Flavor ingredient regulatory record

4,5-Epoxy-(E)-2-decenal

4,5-Epoxy-(E)-2-decenal is an aldehyde in the fruity family, FEMA GRAS under FEMA number 4037 (CAS 188590-62-7). Its odor is fruity, green, citrus, floral, fresh.

FEMA
4037
CAS
188590-62-7
JECFA
1570
Formula
C10H16O2

GRAS status: FEMA GRAS, publication 21. Recorded by FDA in the Substances Added to Food inventory under CAS 134454-31-2.

Structure

2D structure of 4,5-Epoxy-(E)-2-decenal
Structure of 4,5-Epoxy-(E)-2-decenal, C10H16O2. Drawn from the canonical SMILES.

Identity

IUPAC name (E)-3-[(2S,3S)-3-pentyloxiran-2-yl]prop-2-enal
CAS number 188590-62-7
FEMA number 4037
Molecular formula C10H16O2
Molecular weight 168.24 g/mol
SMILES CCCCC[C@@H]1O[C@H]1/C=C/C=O
InChIKey HIOMEXREAUSUBP-MLXLLJIISA-N
PubChem CID 15825667
Chemical class Aldehyde
Boiling point -83 °C
Flash point 93 °C

Also known as: 2-Propenal, 3-(3-pentyl-2-oxiranyl)-, (2E)-, 2-Propenal, 3-(3-pentyloxiranyl)-, (E)-, 2-Propenal, 3-(3-pentyloxiranyl)-, (2E)-, (2E)-3-(3-Pentyl-2-oxiranyl)-2-propenal, trans-4,5-epoxy-(e)-2-decenal, 4,5-epoxydec-2(trans)-enal, 4,5-epoxy-2-decenal, (2e)-, 2-propenal, 3-(3-pentyloxiranyl)-, (e)-, 3-(3-pentyloxiran-2-yl) prop-(e)-2-enal, 2-propenal, 3-(3-pentyloxiranyl)-, (2e)-, 4,5-epoxy-(e)-2-decenal [fifh], 2-propenal, 3-(3-pentyl-2-oxiranyl)-, (2e)-.

Can 4,5-Epoxy-(E)-2-decenal be labeled natural?

Nature makes 4,5-Epoxy-(E)-2-decenal, which is why the US label turns on process. A natural route gives natural flavor; synthesis gives artificial 4,5-Epoxy-(E)-2-decenal, same molecule. In the EU and UK the natural claim likewise needs the natural route, while Mercosur and Mexico keep a third class, identical-to-natural, for the synthetic material.

United States
Natural or artificial, by process
European Union and UK
Natural only from natural material
Mercosur and Mexico
Natural or identical-to-natural

How each market defines the classes: natural vs artificial flavor under 21 CFR 101.22.

Regulatory status, with citations

United States

4,5-Epoxy-(E)-2-decenal is FEMA GRAS under FEMA number 4037. It is cited in the Code of Federal Regulations at 21 CFR 172.515.

21 CFR 172.515

European Union and United Kingdom

4,5-Epoxy-(E)-2-decenal was on the Union List of flavouring substances as FL 16.071 when Regulation (EU) 872/2012 adopted the list, and the entry has since been withdrawn. It does not appear in the current consolidated text of Regulation (EC) 1334/2008. Check the amending regulations for the conditions that applied to existing stock, and treat EU or UK use as closed unless another route covers it.

JECFA (WHO / FAO)

JECFA number 1570, evaluated at the 69th meeting in 2008. No safety concern at current levels of intake when used as a flavouring agent.

JECFA monograph

Other US flags

Not on the California Proposition 65 list.

Odor and taste

Odor: Fruity, green, citrus, floral, fresh.

Where it is used

4,5-Epoxy-(E)-2-decenal is used in beverage, confection, fruit flavors, savory dishes and sauces, typically as a fruity note.

Structurally similar flavor ingredients

Flavor ingredients with a GRAS determination closest to 4,5-Epoxy-(E)-2-decenal by structure. Whether one can replace it is a sensory and regulatory call; the reformulation tool works that through.

MaterialFEMASimilarityOccurrence
2,3-Epoxyheptanal465884%Not determined
Ethyl methyl-p-tolylglycidate375766%In nature
N-Cyclopropyl (E)-2,(Z)-6-nonadienamide408764%In nature
trans-Carvone-5,6-oxide408457%In nature
Ethyl 3-phenyl-2,3-epoxypropionate245457%In nature

More aldehydes in this index

cis-6-Nonenal · 2,4-Nonadienal · (+/-)-2-(5-Methyl-5-vinyl-tetrahydrofuran-2-yl)propionaldehyde · Undecanal · 2-trans,6-trans Nonadienal · 2-Ethylbutyraldehyde

4,5-Epoxy-(E)-2-decenal FAQ

Is 4,5-Epoxy-(E)-2-decenal on the FEMA GRAS list?

It is. FEMA number 4037 covers 4,5-Epoxy-(E)-2-decenal. The Code of Federal Regulations lists it at 21 CFR 172.515.

What is the FEMA number for 4,5-Epoxy-(E)-2-decenal?

The FEMA number for 4,5-Epoxy-(E)-2-decenal is 4037 and its CAS registry number is 188590-62-7. Its flavor category is fruity.

What is 4,5-Epoxy-(E)-2-decenal used for?

4,5-Epoxy-(E)-2-decenal is described as fruity, green, citrus, floral, fresh. It shows up in beverage, confection, fruit flavors, savory dishes and sauces.

What did JECFA conclude about 4,5-Epoxy-(E)-2-decenal?

JECFA evaluated 4,5-Epoxy-(E)-2-decenal at the 69th meeting in 2008 under JECFA number 1570. The panel concluded: No safety concern at current levels of intake when used as a flavouring agent.

Is 4,5-Epoxy-(E)-2-decenal approved in the EU?

No EU FL number is on file for 4,5-Epoxy-(E)-2-decenal. It has a JECFA evaluation (JECFA 1570), which the EU list draws on, but the Union List entry itself should be confirmed before EU use.

Is 4,5-Epoxy-(E)-2-decenal natural or artificial?

The process decides for 4,5-Epoxy-(E)-2-decenal. It occurs in nature, so a natural-source, natural-process material is natural flavor in the US and synthetic 4,5-Epoxy-(E)-2-decenal is artificial. In the EU and UK the natural claim likewise needs the natural route, while Mercosur and Mexico keep a third class, identical-to-natural, for the synthetic material.

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Sources and attribution. The identity and regulatory facts on this page are taken from the FDA Substances Added to Food inventory, a US government record, which lists this substance as 4,5-EPOXY-(E)-2-DECENAL under CAS 134454-31-2 and carries its FEMA number, its JECFA flavor number. The inventory is searchable at FDA. FDA records its technical effect as flavoring agent or adjuvant.

A FEMA GRAS conclusion is reached by the Expert Panel of the Flavor and Extract Manufacturers Association of the United States, and the FEMA number names that conclusion. FEMA publishes its own entry for this substance in the FEMA Flavor Library, which is the authoritative record of what the Panel decided and is worth reading alongside this page.

Ambrose Compliance is not affiliated with, endorsed by, or sponsored by FEMA. FEMA and FEMA GRAS are used here as identifiers for a published regulatory determination, not as marks of any relationship between FEMA and Ambrose.

About this page. Facts come from the FDA Substances Added to Food inventory, the Code of Federal Regulations, the EPA TSCA Inventory, the EU Union List, JECFA and the Ambrose database, with FEMA's published determination cited where it applies; parts of the text are written by Ambrose AI, which can make mistakes. Check the cited source before relying on anything here. This is not regulatory or legal advice.