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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

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. 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

Signal Word

Warning

Hazard Statements

H336,H361f,H412

Hazard Classifications

Aquatic Chronic 3 - Repr. 2 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells
Lee BK, et al.
Toxicology Letters, 157(1), 49-56 (2005)
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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