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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:15 UTC
Update Date2021-10-13 06:39:11 UTC
HMDB IDHMDB0034159
Secondary Accession Numbers
  • HMDB34159
Metabolite Identification
Common NameAcetyl tributyl citrate
DescriptionAcetyl tributyl citrate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Acetyl tributyl citrate is a very faint, sweet, and herbal tasting compound. Based on a literature review a significant number of articles have been published on Acetyl tributyl citrate.
Structure
Data?1563862520
Synonyms
ValueSource
Acetyl tributyl citric acidGenerator
1,2,3-Propanetricarboxylic acid, 2-acetoxy-, tributyl esterHMDB
2-Acetoxy-1,2, 3-propanetricarboxylic acid tributyl esterHMDB
2-Acetoxy-1,2,3-propanetricarboxylic acid tributyl esterHMDB
2-AcetyltributylcitrateHMDB
Acetyl butyl citrateHMDB
Acetyl tri-N-butyl citrateHMDB
Acetylcitric acid, tributyl esterHMDB
Acetyltributyl citrateHMDB
ATBCHMDB
blo-TrolHMDB
Citric acid, tributyl ester, acetateHMDB
Citric acid, tributyl ester, acetate (8ci)HMDB
Citroflex aHMDB
Citroflex a 4HMDB
EstaflexHMDB
FEMA 3080HMDB
O-Acetylcitric acid tributyl esterHMDB
Pfizer citroflex a-4HMDB
Tributyl 2-(acetyloxy)-1,2, 3-propanetricarboxylic acidHMDB
Tributyl 2-(acetyloxy)-1,2,3-propanetricarboxylateHMDB
Tributyl 2-(acetyloxy)-1,2,3-propanetricarboxylic acidHMDB
Tributyl 2-acetoxy-1,2, 3-propanetricarboxylateHMDB
Tributyl 2-acetoxy-1,2,3-propanetricarboxylateHMDB
Tributyl 2-acetoxypropane-1,2,3-tricarboxylateHMDB
Tributyl 2-acetylcitrateHMDB
Tributyl acetyl citrateHMDB
Tributyl acetylcitrateHMDB
Tributyl acetylicitrateHMDB
Tributyl citrate acetateHMDB
Tributyl O-acetylcitrateHMDB
Uniplex 84HMDB
1,2,3-Tributyl 2-(acetyloxy)propane-1,2,3-tricarboxylic acidGenerator
AcetyltributylcitrateMeSH
ATBC plasticizerMeSH
Acetyl tributyl citrateMeSH
Chemical FormulaC20H34O8
Average Molecular Weight402.4792
Monoisotopic Molecular Weight402.225368064
IUPAC Name1,2,3-tributyl 2-(acetyloxy)propane-1,2,3-tricarboxylate
Traditional Nameacetyl tributyl citrate
CAS Registry Number77-90-7
SMILES
CCCCOC(=O)CC(CC(=O)OCCCC)(OC(C)=O)C(=O)OCCCC
InChI Identifier
InChI=1S/C20H34O8/c1-5-8-11-25-17(22)14-20(28-16(4)21,19(24)27-13-10-7-3)15-18(23)26-12-9-6-2/h5-15H2,1-4H3
InChI KeyQZCLKYGREBVARF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling Point172.00 to 173.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility0.005 mg/mLNot Available
LogP5.227 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0071 g/LALOGPS
logP10(3.77) g/LALOGPS
logP10(3.53) g/LChemAxon
logS10(-4.8) g/LALOGPS
pKa (Strongest Acidic)16.18ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area105.2 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity100.7 m³·mol⁻¹ChemAxon
Polarizability44.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.97231661259
DarkChem[M-H]-188.92531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetyl tributyl citrateCCCCOC(=O)CC(CC(=O)OCCCC)(OC(C)=O)C(=O)OCCCC3371.7Standard polar33892256
Acetyl tributyl citrateCCCCOC(=O)CC(CC(=O)OCCCC)(OC(C)=O)C(=O)OCCCC2059.1Standard non polar33892256
Acetyl tributyl citrateCCCCOC(=O)CC(CC(=O)OCCCC)(OC(C)=O)C(=O)OCCCC2436.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetyl tributyl citrate CI-B (Non-derivatized)splash10-0ufr-2159500000-62a9419892ec76844eb82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetyl tributyl citrate CI-B (Non-derivatized)splash10-0ufr-2159500000-62a9419892ec76844eb82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl tributyl citrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9077000000-72ca149c8efcad69872a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl tributyl citrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a73-6930000000-42094b4e6705404355d22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 75V, Positive-QTOFsplash10-014i-9600000000-e0597296cb7bcbf9403d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 90V, Positive-QTOFsplash10-014i-9100000000-c6a22af88a26dfcaf7ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 45V, Positive-QTOFsplash10-004i-0900000000-de22d8d1dbd80d60b4662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 60V, Positive-QTOFsplash10-004i-3900000000-89659d8da8fccf4168602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 30V, Positive-QTOFsplash10-0570-0900000000-7c9683615ce42b8ff8902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl tributyl citrate 15V, Positive-QTOFsplash10-05n0-0930000000-826c372828693a29286b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 10V, Positive-QTOFsplash10-0zfr-4059500000-798fcf70aba58bb2783f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 20V, Positive-QTOFsplash10-0a4i-9253000000-1deb6d64aac0b04dda2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 40V, Positive-QTOFsplash10-0a4i-8092000000-063f4476a3f7507b2a1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 10V, Negative-QTOFsplash10-0zfr-4098400000-e399f7dc6162f68c3eb42016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 20V, Negative-QTOFsplash10-0abj-6097000000-c629137094d887c98c292016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 40V, Negative-QTOFsplash10-0a4i-9141000000-412bf91a7d7802f7caa92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 10V, Negative-QTOFsplash10-0zfr-3039700000-3d02bf6a4a294be40a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 20V, Negative-QTOFsplash10-052r-2194100000-b84e7f2ac3226a0478f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 40V, Negative-QTOFsplash10-0a4l-9140000000-a7a0ec422b86b2f8ee172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 10V, Positive-QTOFsplash10-0udi-0028900000-a147d15fdb812b87b8702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 20V, Positive-QTOFsplash10-006x-2094000000-3843554a80713327eb342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl tributyl citrate 40V, Positive-QTOFsplash10-0a4i-9010000000-5035856fb0d638d6e62c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012444
KNApSAcK IDNot Available
Chemspider ID6259
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetyl tributyl citrate
METLIN IDNot Available
PubChem Compound6505
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .