# Methyl heptanoate

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Methyl heptanoate Names IUPAC name Methyl heptanoate Other names Methyl heptylate Methyl enanthate Methyl oenanthate Heptanoic acid, methyl ester Identifiers CAS Number 106-73-0 Y 3D model (JSmol) Interactive image ChEBI CHEBI:88620 ChemSpider 7538 Y ECHA InfoCard 100.003.118 EC Number 203-428-8 PubChem CID 7826 UNII 1J543V5703 CompTox Dashboard (EPA) DTXSID3059345 InChI Key: XNCNNDVCAUWAIT-UHFFFAOYSA-N InChI=1S/C8H16O2/c1-3-4-5-6-7-8(9)10-2/h3-7H2,1-2H3 SMILES CCCCCCC(=O)OC Properties Chemical formula C8H16O2 Molar mass 144.214 g·mol−1 Appearance Colorless liquid[1] Density 0.880 g/cm3 (20 °C)[1] Melting point −56 °C (−69 °F; 217 K)[1] Boiling point 171–172 °C (340–342 °F; 444–445 K)[1] Solubility in water Insoluble in water[1] Hazards GHS labelling:[1] Pictograms Signal word Warning Hazard statements H226, H315 Precautionary statements P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P321, P332+P317, P362+P364, P370+P378, P403+P235, P501 Flash point 52 °C (126 °F; 325 K)[1] Lethal dose or concentration (LD, LC): LD50 (median dose) > 5,000 mg/kg (oral, rat) > 5,000 mg/kg (dermal, rabbit) Related compounds Related compounds Methyl formate Methyl acetate Methyl propionate Methyl butyrate Methyl pentanoate Methyl hexanoate Methyl octanoate Methyl nonanoate Methyl decanoate Methyl laurate Ethyl heptanoate Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

**Methyl heptanoate** is an [organic compound](/source/Organic_compound) with the chemical formula CH3(CH2)5CO2CH3. It is the [methyl](/source/Methyl) [ester](/source/Ester) of [heptanoic acid](/source/Heptanoic_acid) (also known as enanthic acid). This [fatty acid ester](/source/Fatty_acid_ester) is a colorless, oily liquid with a fruity, wine-like odor that is used in the [flavor](/source/Flavor_industry) and [fragrance industries](/source/Perfume_industry).[1]

## Properties

Methyl heptanoate is a colorless to pale yellow liquid at room temperature. It has a characteristic [orris](/source/Orris_oil), winey, brandy-like aroma with cognac and fruity undertones.[2][3] The compound is practically insoluble in water but miscible with most organic solvents and oils.

## Occurrence and production

Methyl heptanoate occurs naturally in trace amounts in some fruits and fermented products. It has been identified as a volatile component in fruits such as strawberries, grapes, and wine and in flowering plants such as *[Astragalus](/source/Astragalus_(plant))*.[4]

Commercially, it is produced by [esterification](/source/Esterification) of [heptanoic acid](/source/Heptanoic_acid) with [methanol](/source/Methanol) in the presence of an acid catalyst (typically sulfuric acid) or via [transesterification](/source/Transesterification) of [triglycerides](/source/Triglyceride) containing heptanoic acid. It is also available through the [methanolysis](/source/Methanolysis) of natural oils that contain other heptanoate esters.[5]

## Uses

Methyl heptanoate is primarily used in the flavor and fragrance industry:[3][6]

- As a component of artificial cognac, brandy, wine, and fruit flavorings

- In perfumes to impart green, fruity, and winey notes

- As a trace ingredient in strawberry, grape, and other fruit flavor compositions

It is approved as a [flavoring agent](/source/Flavoring_agent) in many countries and has the [FEMA number](/source/FEMA_number) 2705.[7]

## Safety

Methyl heptanoate has low acute toxicity; its [LD50s](/source/Median_lethal_dose) include > 5,000 mg/kg (oral, rat) and > 5,000 mg/kg (dermal, rabbit).[8] It may cause mild skin and eye irritation upon direct contact. The compound is combustible, but does not present a fire or explosion hazard beyond those typical of flammable esters.

## References

1. ^ [***a***](#cite_ref-GESTIS_1-0) [***b***](#cite_ref-GESTIS_1-1) [***c***](#cite_ref-GESTIS_1-2) [***d***](#cite_ref-GESTIS_1-3) [***e***](#cite_ref-GESTIS_1-4) [***f***](#cite_ref-GESTIS_1-5) [***g***](#cite_ref-GESTIS_1-6) [Record](https://gestis.dguv.de/data?name=101660&lang=en) in the [GESTIS Substance Database](/source/GESTIS_Substance_Database) of the [Institute for Occupational Safety and Health](/source/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance)

1. **[^](#cite_ref-2)** ["Methyl hepatanoate"](https://www.thegoodscentscompany.com/data/rw1017861.html). *thegoodscentscompany.com*.

1. ^ [***a***](#cite_ref-Arctander_3-0) [***b***](#cite_ref-Arctander_3-1) Arctander, Steffen (1969). *Perfume and Flavor Chemicals*. Montclair, NJ.{{[cite book](https://en.wikipedia.org/wiki/Template:Cite_book)}}: CS1 maint: location missing publisher ([link](https://en.wikipedia.org/wiki/Category:CS1_maint:_location_missing_publisher))

1. **[^](#cite_ref-4)** Miyazawa, Mitsuo; Kameoka, Hiromu (1987). "Volatile Flavor Components of ASTRAGALI RADIX ( *Astragalus membranaceus* Bunge)". *Agricultural and Biological Chemistry*. **51** (11): 3153–3154. [doi](/source/Doi_(identifier)):[10.1080/00021369.1987.10868496](https://doi.org/10.1080%2F00021369.1987.10868496).

1. **[^](#cite_ref-5)** Vonortas, Andreas; Papayannakos, Nikolaos (2014). "Comparative analysis of biodiesel versus green diesel". *WIREs Energy and Environment*. **3** (1): 3–23. [Bibcode](/source/Bibcode_(identifier)):[2014WIREE...3....3V](https://ui.adsabs.harvard.edu/abs/2014WIREE...3....3V). [doi](/source/Doi_(identifier)):[10.1002/wene.78](https://doi.org/10.1002%2Fwene.78).

1. **[^](#cite_ref-Burdock_6-0)** Burdock, George A. (2010). *Fenaroli's Handbook of Flavor Ingredients*, 6th ed. CRC Press.

1. **[^](#cite_ref-7)** ["2705: Methyl heptanoate"](https://www.femaflavor.org/flavor-library/methyl-heptanoate). *femaflavor.org*.

1. **[^](#cite_ref-8)** ["Safety Data Sheet"](https://www.sigmaaldrich.com/US/en/sds/sial/75218). *sigmaaldrich.com*.

v t e Esters Methyl esters Methyl formate Methyl acetate Methyl propionate Methyl butyrate Methyl pentanoate Methyl hexanoate Methyl heptanoate Methyl benzoate Ethyl esters Ethyl formate Ethyl acetate Ethyl propionate Ethyl butyrate Ethyl pentanoate Ethyl hexanoate Ethyl heptanoate Ethyl octanoate Ethyl decanoate Ethyl palmitate Ethyl benzoate Propyl esters Propyl acetate Propyl propanoate Propyl benzoate Isopropyl acetate Isopropyl palmitate Butyl esters Butyl acetate Butyl butyrate Isobutyl acetate sec-Butyl acetate tert-Butyl acetate Amyl esters Amyl acetate Pentyl propanoate Pentyl butyrate Pentyl pentanoate Pentyl hexanoate Isoamyl formate Isoamyl acetate Sec-Amyl acetate Hexyl esters Hexyl acetate Phenyl esters Phenyl acetate Heptyl esters Heptyl acetate Heptyl butyrate Benzyl esters Benzyl acetate Benzyl benzoate

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Adapted from the Wikipedia article [Methyl heptanoate](https://en.wikipedia.org/wiki/Methyl_heptanoate) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Methyl_heptanoate?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.