Methyl heptanoate

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Methyl heptanoate
Methyl heptanoate v2.svg
Names
IUPAC name
Methyl heptanoate
Other names
Methyl heptylate
Methyl enanthate
Methyl oenanthate
Heptanoic acid, methyl ester
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.118 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-428-8
PubChem CID
UNII
  • Key: XNCNNDVCAUWAIT-UHFFFAOYSA-N
  • InChI=1S/C8H16O2/c1-3-4-5-6-7-8(9)10-2/h3-7H2,1-2H3
  • CCCCCCC(=O)OC
Properties
C8H16O2
Molar mass 144.214 g·mol−1
AppearanceColorless 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]
Insoluble in water [1]
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H315
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):
> 5,000 mg/kg (oral, rat)
> 5,000 mg/kg (dermal, rabbit)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methyl heptanoate is an organic compound with the chemical formula 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 and fragrance industries. [1]

Contents

Properties

Methyl heptanoate is a colorless to pale yellow liquid at room temperature. It has a characteristic orris, 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 . [4]

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 triglycerides containing heptanoic acid. It is also available through the methanolysis of natural oils that contain other heptanoate esters. [5]

Uses

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

It is approved as a flavoring agent in many countries and has the FEMA number 2705. [7]

Safety

Methyl heptanoate has low acute toxicity; its LD50s 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. 1 2 3 4 5 6 7 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ↑ "Methyl hepatanoate". thegoodscentscompany.com.
  3. 1 2 Arctander, Steffen (1969). Perfume and Flavor Chemicals. Montclair, NJ.{{cite book}}: CS1 maint: location missing publisher (link)
  4. ↑ Miyazawa, Mitsuo; Kameoka, Hiromu (1987). "Volatile Flavor Components of ASTRAGALI RADIX ( Astragalus membranaceus Bunge)". Agricultural and Biological Chemistry. 51 (11): 3153–3154. doi:10.1080/00021369.1987.10868496.
  5. ↑ Vonortas, Andreas; Papayannakos, Nikolaos (2014). "Comparative analysis of biodiesel versus green diesel". Wires Energy and Environment. 3 (1): 3–23. Bibcode:2014WIREE...3....3V. doi:10.1002/wene.78.
  6. ↑ Burdock, George A. (2010). Fenaroli's Handbook of Flavor Ingredients, 6th ed. CRC Press.
  7. ↑ "2705: Methyl heptanoate". femaflavor.org.
  8. ↑ "Safety Data Sheet". sigmaaldrich.com.
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