
1'-Oxoestragole is a phenyl vinyl ketone metabolite produced by rats fed 1'-hydroxyestragole (the 1'-hydroxy metabolite of the allylbenzene methyl chavicol).[2] It has also been produced in vitro in human liver exposed to 1'-hydroxyestragole.[2]
1'-Oxoestragole was found to have no carcinogenic potential in mice.[2]
1'-Oxoestragole is created from 1'-hydroxyestragole by the action of estradiol-17beta-dehydrogenase (17beta-HSD2).[1]
Reactivity
1′-Oxoestragole forms adducts with glutathione and N-acetylcysteine without the need for a catalyst.[3];
1'-Oxoestragole was found to form adducts with guanosine and 2′-deoxyguanosine in a direct reaction with these nucleosides[6]. Regardless, 1′-oxoestragole was not found to be carcinogenic in vivo in mice [4]. The lack of carcinogenicity is caused by extensive detoxification of 1′-oxoestragole via conjugation with glutathione, N-acetylcysteine, or endogenous amines (Fennell et al., 1984[3]; Wislocki et al., 1977[5]).
The 2',3'-double bond of 1'-oxoestragole may possibly react with amines such as dimethylamine, piperidine, and pyrrolidine at room temperature without enzymes to form the corresponding 3'-addition products leading to alkaloids of potential psychoactivity. This is proven to be the case for the closely related 1'-oxosafrole.[5]
Non-Psychedelic Metabolites
1'-Oxoestragole is capable of forming adducts with glutathione (GSH) leading to inactivation.[1] Adducts with glutathione (GSH) are formed by the action of UGT2B7 and UGT1A9.
Psychedelic Alkaloid Metabolites
1'-Oxoestragole is capable of forming adducts with endogenous amines.[1] This action is believed to be responsible for the psychedelic effects methyl chavicol is capable of producing in humans under certain conditions.
The alkaloids in this section are all adducts of 1'-oxoestragole (a metabolite of methyl chavicol) and endogenous amines. Similar endogenous amine adducts are proven to form from myristicin, elemicin, and other similar allylbenzenes.
Dimethylamine Adduct

3-(dimethylamino)-1-(4-methoxyphenyl)propan-1-one is an adduct of 1'-oxoestragole and dimethylamine.
Piperidine Adduct

1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is an adduct of 1'-oxoestragole and piperidine.
Pyrrolidine Adduct

1-(4-methoxyphenyl)-3-pyrrolidin-1-ylpropan-1-one is an adduct of 1'-oxoestragole and pyrrolidine.
Chemical Properties
PubChem Compound ID: 24017
Molecular Weight: 162.1852 [g/mol]
Molecular Formula: C10H10O2
XLogP3: 2.3
H-Bond Donor: 0
H-Bond Acceptor: 2
IUPAC Name: 1-(4-methoxyphenyl)prop-2-en-1-one
InChI: InChI=1S/C10H10O2/c1-3-10(11)8-4-6-9(12-2)7-5-8/h3-7H,1H2,2H3
InChIKey: YMESWDPSFKMFND-UHFFFAOYSA-N
Canonical SMILES: COC1=CC=C(C=C1)C(=O)C=C