3191. 3,5-Diiodothyronine

Nomenclature

CAS number: 534-51-0
O-(4-Hydroxyphenyl)-3,5-diiodotyrosine; 3-[4-(p-hydroxyphenoxy)-3,5-diiodophenyl]alanine.
C15H13I2NO4; mol wt 525.08.
C 34.31%, H 2.50%, I 48.34%, N 2.67%, O 12.19%.

Description and references

Prepn of dl-form: Harington, McCartney, Biochem. J. 21, 852 (1927); Borrows et al., J. Chem. Soc. 1949, Suppl. Issue No. 1, S199, S204; Siedel et al., US 2894977 (1959 to Hoechst). Prepn of l(+)-form: Harington, Biochem. J. 22, 1429 (1928); Chambers et al., J. Chem. Soc. 1949, 3424; Hillmann, US 2886592 (1959); as the hydrochloride: Anthony, US 2950315 (1960 to Baxter); Meltzer, US 3102136 (1963 to Warner-Lambert). Prepn of d(-)-form: Harington, loc. cit.; Elks, Waller, J. Chem. Soc. 1952, 2366.

Chemical structure

Derivative

dl-Form.

Properties

Plates, dec 256-257°.

Derivative

l(+)-Form.

Properties

Crystals, dec 256°. [α]D22 +26° (c = 1.06 in a 1:2 mixture of 1N HCl + alcohol).

Derivative

l(+)-Form hydrochloride.

Properties

Crystals, mp 235-240°.

Derivative

d(-)-Form.

Properties

Crystals, dec 256° (Harington), 265° (Elks, Waller). [α]D20 -27.1° (c = 1 in 1N alc HCl:alc, 1:2 by vol).

Use

An intermediate in manuf of thyroxine.