3,5-Diiodothyronine
Title: 3,5-Diiodothyronine
CAS Registry Number: 534-51-0
CAS Name: O-(4-Hydroxyphenyl)-3,5-diiodotyrosine
Additional Names: 3-[4-(p-hydroxyphenoxy)-3,5-diiodophenyl]alanine
Molecular Formula: C15H13I2NO4
Molecular Weight: 525.08
Percent Composition: C 34.31%, H 2.50%, I 48.34%, N 2.67%, O 12.19%
Literature 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.
 
Derivative Type: DL-Form
Properties: Plates, dec 256-257°.
 
Derivative Type: L(+)-Form
Properties: Crystals, dec 256°. [a]D22 +26° (c = 1.06 in a 1:2 mixture of 1N HCl + alcohol).
Optical Rotation: [a]D22 +26° (c = 1.06 in a 1:2 mixture of 1N HCl + alcohol)
 
Derivative Type: L(+)-Form hydrochloride
Properties: Crystals, mp 235-240°.
Melting point: mp 235-240°
 
Derivative Type: D(-)-Form
Properties: Crystals, dec 256° (Harington), 265° (Elks, Waller). [a]D20 -27.1° (c = 1 in 1N alc HCl:alc, 1:2 by vol).
Optical Rotation: [a]D20 -27.1° (c = 1 in 1N alc HCl:alc, 1:2 by vol)
 
Use: An intermediate in manuf of thyroxine.

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