M9411
Myristicin from parsley leaf oil
≥85% (HPLC), oil
Synonym(s):
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole
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About This Item
Empirical Formula (Hill Notation):
C11H12O3
CAS Number:
Molecular Weight:
192.21
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥85% (HPLC)
form
oil
color
clear light yellow
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
SMILES string
COc1cc(CC=C)cc2OCOc12
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
InChI key
BNWJOHGLIBDBOB-UHFFFAOYSA-N
General description
Myristicin, a phenylpropene, is an essential oil component.[1] It has anticholinergic and psychotropic activities.[2] Myristicin blocks cytochrome P450 monooxygenases, which detoxifies furanocoumarins.[1] It functions as a serotonin receptor agonist and hallucinogenic agent.[2] Myristicin stimulates glutathione S-transferase activity and might function as a chemopreventive agent.[3] It acts as a precursor for the metabolite 3,4- methylenedioxymethamphetamine (MDMA).[4]
Application
Myristicin from parsley leaf oil has been used to study competitive and uncompetitive inhibition of ACP (acid phosphatase) and ALP (alkaline phosphatase).[5]
Biochem/physiol Actions
Myristicin induces the expression of glutathione S-transferase and cytochrome P450 (Cyp1a-1) in liver cells. May enhance detoxification of carcinogenic substances.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
STOT SE 3
Target Organs
Central nervous system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Myristicin: a potential cancer chemopreventive agent from parsley leaf oil
Zheng GQ, et al.
Journal of Agricultural and Food Chemistry, 40(1), 107-110 (1992)
H G Jeong et al.
Biochemical and biophysical research communications, 233(3), 619-622 (1997-04-28)
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
Nutmeg Intoxication Associated with Consumption as a Stupefacient
Gunaydin M, et al.
Journal of academic emergency medicine case reports, 8(3), 449-449 (2017)
Enzyme inhibition by molluscicidal components of Myristica fragrans Houtt. in the nervous tissue of snail Lymnaea acuminata
Jaiswal P, et al.
Enzyme Research, 2010(1), 49-56 (2010)
H S Lee et al.
Journal of chromatography. B, Biomedical sciences and applications, 705(2), 367-372 (1998-04-01)
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. From in vitro and in vivo metabolism of myristicin, the two metabolites 5-allyl-1-methoxy-2,3-dihydroxybenzene and 1'-hydroxymyristicin were identified using GC-MS
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