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]


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
Canonical SMILES: COC1=CC=C(C=C1)C(=O)C=C

See Also

1. Evaluation of human interindividual variation in bioactivation of estragole using physiologically based biokinetic modeling.
Punt A, Jeurissen SM, Boersma MG, Delatour T, Scholz G, Schilter B, van Bladeren PJ, Rietjens IM. PubMed: 19920071
2. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats.
Punt A, Paini A, Boersma MG, Freidig AP, Delatour T, Scholz G, Schilter B, van Bladeren PJ, Rietjens IM. PubMed PMID: 19447879
3. Characterization of the biliary and urinary glutathione and N-acetylcysteine metabolites of the hepatic carcinogen 1'-hydroxysafrole and its 1'-oxo metabolite in rats and mice.
Fennell TR, Miller JA, Miller EC. PubMed PMID: 6744260
4. Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice.
Wiseman RW, Miller EC, Miller JA, Liem A. PubMed PMID: 3567921
5. Carcinogenic and mutagenic activities of safrole, 1'-hydroxysafrole, and some known or possible metabolites.
Wislocki PG, Miller EC, Miller JA, McCoy EC, Rosenkranz HS. PubMed PMID: 192464
6. Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1'-hydroxyestragole.
Phillips DH, Miller JA, Miller EC, Adams B. PubMed PMID: 6969628
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