T3DB: Acetyl tributyl citrate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (5)XML

Targets (5)

Record Information

Version

2.0

Creation Date

2014-09-11 05:20:10 UTC

Update Date

2014-12-24 20:26:58 UTC

Accession Number

T3D4871

Identification

Common Name

Acetyl tributyl citrate

Class

Small Molecule

Description

Acetyl tributyl citrate is a flavouring ingredient and plasticiser used in packaging films for food.

Compound Type

Ester
Ether
Flavouring Agent
Food Additive
Food Toxin
Household Toxin
Metabolite
Organic Compound
Plasticizer
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1,2,3-Propanetricarboxylic acid, 2-acetoxy-, tributyl ester
2-Acetoxy-1,2, 3-propanetricarboxylic acid tributyl ester
2-Acetoxy-1,2,3-propanetricarboxylic acid tributyl ester
2-Acetyltributylcitrate
Acetyl butyl citrate
Acetyl tri-N-butyl citrate
Acetyl tributyl citric acid
Acetylcitric acid, tributyl ester
Acetyltributyl citrate
ATBC
Blo-trol
Citric acid, tributyl ester, acetate
Citric acid, tributyl ester, acetate (8CI)
Citroflex a
Citroflex A 4
Estaflex
FEMA 3080
O-Acetylcitric acid tributyl ester
Pfizer citroflex A-4
Tributyl 2-(acetyloxy)-1,2, 3-propanetricarboxylic acid
Tributyl 2-(acetyloxy)-1,2,3-propanetricarboxylate
Tributyl 2-(acetyloxy)-1,2,3-propanetricarboxylic acid
Tributyl 2-acetoxy-1,2, 3-propanetricarboxylate
Tributyl 2-acetoxy-1,2,3-propanetricarboxylate
Tributyl 2-acetoxypropane-1,2,3-tricarboxylate
Tributyl 2-acetylcitrate
Tributyl acetyl citrate
Tributyl acetylcitrate
Tributyl acetylicitrate
Tributyl citrate acetate
Tributyl O-acetylcitrate
Uniplex 84

Chemical Formula

C₂₀H₃₄O₈

Average Molecular Mass

402.479 g/mol

Monoisotopic Mass

402.225 g/mol

CAS Registry Number

77-90-7

IUPAC Name

1,2,3-tributyl 2-(acetyloxy)propane-1,2,3-tricarboxylate

Traditional Name

acetyl tributyl citrate

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 Key

InChIKey=QZCLKYGREBVARF-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-80 °C
Boiling Point	Not Available
Solubility	0.005 mg/mL
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0071 g/L	ALOGPS
logP	3.77	ALOGPS
logP	3.53	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	16.18	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	100.7 m³·mol⁻¹	ChemAxon
Polarizability	44.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0ufr-2159500000-62a9419892ec76844eb8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0ufr-2159500000-62a9419892ec76844eb8	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9077000000-72ca149c8efcad69872a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-9600000000-e0597296cb7bcbf9403d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9100000000-c6a22af88a26dfcaf7ec	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-0900000000-de22d8d1dbd80d60b466	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-004i-3900000000-89659d8da8fccf416860	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0570-0900000000-7c9683615ce42b8ff890	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-05n0-0930000000-826c372828693a29286b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-4059500000-798fcf70aba58bb2783f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9253000000-1deb6d64aac0b04dda2a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8092000000-063f4476a3f7507b2a1c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-4098400000-e399f7dc6162f68c3eb4	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abj-6097000000-c629137094d887c98c29	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9141000000-412bf91a7d7802f7caa9	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-3039700000-3d02bf6a4a294be40a59	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-2194100000-b84e7f2ac3226a0478f2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9140000000-a7a0ec422b86b2f8ee17	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0028900000-a147d15fdb812b87b870	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-2094000000-3843554a80713327eb34	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9010000000-5035856fb0d638d6e62c	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a73-6930000000-42094b4e6705404355d2	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Acetyl_tributyl_citrate

References

Synthesis Reference

Not Available

MSDS

T3D4871.pdf

General References

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

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Nuclear receptor subfamily 1 group I member 2

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.56 uM	ATG_PXR_TRANS	Attagene
AC50	1.89 uM	ATG_PXRE_CIS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. Cytochrome P450 2C19

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular Weight:: 55930.545 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.82 uM	NVS_ADME_hCYP2C19	Novascreen

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

3. Estrogen receptor

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular Weight:: 66215.45 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.38 uM	OT_ERa_EREGFP_0120	Odyssey Thera

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

4. Vitamin D3 receptor

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
Gene Name:: VDR
Uniprot ID:: P11473
Molecular Weight:: 48288.64 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.68 uM	ATG_VDRE_CIS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

5. Bile acid receptor

General Function:: Zinc ion binding
Specific Function:: Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
Gene Name:: NR1H4
Uniprot ID:: Q96RI1
Molecular Weight:: 55913.915 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.86 uM	OT_SRC1_SRC1FXR_0480	Odyssey Thera

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Acetyl tributyl citrate (T3D4871)

Structure for T3D4871: Acetyl tributyl citrate

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References