{{Chembox | Name = Methyl heptanoate | ImageFile = Methyl heptanoate v2.svg | ImageSize = 200px | ImageAlt = Skeletal formula of methyl heptanoate | IUPACName = Methyl heptanoate | OtherNames = Methyl heptylate<br>Methyl enanthate<br>Methyl oenanthate<br>Heptanoic acid, methyl ester | Section1 = {{Chembox Identifiers | CASNo = 106-73-0 | CASNo_Ref = {{cascite|correct|CAS}} | ChEBI = 88620 | ChemSpiderID = 7538 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EC_number = 203-428-8 | PubChem = 7826 | UNII = 1J543V5703 | SMILES = CCCCCCC(=O)OC | InChI = 1S/C8H16O2/c1-3-4-5-6-7-8(9)10-2/h3-7H2,1-2H3 | StdInChIKey = XNCNNDVCAUWAIT-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C = 8 | H = 16 | O = 2 | Appearance = Colorless liquid<ref name="GESTIS">{{GESTIS|ZVG=101660 }}</ref> | Density = 0.880 g/cm<sup>3</sup> (20 °C)<ref name="GESTIS"/> | MeltingPtC = −56 | MeltingPt_ref = <ref name="GESTIS"/> | BoilingPtC = 171–172 | BoilingPt_ref = <ref name="GESTIS"/> | Solubility = Insoluble in water<ref name="GESTIS"/> }} | Section7 = {{Chembox Hazards | FlashPtC = 52 | FlashPt_ref = <ref name="GESTIS"/> | AutoignitionPt = | LD50 = > 5,000 mg/kg (oral, rat)<br>> 5,000 mg/kg (dermal, rabbit) | GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/7826#section=Safety-and-Hazards] | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|226|315}} | PPhrases = {{P-phrases|210|233|240|241|242|243|264|280|302+352|303+361+353|321|332+317|362+364|370+378|403+235|501}} }} | Section9 = {{Chembox Related | OtherCompounds = {{ubl|[[Methyl formate]]|[[Methyl acetate]]|[[Methyl propionate]]|[[Methyl butyrate]]|[[Methyl pentanoate]]|[[Methyl hexanoate]]|[[Methyl octanoate]]|[[Methyl nonanoate]]|[[Methyl decanoate]]|[[Methyl laurate]]|[[Ethyl heptanoate]]}} }} }}
'''Methyl heptanoate''' is an [[organic compound]] with the chemical formula {{chem2|CH3(CH2)5CO2CH3}}. It is the [[methyl]] [[ester]] of [[heptanoic acid]] (also known as enanthic acid). This [[fatty acid ester]] is a colorless, oily liquid with a fruity, wine-like odor that is used in the [[flavor industry|flavor]] and [[Perfume industry|fragrance industries]].<ref name="GESTIS"/>
==Properties== Methyl heptanoate is a colorless to pale yellow liquid at room temperature. It has a characteristic [[orris oil|orris]], winey, brandy-like aroma with cognac and fruity undertones.<ref>{{cite web | url = https://www.thegoodscentscompany.com/data/rw1017861.html | website = thegoodscentscompany.com | title = Methyl hepatanoate }}</ref><ref name=Arctander>{{cite book | author = Arctander, Steffen | date = 1969 | title = Perfume and Flavor Chemicals | location = Montclair, NJ }}</ref> 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 (plant)|Astragalus]]''.<ref>{{cite journal | last1 = Miyazawa | first1 = Mitsuo | last2 = Kameoka | first2 = Hiromu | title = Volatile Flavor Components of ASTRAGALI RADIX ( ''Astragalus membranaceus'' Bunge) | journal = Agricultural and Biological Chemistry | date = 1987 | volume = 51 | issue = 11 | pages = 3153–3154 | doi = 10.1080/00021369.1987.10868496 }}</ref>
Commercially, it is produced by [[esterification]] of [[heptanoic acid]] with [[methanol]] in the presence of an acid catalyst (typically sulfuric acid) or via [[transesterification]] of [[triglyceride]]s containing heptanoic acid. It is also available through the [[methanolysis]] of natural oils that contain other heptanoate esters.<ref>{{cite journal | last1 = Vonortas | first1 = Andreas | last2 = Papayannakos | first2 = Nikolaos | title = Comparative analysis of biodiesel versus green diesel | journal = WIREs Energy and Environment | date = 2014 | volume = 3 | issue = 1 | pages = 3–23 | doi = 10.1002/wene.78 | bibcode = 2014WIREE...3....3V }}</ref>
==Uses== Methyl heptanoate is primarily used in the flavor and fragrance industry:<ref name=Arctander/><ref name=Burdock>Burdock, George A. (2010). ''Fenaroli's Handbook of Flavor Ingredients'', 6th ed. CRC Press.</ref>
* 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]] in many countries and has the [[FEMA number]] 2705.<ref>{{cite web | url = https://www.femaflavor.org/flavor-library/methyl-heptanoate | website = femaflavor.org | title = 2705: Methyl heptanoate }}</ref>
==Safety== Methyl heptanoate has low acute toxicity; its {{LD50}}s include > 5,000 mg/kg (oral, rat) and > 5,000 mg/kg (dermal, rabbit).<ref>{{cite web | url = https://www.sigmaaldrich.com/US/en/sds/sial/75218 | website = sigmaaldrich.com | title = Safety Data Sheet }}</ref> 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== {{Reflist}}
{{Esters}}
[[Category:Flavors]] [[Category:Perfume ingredients]] [[Category:Fatty acid esters]] [[Category:Methyl esters]]