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M9411

Sigma-Aldrich

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:
607-91-0
Molecular Weight:
192.21
EC Number:
210-146-9
MDL number:
MFCD00133549
UNSPSC Code:
12352205
PubChem Substance ID:
24897334
NACRES:
NA.77

Quality Level

200

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

Related Categories

General description

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

Application

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

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Repr. 2 - STOT SE 3

target_organs

Central nervous system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
G Q Zheng et al.
Carcinogenesis, 13(10), 1921-1923 (1992-10-01)
Glutathione S-transferase (GST) assay-guided fractionation of parsley leaf oil from the edible plant Petroselinum sativum Hoffm. (Umbelliferae) led to the isolation of myristicin. Myristicin showed high activity as an inducer of the detoxifying enzyme GST in the liver and small
H Ahmad et al.
Biochemical and biophysical research communications, 236(3), 825-828 (1997-07-30)
The present studies were undertaken to elucidate the mechanism of induction of glutathione S-transferase (GST) in mouse liver by myristicin, an active constituent of parsley leaf. A/J albino mice, given 5 to 50 mg doses of myristicin, showed 4- to
Allelochemical induction of cytochrome P450 monooxygenases and amelioration of xenobiotic toxicity in Helicoverpa zea
Zeng RS, et al.
Journal of Chemical Ecology, 33(3), 449-449 (2007)
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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