ethylzingerone

CHEBI:172922 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by ethoxy and hydroxy groups, respectively. It is a preservative with antimicrobial activity and a good safety profile that has been approved for use in cosmetics. It is structurally similar to zingerone, a phytochemical found in the root of the ginger plant Zingiber officinale. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:33853
• Label unavailable CHEBI:35618
• Label unavailable CHEBI:51867

Chemical structure

SMILES

CCOc1cc(CCC(C)=O)ccc1O

InChI

InChI=1S/C12H16O3/c1-3-15-12-8-10(5-4-9(2)13)6-7-11(12)14/h6-8,14H,3-5H2,1-2H3

Also called

• 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (EXACT_SYNONYM)— chebi
• 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone (EXACT_SYNONYM)— chebi
• HEPB (EXACT_SYNONYM)— chebi
• hydroxyethoxyphenyl butanone (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

• cas:569646-79-3
• chemspider:24208550

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• antimicrobial cosmetic preservative CHEBI:172949
• antibacterial agent CHEBI:33282
• antifungal agent CHEBI:35718

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

intracellular oxidation and associated bacterial stress responses BIOLOGICAL_PROCESS DOWNSTREAM_AFFECTED_PROCESS

Multi-omics and genetic screens linked ethylzingerone exposure to oxidative damage, electrophile defense, oxidized-protein repair, pH homeostasis, permeability, and lipopolysaccharide pathways without identifying a direct binding target. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2020-09 (retrieved 2026-09-02).

• PMID:32737133 (Primary Burkholderia susceptibility, multi-omics, and mechanism study (DOI:10.1128/AEM.01808-20).)

Mechanism summary

Mode of action

MULTIPLE host shared target — CURATOR: PMID:32737133 combined susceptibility testing, transposon mutagenesis, transcriptomics, and resequencing in Burkholderia. Killing was multifactorial, with intracellular oxidation central and associated changes in stress responses, permeability, pH homeostasis, macromolecular repair, and lipopolysaccharide biology; no single direct molecular target was shown.

Record-level evidence

• PMID:32737133 (Primary exact-ethylzingerone Burkholderia efficacy and multifactorial-mechanism study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, antibacterial and preservative roles, and class; added the experimentally supported multifactorial mode and downstream oxidative-stress process while recording the absent direct target.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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