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| 3,3',5-TRIIODOTHYROACETIC ACID Basic information |
| Product Name: | 3,3',5-TRIIODOTHYROACETIC ACID | | Synonyms: | TIRATRICOL;TRIAC;3,3',5-TRIIODOTHYROACETIC ACID;4-[4-HYDROXY-3-IODOPHENOXY]-3,5-DIIODOPHENYLACETIC ACID;4'-HYDROXY-3,5,3'-TRIIODOPHENOXY-4-PHENYLACETIC ACID;2-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]acetic acid;3,3,5-triiodothyroacetic acid,*free acid;TRIIODOTHYROACETICACID | | CAS: | 51-24-1 | | MF: | C14H9I3O4 | | MW: | 621.93 | | EINECS: | 200-086-1 | | Product Categories: | API;Bioactive Small Molecules;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Aromatics;Drug Analogues;Cell Biology;Chemical Synthesis;Organic Building Blocks;T;Aromatics, Drug Analogues, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;TRIAC;Aromatic Phenylacetic Acids and Derivatives;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 51-24-1.mol |
| 3,3',5-TRIIODOTHYROACETIC ACID Chemical Properties |
| 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 |
| Hazard Codes | Xn | | Risk Statements | 20/21/22 | | Safety Statements | 36 | | WGK Germany | 3 |
| 3,3',5-TRIIODOTHYROACETIC ACID Usage And Synthesis |
| Chemical Properties | White to Off-White Solid | | Originator | Triacana,Ana,Italy,1972 | | Uses | 3,3'',5-Triiodo Thyroacetic Acid (T3-Acetic Acid (USP)) is a thyroid hormone analogue. A potent Thyroxine impurity. Levothyroxine EP Impurity C. | | Uses | Thyroid hormone analogue | | Uses | thyroid agent | | 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 |
| 3,3',5-TRIIODOTHYROACETIC ACID Preparation Products And Raw materials |
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