Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2019-11-26 03:10:33 UTC
Primary IDFDB014654
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMyristicin
DescriptionConstituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase. Myristicin is found in many foods, some of which are parsley, pepper (spice), wild carrot, and highbush blueberry.
CAS Number607-91-0
Structure
Thumb
Synonyms
SynonymSource
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzeneMeSH
AsaricinMeSH
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9ci)HMDB
1-Allyl-3-methoxy-4,5-methylenedioxybenzeneHMDB
1-Methoxy-2,3-methylenedioxy-5-(2-propenyl)benzeneHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxoleHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9ciHMDB
4-Methoxy-6-[2-propenyl]-1,3-benzodioxoleHMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)-benzeneHMDB
5-Allyl-2,3-(methylendioxy)anisoleHMDB
6-Allyl-4-methoxy-1,3-benzodioxoleHMDB
Myristicin (6ci)HMDB
Myristicin from parsley leaf oilHMDB
MyristicineHMDB
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-biospider
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9CI)biospider
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9CIdb_source
Benzene, 5-allyl-1-methoxy-2,3-(methylenedioxy)-biospider
Myristicin (6CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP2.47ALOGPS
logP2.54ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.58 m³·mol⁻¹ChemAxon
Polarizability20.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12O3
IUPAC name4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
InChI IdentifierInChI=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
InChI KeyBNWJOHGLIBDBOB-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC=C)=CC2=C1OCO2
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
Classification
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 68.74%; H 6.29%; O 24.97%DFC
Melting Point<-20 oC
Boiling PointBp0.2 95-97°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2020 1.14DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-371b2263b19500bf8f812014-09-20View Spectrum
Predicted GC-MSMyristicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fr-1900000000-f2a18c6e6e42ac39f661Spectrum
Predicted GC-MSMyristicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-0api-2900000000-351fe6c26efba614a8812017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ac75cb6f6c3586da7aea2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-b85689ec228e938e0ecc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-5900000000-b81250e22454ed5d59d32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3477a22f9a26a9c1d3892015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-d7d0d133097da9fb4ec32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-4900000000-223806e9de1823c5a6e22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-f50d22f4768250e3bdf72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-eccd8c2af56eaae25cc62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fu-9300000000-7be3c7d384d05c36876b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3b8fc77e2c5dffca77652021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-bdb133e54a9aea38147a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-7900000000-cea14d0b0dcb3a57c3522021-09-25View Spectrum
NMR
TypeDescriptionView
ChemSpider ID4125
ChEMBL IDCHEMBL481044
KEGG Compound IDC10480
Pubchem Compound ID4276
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35873
CRC / DFC (Dictionary of Food Compounds) IDJTL34-L:JTL34-L
EAFUS IDNot Available
Dr. Duke IDMYRISTICIN
BIGG IDNot Available
KNApSAcK IDC00002762
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID607-91-0
GoodScent IDrw1104961
SuperScent IDNot Available
Wikipedia IDMyristicin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
AmphetaminagenicAn agent that stimulates the release of dopamine and norepinephrine, increasing alertness and energy. Therapeutically, it is used to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity, by enhancing focus, reducing fatigue, and suppressing appetite.DUKE
AnestheticA drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti depressant52217 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-stress52217 An agent that reduces stress symptoms, commonly used in managing anxiety disorders, promoting relaxation, and mitigating the biological effects of stress on the body, such as hypertension and immune suppression, with therapeutic applications in mental health and key medical uses in cardiology and neurology.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HallucinogenicAn agent that alters perception, thought, and mood, causing hallucinations and subjective changes. It has a biological role in serotonin receptor modulation. Therapeutically, it's explored for treating mental health disorders, such as depression and anxiety. Key medical uses include research in psychiatric treatment and potential applications in palliative care.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
HypnoticAn agent that induces sleep, used to treat insomnia and facilitate surgical anesthesia, playing a key role in regulating sleep patterns and providing therapeutic relief for sleep disorders.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
Monoamine-oxidase inhibitor23924 An agent that blocks monoamine oxidase enzymes, increasing neurotransmitter levels. Therapeutically, it reduces depression symptoms and is commonly used in managing depression, anxiety disorders, and Parkinson's disease.DUKE
Neurotoxic50910 A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.DUKE
Oxytocic36063 A hormone that stimulates uterine contractions, playing a key role in childbirth and lactation. Therapeutically, it induces labor, controls postpartum bleeding, and promotes milk letdown. Medical uses include augmenting labor, treating postpartum hemorrhage, and assisting with breastfeeding.DUKE
ParalyticAn agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Psychoactive35471 A substance that affects brain function, altering mood, perception, or consciousness. It plays a biological role in modifying neurotransmitter activity. Therapeutically, psychoactive substances have applications in managing mental health disorders, such as depression and anxiety. Key medical uses include treating psychiatric conditions, including attention deficit hyperactivity disorder (ADHD), and certain sleep disorders.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
Serotoninergic48278 An agent that modulates serotonin activity, regulating mood, appetite, and sleep. It has therapeutic applications in treating depression, anxiety, and mood disorders, with key medical uses including antidepressants, anxiolytics, and anti-migraine medications.DUKE
Tachycardic38070 An agent that increases heart rate, playing a biological role in stress response and exercise. Therapeutically, it is used to manage bradycardia (abnormally slow heart rate) and cardiac arrest. Key medical uses include treating symptomatic bradycardia, Adams-Stokes syndrome, and asystole, helping to restore normal heart rhythm and maintain adequate blood circulation.DUKE
Utero tonic52217 An agent that stimulates and strengthens the uterine muscles, aiding in childbirth and reducing postpartum bleeding. Therapeutically, it is used to induce labor, manage uterine atony, and treat menstrual disorders, promoting overall reproductive health.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.