4-Methoxycinnamoylglycine is an alkaloid metabolite of methyl chavicol detected in human urine after the oral ingestion of methyl chavicol.[1]

4-Methoxycinnamoylglycine should form in the exact same way that cinnamoylglycine forms from the aldehyde cinnamaldehyde in humans. In humans cinnamoylglycine is the glycine conjugate of cinnamic acid, an intermediate metabolite of cinnamaldehyde created by aldehyde dehydrogenase. Likewise, 4-methoxycinnamoylglycine should be the glycine conjugate of 4-methoxycinnamic acid, which should be an intermediate metabolite created by aldehyde dehydrogenase from a presumed aldehyde metabolite of methyl chavicol known as 4-methoxycinnamaldehyde. The existence of this alkaloid metabolite of methyl chavicol is strong evidence that an aldehyde forms from methyl chavicol in vivo in humans.

Metabolic Route to 4-Methoxycinnamoylglycine

This gives the presumed metabolic route to 4-methoxycinnamoylglycine from methyl chavicol. All of these steps are proven to occur for the very closely related methyl eugenol and likewise probably occur for methyl chavicol.

Methyl chavicol is ingested:


Unknown P450 enzymes create 3'-hydroxyanethole:


CYP2E1 or alcohol dehydrogenase create 4-methoxycinnamaldehyde:


Aldehyde dehydrogenase creates 4-methoxycinnamic acid:


4-Methoxycinnamic acid is conjugated with glycine to give 4-methoxycinnamoylglycine:


Chemical Properties

Synonyms: N-(4-methoxycinnamoyl)glycine
ChemSpider ID: 12249715
PubChem Compound ID: 3401706
Molecular Weight: 235.23592 [g/mol]
Molecular Formula: C12H13NO4
XLogP3-AA: 1.2
H-Bond Donor: 2
H-Bond Acceptor: 4
IUPAC Name: 2-[3-(4-methoxyphenyl)prop-2-enoylamino]acetic acid
InChI: InChI=1S/C12H13NO4/c1-17-10-5-2-9(3-6-10)4-7-11(14)13-8-12(15)16/h2-7H,8H2,1H3,(H,13,14)(H,15,16)
Canonical SMILES: COC1=CC=C(C=C1)C=CC(=O)NCC(=O)O

1. The metabolic disposition of [methoxy-14C]-labelled trans-anethole, estragole and p-propylanisole in human volunteers.
Sangster SA, Caldwell J, Hutt AJ, Anthony A, Smith RL. PubMed: 3424869
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