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Merck

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
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
210-146-9
MDL number:

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Product Name

Myristicin from parsley leaf oil, ≥85% (HPLC), oil

InChI key

BNWJOHGLIBDBOB-UHFFFAOYSA-N

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

SMILES string

COc1cc(CC=C)cc2OCOc12

assay

≥85% (HPLC)

form

oil

color

clear light yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

Application

Myristicin from parsley leaf oil has been used to study competitive and uncompetitive inhibition of ACP (acid phosphatase) and ALP (alkaline phosphatase).[1]

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.

General description

Myristicin, a phenylpropene, is an essential oil component.[2] It has anticholinergic and psychotropic activities.[3] Myristicin blocks cytochrome P450 monooxygenases, which detoxifies furanocoumarins.[2] It functions as a serotonin receptor agonist and hallucinogenic agent.[3] Myristicin stimulates glutathione S-transferase activity and might function as a chemopreventive agent.[4] It acts as a precursor for the metabolite 3,4- methylenedioxymethamphetamine (MDMA).[5]

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

STOT SE 3

target_organs

Central nervous system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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
H G Jeong et al.
Biochemical and biophysical research communications, 217(3), 966-971 (1995-12-26)
The effect of myristicin on the expression of liver cytochrome P450s and its mRNA levels was examined in rats. Treatment of rats with myristicin (i.p., 500 mumol/kg) caused 2-20 fold increases in liver P450 1A1/2, 2B1/2, and 2E1 enzyme activities
Nutmeg Intoxication Associated with Consumption as a Stupefacient
Gunaydin M, et al.
Journal of academic emergency medicine case reports, 8(3), 449-449 (2017)
Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells
Lee BK, et al.
Toxicology Letters, 157(1), 49-56 (2005)

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