nutmeg and on the contents of myristicin]. PubMed: [Effects of processing methods on the amounts of volatile oil of nutmeg and on isolation and characterization of the volatile oil constituents]. PubMed: Determination of Final Steps in Biosyntheses of Essential Oil Components in Perilla frutescens. PubMed: Antiinflammatory effect of mace, aril of Myristica fragrans Houtt., and its active principles. PubMed: Decreased sensitivity of mixed-function oxidases frompapilio polyxenes to inhibitors in host plants. PubMed: Myristicin, safrole, and fagaramide as phytosynergists of xanthotoxin. PubMed: [Experimental methodology on pharmacological studies on crude drugs]. PubMed: [Chemical constituents of essential oil from Xinjiang gaoben (the rhizome of Conioselium tataricum Hoffm.) by GC-MS analysis]. PubMed: [Comparison of chemical constituents of essential oils from four species of gaoben (Ligusticum) by GC-MS analysis]. PubMed: Determination of safrole and myristicin in nutmeg and mace by high-performance liquid chromatography. PubMed: Synergism between myristicin and xanthotoxin, a naturally cooccurring plant toxicant. PubMed: 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice. PubMed: 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice. PubMed: Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. PubMed: The pharmacological effects of the ligroin extract of nutmeg (Myristica fragrans). PubMed: Toxic encounters of the dangerous kind. The nutmeg connection. PubMed: Variation of myristicin content in cultivated parsnip roots (Pastinaca sativa ssp. sativa var. hortensis). PubMed: High-pressure liquid chromatographic separation of the naturally occurring toxicants myristicin, related aromatic ethers and falcarinol. PubMed: Analysis of myristicin and falcarinol in carrots by high-pressure liquid chromatography. PubMed: Screening hallucinogenic drugs: systematic study of three behavioral tests. PubMed: Urinary excretion of tertiary amino methoxy methylenedioxy propiophenones as metabolites of myristicin in the rat and guinea pig. PubMed: The pharmacology of myristicin and nutmeg. PubMed: Possible implication of myristicin as a psychotropic substance. PubMed: Myristicin in cigarette smoke. PubMed: Evidence of monoamine oxidase inhibition by myristicin and nutmeg. PubMed: The pharmacology of myristicin. A contribution to the psychopharmacology of nutmeg. PubMed: [Evaluation of fruit and root Petroselinum on the basis of colorimetric determination of apiol and myristicin]. PubMed: The synthesis of myristicin.