NP-MRD: Showing NP-Card for Triethyl citrate (NP0000038)

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Record Information

Version

2.0

Created at

2012-09-11 19:04:02 UTC

Updated at

2024-09-03 04:22:51 UTC

NP-MRD ID

NP0000038

Natural Product DOI

https://doi.org/10.57994/3001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triethyl citrate

Description

Triethyl citrate is used in foods as a flavouring agent, solvent and surface-active agent Triethyl citrate is an ester of citric acid. It is a colorless, odorless liquid used as a food additive (E number E1505) to stabilize foams, especially as whipping aid for egg white. In pharmaceutical coatings and plastics

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900312D          

 19 18  0  0  0  0            999 V2000
    0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  1  0  0  0  0
 18  5  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
DOOTYTYQINUNNV-UHFFFAOYSA-N

> <FORMULA>
C12H20O7

> <MOLECULAR_WEIGHT>
276.283

> <EXACT_MASS>
276.120902994

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.830255089552697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3-triethyl 2-hydroxypropane-1,2,3-tricarboxylate

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.18541857999999972

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.68953824530732

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.818970937517243

> <JCHEM_PKA_STRONGEST_BASIC>
-4.190181588347824

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
64.177

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triethyl citrate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.461   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1   17                                                       
CONECT    5    2   18                                                       
CONECT    6    3   19                                                       
CONECT    7    9   12                                                       
CONECT    8   10   12                                                       
CONECT    9    7   13   17                                                  
CONECT   10    8   14   18                                                  
CONECT   11   12   15   19                                                  
CONECT   12    7    8   11   16                                             
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17    4    9                                                       
CONECT   18    5   10                                                       
CONECT   19    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Triethyl citric acid	Generator
e1505	HMDB
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester	HMDB
2-Hydroxy-1,2,3-propanetricarboxylic acid, triethyl ester	HMDB
Citric acid, triethyl ester	HMDB
Citroflex 2	HMDB
Crodamol TC	HMDB
Ethyl citrate	HMDB
Ethyl citrate, citric acid triethyl ester	HMDB
Eudraflex	HMDB
FEMA 3083	HMDB
Hydagen c.a.t	HMDB
Hydragen cat	HMDB
TEC	HMDB
Triaethylcitrat	HMDB
Triethyl 2-hydroxy-1,2,3-propanetricarboxylate	HMDB
Triethyl citrate (NF)	HMDB
Triethylester kyseliny citronove	HMDB
Uniflex tec	HMDB
Uniplex 80	HMDB

Chemical Formula

C₁₂H₂₀O₇

Average Mass

276.2830 Da

Monoisotopic Mass

276.12090 Da

IUPAC Name

1,2,3-triethyl 2-hydroxypropane-1,2,3-tricarboxylate

Traditional Name

triethyl citrate

CAS Registry Number

77-93-0

SMILES

CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC

InChI Identifier

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

InChI Key

DOOTYTYQINUNNV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	65 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	10.7 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.19	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.82	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	64.18 m³·mol⁻¹	ChemAxon
Polarizability	27.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034263

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012587

KNApSAcK ID

Not Available

Chemspider ID

13850879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triethyl citrate

METLIN ID

Not Available

PubChem Compound

6506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Triethyl citrate (NP0000038)

MOL for NP0000038 (Triethyl citrate)

3D MOL for NP0000038 (Triethyl citrate)

3D SDF for NP0000038 (Triethyl citrate)

3D-SDF for NP0000038 (Triethyl citrate)

PDB for NP0000038 (Triethyl citrate)

3D PDB for NP0000038 (Triethyl citrate)

SMILES for NP0000038 (Triethyl citrate)

INCHI for NP0000038 (Triethyl citrate)

Structure for NP0000038 (Triethyl citrate)

3D Structure for NP0000038 (Triethyl citrate)