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;
Identifiers
CAS Number	77-93-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL464988 ;
ChemSpider	13850879 ;
ECHA InfoCard	100.000.974
EC Number	201-070-7;
E number	E1505 (additional chemicals)
PubChem CID	6506;
UNII	8Z96QXD6UM ;
CompTox Dashboard (EPA)	DTXSID0040701 ;
	InChI 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 Key: DOOTYTYQINUNNV-UHFFFAOYSA-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;
	SMILES CCOC(=O)CC(CC(=O)OCC)(C(=O)OCC)O;
Properties
Chemical formula	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)
Boiling point	294 °C (561 °F; 567 K) at 1 atm; 235 °C at 150 mmHg
Solubility in water	65 g/L
Magnetic susceptibility (χ)	−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). verify (what is ?) Infobox references

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.

References

^ Triethyl citrate at Sigma-Aldrich
^ 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.
^ ^a ^b Record of Triethyl citrate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ "Triethyl citrate".
^ William J. Stadelman; Owen J. Cotterill (1995). Egg Science and Technology. Haworth Press. ISBN 1-56022-855-5.
^ Pharmaceutical Coatings Bulletin 102-4, morflex.com
^ 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.
^ 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.

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[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.

[itrust-3] 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.

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Names

Preferred IUPAC name Triethyl 2-hydroxypropane-1,2,3-tricarboxylate
Other names Ethyl citrate E1505 Citric acid ethyl ester Triethyl citrate^[2]
Identifiers
CAS Number	77-93-0^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL464988^N
ChemSpider	13850879^N
ECHA InfoCard	100.000.974
EC Number	201-070-7
E number	E1505 (additional chemicals)
PubChem CID	6506
UNII	8Z96QXD6UM^Y
CompTox Dashboard (EPA)	DTXSID0040701
InChI 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
SMILES CCOC(=O)CC(CC(=O)OCC)(C(=O)OCC)O
Properties
Chemical formula	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
Solubility in water	65 g/L^[3]
Magnetic susceptibility (χ)	−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). N verify (what is ^YN ?) Infobox references