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HomeProduct name list3,3',5-TRIIODOTHYROACETIC ACID

3,3',5-TRIIODOTHYROACETIC ACID

Synonym(s):4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylacetic acid

  • CAS NO.:51-24-1
  • Empirical Formula: C14H9I3O4
  • Molecular Weight: 621.93
  • MDL number: MFCD00055931
  • EINECS: 200-086-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-14 14:09:35
3,3',5-TRIIODOTHYROACETIC ACID Structural

What is 3,3',5-TRIIODOTHYROACETIC ACID?

Chemical properties

White to Off-White Solid

Originator

Triacana,Ana,Italy,1972

The Uses of 3,3',5-TRIIODOTHYROACETIC ACID

Thyroid hormone analogue

The Uses of 3,3',5-TRIIODOTHYROACETIC ACID

thyroid agent

The Uses of 3,3',5-TRIIODOTHYROACETIC ACID

3,3'',5-Triiodo Thyroacetic Acid (T3-Acetic Acid (USP)) is a thyroid hormone analogue. A potent Thyroxine impurity. Levothyroxine EP Impurity C.

Manufacturing Process

Preparation of 3:5-diiodo-4-(4'-hydroxyphenoxy)phenylacetic acid (diacid): A solution of ethyl 3:5-diiodo-4-(4'-methoxyphenoxy)phenyl acetate (9.5 g) in acetic acid (60 ml) was heated under reflux with hydroiodic acid (SG 1.7, 50 ml) and red phosphorus (0.5 g) for 1 hour. The hot solution was filtered and the filtrate concentrated at 50°C and 15 mm of mercury to above 20 ml. The residue was treated with water (70 ml) containing a little sodium thiosulfate to decolorize the product. The solid was collected by filtration and purified by the method of Harington and Pitt-Rivers [Biochem. J. (1952), Vol. 50, page 438]. Yield 8.36 g (95%). After crystallization from 70% (v/v) acetic acid it melted at 219°C.
A solution of 438 mg of diac in methanol (20 ml) and ammonia solution (SG 0.88; 20 ml) was iodinated at 0°C with 1.8 ml 1 N iodine solution. The product was isolated in almost theoretical yield in a manner similar to that described for tetrac. After crystallization from 50% (v/v) methanol, triac was obtained as colorless needles which melted over the range 65°C to 90°C according to the rate of heating. The molten form resolidified at about 110°C and finally melted at 180°C to 181°C without decomposition. The compound, dried at 25°C/3 mm over silica gel, contains methanol of crystallization.

Therapeutic Function

Thyroid hormone

Properties of 3,3',5-TRIIODOTHYROACETIC ACID

Melting point: 65°; mp 180-183°
Boiling point: 531.6±50.0 °C(Predicted)
Density  2.466±0.06 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
form  Solid
pka 4.02±0.10(Predicted)
color  White to Pale Beige

Safety information for 3,3',5-TRIIODOTHYROACETIC ACID

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

Computed Descriptors for 3,3',5-TRIIODOTHYROACETIC ACID

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