3,4-methylenedioxycinnamoyl glycine

3,4-Methylenedioxycinnamoyl glycine is an alkaloid metabolite that occurs in rats and mice injected with 3'-Hydroxyisosafrole.[1]

It is suspected of also occurring in humans after the ingestion of safrole.

Theoretical Metabolite Route

It's possible that the aldehyde 3,4-methylenedioxycinnamaldehyde could be a transient step between 3,4-methylenedioxycinnamoyl glycine and 3'-Hydroxyisosafrole. Glycine is able to form adducts with some aldehydes. See Cinnamaldehyde for more details.

3'-hydroxyisosafrole 3'-hydroxyisosafrole is oxidized to
3,4-methylenedioxycinnamaldehyde condenses with glycine to form 3,4-methylenedioxycinnamoyl glycine
3,4-methylenedioxycinnamaldehyde.png 3%2C4-methylenedioxycinnamoyl%20glycine.png

Chemical Properties

Synonyms: SCHEMBL9508315; N-[(2E)-3-(1,3-Benzodioxol-5-yl)-2-propenoyl]glycine; Glycine, N-[(2E)-3-(1,3-benzodioxol-5-yl)-1-oxo-2-propen-1-yl]-;
IUPAC Name: 2-[[(E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]amino]acetic acid
PubChem CID: 19762233
ChemSpider ID: 14402698
Molecular Formula: C12H11NO5
Molecular Weight: 249.222 g/mol
Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=CC(=O)NCC(=O)O
Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C/C(=O)NCC(=O)O
XLogP3: 1.4

See Also

1. The metabolic sulfonation and side-chain oxidation of 3'-hydroxyisosafrole in the mouse and its inactivity as a hepatocarcinogen relative to 1'-hydroxysafrole.
Boberg EW, Miller EC, Miller JA. PMID: 3757147
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