Triethyl citrate

Triethyl citrate[1]
Names
Preferred IUPAC name
Triethyl 2-hydroxypropane-1,2,3-tricarboxylate
Other names
  • Ethyl citrate
  • E1505
  • Citric acid ethyl ester
  • Triethyl citrate[2]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.974 Edit this at Wikidata
EC Number
  • 201-070-7
E number E1505 (additional chemicals)
UNII
  • InChI=1S/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3 ☒N
    Key: DOOTYTYQINUNNV-UHFFFAOYSA-N ☒N
  • InChI=1/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3
    Key: DOOTYTYQINUNNV-UHFFFAOYAG
  • CCOC(=O)CC(CC(=O)OCC)(C(=O)OCC)O
Properties
C12H20O7
Molar mass 276.283 g/mol
Appearance Oily liquid
Density 1.137 g/mL at 25 °C
Melting point −55 °C (−67 °F; 218 K)[3]
Boiling point 294 °C (561 °F; 567 K) at 1 atm
235 °C at 150 mmHg
65 g/L[3]
−161.9·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethyl citrate is an ester of citric acid. It is a colorless, odorless liquid used as a food additive, emulsifier and solvent (E number E1505)[4] to stabilize foams, especially as whipping aid for egg white.[5] It is also used in pharmaceutical coatings and plastics.[6]

Triethyl citrate is also used as a plasticizer for polyvinyl chloride (PVC) and similar plastics.[7]

Triethyl citrate has been used as a pseudo-emulsifier in e-cigarette juices.[8] It functions essentially like lecithin used in food products, but with the possibility of vaporization which lecithin does not have.

  1. ^ Triethyl citrate at Sigma-Aldrich
  2. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 747. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ a b Record of Triethyl citrate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ "Triethyl citrate".
  5. ^ William J. Stadelman; Owen J. Cotterill (1995). Egg Science and Technology. Haworth Press. ISBN 1-56022-855-5.
  6. ^ Pharmaceutical Coatings Bulletin 102-4, morflex.com
  7. ^ Hwan-Man Park; Manjusri Misra; Lawrence T. Drzal & Amar K. Mohanty (2004). ""Green" Nanocomposites from Cellulose Acetate Bioplastic and Clay: Effect of Eco-Friendly Triethyl Citrate Plasticizer". Biomacromolecules. 5 (6): 2281–2288. doi:10.1021/bm049690f. PMID 15530043.
  8. ^ Erythropel, Hanno C; Anastas, Paul T; Krishnan-Sarin, Suchitra; O'Malley, Stephanie S; Jordt, Sven Eric; Zimmerman, Julie B (2020-04-27). "Differences in flavourant levels and synthetic coolant use between USA, EU and Canadian Juul products". Tobacco Control. 30 (4): tobaccocontrol–2019–055500. doi:10.1136/tobaccocontrol-2019-055500. ISSN 0964-4563. PMC 7606218. PMID 32341193.