Tetraiodothyroacetic acid (HCID 65552)

Overview

3,3',5,5'-tetraiodothyroacetic acid is a monocarboxylic acid that is thyroacetic acid carrying four iodo substituents at positions 3, 3', 5 and 5'. It has a role as a thyroid hormone, an apoptosis inducer and a human metabolite. It is an iodophenol, a monocarboxylic acid, an aromatic ether and a 2-halophenol.

Names & identifiers

Preferred name: Tetraiodothyroacetic acid
IUPAC: 2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid
English name: 3,3',5,5'-Tetraiodothyro-acetic acid
Molecular formula: C14H8I4O4
Molecular weight: 747.83

Names & synonyms

Tetrac67-30-13,3',5,5'-TETRAIODOTHYROACETIC ACIDTetraiodothyroacetic acidT4-acetic acidDTXSID5048186PA7UX1FFYQThyroacetic acid, 3,3',5,5'-tetraiodo-3,5-Diiodo-4-(4-hydroxy-3,5-diiodophenoxy)benzeneacetic acidAcide 3,5,3',5'-tetraiodothyroacetiqueDTXCID5028160CHEBI:131194

Show more names

Tetrac, 10 mM in DMSOT4-Acetic acid impuritytetraiodothyroaceticacidLiothyronine EP Impurity DLevothyroxine – Impurity DLevothyroxine EP Impurity DLinagliptin Impurity CD10097Liothyronine Sodium Impurity D3,5,3’,5’-tetraiodothyroacetique

Acetic acid, (4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)-3,5,3',5'-tetraiodothyroacetic acidRefChem:188724200-649-12-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid3,5,3',5'-Tetraiodo Thyroacetic Acid[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetic acid

Database identifiers

CAS: 67-30-1
PubChem CID: 65552
DTXSID: DTXSID5048186
ChEMBL: CHEMBL549748
ChEBI: CHEBI:131194
UNII: PA7UX1FFYQ
EC Number: 200-649-1
Nikkaji: J192.547D

Properties

Computed structural properties

XLogP: 5.2
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 22
Formal charge: 0
Complexity: 373

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section203.1 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5048186]

Physicochemical properties

Melting point: 219 · 219-220 °C (decomp)
Boiling point: 544.8 · 544.8±50.0 °C(Predicted)
Density: 2.727 · 2.727±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: 19.6 · acetone: soluble19.60 - 20.40mg/mL, clear, colorless (or faintly yellow to yellow)
form: powder to crystal
pka: 3.98 · 3.98±0.10(Predicted)
color: White to Yellow to Green
InChI: InChI=1S/C14H8I4O4/c15-8-4-7(5-9(16)13(8)21)22-14-10(17)1-6(2-11(14)18)3-12(19)20/h1-2,4-5,21H,3H2,(H,19,20)
InChIKey: PPJYSSNKSXAVDB-UHFFFAOYSA-N
SMILES: C1(CC(O)=O)=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1
FDA UNII: 7 UX1FFYQ · PA7UX1FFYQ
UNSPSC Code: 12352106 · 12352106
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300
Precautionary statements: 264 · P264-P301+P310
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: T+
Risk Statements: 28 · 28
Safety Statements: 45 · 45
RIDADR: 2811 · UN 2811 6.1/PG 1
WGK Germany: 3 · 3
RTECS: 1585800 · CY1585800
HS Code: 2916.39 · 2916.39.7900
HazardClass: 6.1 · 6.1
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 2 Oral · Acute Tox. 2 Oral
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (300g or 300ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: CY1585800
ridadr: UN 2811 6.1/PG 1
hs_code: 2916.39.7900
risk_code: 28
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+
safety_code: 45
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard statements: H300
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (300g or 300ml)
Hazard Classifications: Acute Tox. 2 Oral
Precautionary statements: P264-P301+P310

Chemistry & industry

Applications · 2 items

UsesThyroid hormone analogue

Uses3,3′,5,5′-Tetraiodothyroacetic acid has been used: as a positive control to study the effects of ioxynil (IOX) diethylstilbestrol (DES) exposure on zebrafish embryosto study its effects on long-term potentiation (LTP) and long-term depression (LTD) in the dentate gyrus in urethane-anesthetized male ratsto determine its influence on the actions of thyroid-stimulating hormonethyroid-stimulating immunoglobulins in orbital fibroblast