Flavor ingredient regulatory record

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide is a carboxamide in the cooling family, FEMA GRAS under FEMA number 4309 (CAS 68489-14-5).

FEMA
4309
CAS
68489-14-5
JECFA
1776
EU FL
16.111
Formula
C15H27NO3

GRAS status: FEMA GRAS, publication 23. Recorded by FDA in the Substances Added to Food inventory under CAS 68489-14-5.

Structure

2D structure of N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide
Structure of N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, C15H27NO3. Drawn from the canonical SMILES.

Identity

IUPAC name ethyl 2-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate
CAS number 68489-14-5
FEMA number 4309
Molecular formula C15H27NO3
Molecular weight 269.38 g/mol
SMILES CCOC(=O)CNC(=O)[C@@H]1C[C@H](C)CC[C@H]1C(C)C
InChIKey GWRCTWAPTXBPHW-FRRDWIJNSA-N
PubChem CID 11615984
FDA UNII Q6CA504696
EPA DTXSID DTXSID501134437
Chemical class Carboxamide
Boiling point 151 °C

Also known as: Glycine, N-[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]-, ethyl ester, Glycine, N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]-, ethyl ester, [1R-(1α,2β,5α)]-, N-[[(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester, CPS 337, Ethyl 3-(p-menthane-3-carboxamido)acetate, FEMA 4309, n-((ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, ethyl 2-[[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate, n-[[(1r,2s,5r)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester, winsense ws-5, ethyl 2-(((1r,2s,5r)-2-isopropyl-5-methyl-cyclohexanecarbonyl)amino)acetate, glycine, n-(((1r,2s,5r)-5-methyl-2-(1-methylethyl)cyclohexyl)carbonyl)-, ethyl ester.

Can N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide be labeled natural?

Nature occurrence: Not yet found in nature (provisional).

Nature occurrence has not been settled for this substance, so the natural or artificial class is not stated here. The FEMA GRAS status does not depend on it.

Regulatory status, with citations

United States

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide is FEMA GRAS under FEMA number 4309. It is cited in the Code of Federal Regulations at 21 CFR 172.515.

21 CFR 172.515

European Union and United Kingdom

Listed on the Union List of flavouring substances as FL 16.111, Annex I Part A under Regulation (EC) 1334/2008, evaluation status approved (EFSA). The UK retains the same list.

JECFA (WHO / FAO)

JECFA number 1776, evaluated at the 68th meeting in 2007. no safety concern at current levels of intake.

JECFA monograph

Other US flags

Not on the California Proposition 65 list.

Odor and taste

Taste: Clean cooling, less minty than menthol.

Where it is used

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide is used in cooling agent, beverage and confection, typically as a cooling note.

Structurally similar flavor ingredients

Flavor ingredients with a GRAS determination closest to N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide by structure. Whether one can replace it is a sensory and regulatory call; the reformulation tool works that through.

MaterialFEMASimilarityOccurrence
N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide454975%Not determined
WS-3345575%In nature
Capsaicin340474%In nature
mono-Menthyl succinate381073%In nature
Nonanoyl 4-hydroxy-3-methoxybenzylamide278773%In nature

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide FAQ

Does N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide have FEMA GRAS status?

N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide holds FEMA GRAS status under FEMA number 4309. The Code of Federal Regulations lists it at 21 CFR 172.515.

How do I cite N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide by FEMA or CAS number?

Cite N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide as FEMA 4309 or CAS 68489-14-5; both point to the same entry. Its flavor category is cooling.

What did JECFA conclude about N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide?

JECFA evaluated N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide at the 68th meeting in 2007 under JECFA number 1776. The panel concluded: no safety concern at current levels of intake.

Can N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide be used in the EU and UK?

Yes. FL 16.111 is the Union List entry for N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide, annex I Part A, under Regulation 1334/2008, and the UK keeps the same list.

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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 N-[(ETHOXYCARBONYL)METHYL)-P-MENTHANE-3-CARBOXAMIDE under CAS 68489-14-5 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.