Flavor ingredient regulatory record

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal is an acetal in the vanilla family, FEMA GRAS under FEMA number 3904 (CAS 180964-47-0). Its odor is sweet, creamy, vanilla, minty, fresh.

FEMA
3904
CAS
180964-47-0
JECFA
1879
EU FL
02.248
Formula
C21H32O5

GRAS status: FEMA GRAS, publication 18. Recorded by FDA in the Substances Added to Food inventory under CAS 180964-47-0.

Structure

2D structure of Vanillin 3-(l-menthoxy)propane-1,2-diol acetal
Structure of Vanillin 3-(l-menthoxy)propane-1,2-diol acetal, C21H32O5. Drawn from the canonical SMILES.

Identity

IUPAC name 2-methoxy-4-[4-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxymethyl]-1,3-dioxolan-2-yl]phenol
CAS number 180964-47-0
FEMA number 3904
Molecular formula C21H32O5
Molecular weight 364.48 g/mol
SMILES COc1cc(C2OCC(CO[C@@H]3C[C@H](C)CC[C@H]3C(C)C)O2)ccc1O
InChIKey ZOGKSXQLOOQXFG-LTKHDUQWSA-N
PubChem CID 9969062
Chemical class Acetal

Also known as: Phenol, 2-methoxy-4-[4-[[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]-1,3-dioxolan-2-yl]-, 2-Methoxy-4-[4-[[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]-1,3-dioxolan-2-yl]phenol, 4-(Menthoxymethyl)-2-(3′-methoxy-4′-hydroxyphenyl)-1,3-dioxolane, 4-(1-Menthoxymethyl)-2-(3′-methoxy-4′-hydroxyphenyl)-1,3-dioxolane, 2-methoxy-4-(4-(((5-methyl-2-(1-methylethyl)cyclohexyl)oxy)methyl)-1,3-dioxolan-2-yl)-phenol, phenol, 2-methoxy-4-(4-((((1r,2s,5r)-5-methyl-2-(1-methylethyl)cyclohexyl)oxy)methyl)-1,3-dioxolan-2-yl)-, vanillin 3-((-)-menthoxy)(+-)-propane-1,2-diol acetal, 2-methoxy-4-(4-(((5-methyl-2-(propan-2-yl)cyclohexyl)oxy)methyl)-1,3-dioxolan-2-yl)phenol, 2-methoxy-4-[4-({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}methyl)-1,3-dioxolan-2-yl]phenol, vanillin 3-((-)-menthoxy)(+/-)-propane-1,2-diol acetal, 2-methoxy-4-[4-({[(1r,2s,5r)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}methyl)-1,3-dioxolan-2-yl]phenol, 2-methoxy-4-[4-[[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxymethyl]-1,3-dioxolan-2-yl]phenol.

Can Vanillin 3-(l-menthoxy)propane-1,2-diol acetal be labeled natural?

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal occurs in nature, so the label depends on the route: vanillin 3-(l-menthoxy)propane-1,2-diol acetal won from a natural source by a physical, enzymatic or microbiological process is natural flavor in the United States, and synthesized vanillin 3-(l-menthoxy)propane-1,2-diol acetal 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.

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

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal is FEMA GRAS under FEMA number 3904. 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 02.248, Annex I Part A under Regulation (EC) 1334/2008, evaluation status approved (EFSA). The UK retains the same list.

JECFA (WHO / FAO)

JECFA number 1879, 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

Odor: Sweet, creamy, vanilla, minty, fresh.

Where it is used

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal is used in beverage, confection, dairy, bakery and flavoring, typically as a vanilla note.

Structurally similar flavor ingredients

Flavor ingredients with a GRAS determination closest to Vanillin 3-(l-menthoxy)propane-1,2-diol acetal by structure. Whether one can replace it is a sensory and regulatory call; the reformulation tool works that through.

MaterialFEMASimilarityOccurrence
Rebaudioside A460180%In nature
Santalyl phenylacetate300878%In nature
Neohesperidin dihydrochalcone381178%In nature
Naringin dihydrochalcone449577%Not determined

More acetals in this index

Ethyl vanillin propylene glycol acetal · Vanillin propylene glycol acetal · Vanillin erythro- & threo-butan-2,3-diol acetal · Acetaldehyde di-cis-3-hexenyl acetal · Hydroxycitronellal dimethyl acetal · Hydroxycitronellal diethyl acetal

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal FAQ

Does vanillin 3-(l-menthoxy)propane-1,2-diol acetal have FEMA GRAS status?

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal holds FEMA GRAS status under FEMA number 3904. It is also codified at 21 CFR 172.515.

How do I cite vanillin 3-(l-menthoxy)propane-1,2-diol acetal by FEMA or CAS number?

Cite vanillin 3-(l-menthoxy)propane-1,2-diol acetal as FEMA 3904 or CAS 180964-47-0; both point to the same entry. FEMA files it in the vanilla flavor category.

Can vanillin 3-(l-menthoxy)propane-1,2-diol acetal be labeled a natural flavor?

Since vanillin 3-(l-menthoxy)propane-1,2-diol acetal is found in nature, US labeling follows how it was obtained: natural flavor from a natural source and a natural process, artificial when vanillin 3-(l-menthoxy)propane-1,2-diol acetal is synthesized. 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.

Can vanillin 3-(l-menthoxy)propane-1,2-diol acetal be used in the EU and UK?

Vanillin 3-(l-menthoxy)propane-1,2-diol acetal is on the EU Union List of flavouring substances as FL 02.248 (Annex I Part A) under Regulation 1334/2008.

Has JECFA evaluated vanillin 3-(l-menthoxy)propane-1,2-diol acetal?

Yes. JECFA number 1879, evaluated at the 68th meeting in 2007. Conclusion: no safety concern at current levels of intake.

What does vanillin 3-(l-menthoxy)propane-1,2-diol acetal smell and taste like, and where is it used?

The odor of vanillin 3-(l-menthoxy)propane-1,2-diol acetal is sweet, creamy, vanilla, minty, fresh. Typical uses are beverage, confection, dairy, bakery and flavoring.

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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 VANILLIN 3-(L-MENTHOXY)PROPANE-1,2-DIOL ACETAL under CAS 180964-47-0 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.