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Thyroxine: a key hormone molecule in human metabolism Bobbi Parker, Edith James, and Mayra Gillingham
The molecular formula of thyroxine is C15H11I4NO4 and this hormone molecule contains a number of functional groups. This molecule is unusual in that it contains four iodine atoms and two aromatic rings. The official name of thyroxine is tetraiodothyronine (abbreviated as T4). The Lewis structure is shown for thyroxine T4 in Figure 1, with the functional groups each boxed or circled, and labeled. There are 10 functional groups present on the molecule, although only four of the groups are polar. The ball-and-stick model of the molecule is shown in Figure 2 below. The colors of the balls in the model figure are detailed in the caption for Figure 2.
Polarity and water vs. octanol solubility
The thyroxine molecule is considered polar because it contains 4 polar functional groups, mixed into a total of 15 carbon atoms. This ratio matches the typical description of a polar organic molecule, which has no more than 4 C atoms per polar functional group on the molecule. There are nonpolar parts of the thyroxine molecule, namely the two aromatic 6-C rings and the iodine atoms off of these rings (where the C-I bonds are nonpolar covalent bonds). This molecule is considered insoluble in water. It has polar functional groups that can form ‘good’ attractions to water molecules, but not that many groups for the chain length or mass of the molecule. Thyroxine is on the edge of what is usually considered soluble in water for organic molecules, in terms of its ratio of polar functional groups to the number of carbon atoms in the molecule. The molecule also contains 4 iodine atoms, and these large atoms cause the thyroxine molecule to prefer to form attractions (dispersion forces) to itself. The attractions of a thyroxine molecule to smaller sized water molecules, also via dispersion forces, is weaker than the thyroxine-thyroxine attractions. The thyroxine molecule is soluble in the nonpolar solvent 1-octanol. The large molecule here can form ‘decent’ dispersion force attractions to the solvent octanol molecules(which are a mainly nonpolar carbon chain), using its two aromatic rings and their attached iodine atoms. The thyroxine molecule can form hydrogen bonding attractions to water molecules. The carboxylic -OH group, the alcoholic -OH, and the amine group (-NH2) can all accept or donate hydrogen bonding to water molecules. In addition, the O atom of the ether linkage (between the two aromatic rings) and the doubly bonded oxygen atom of the carboxylic group, can each accept hydrogen bonding attractions from water molecules. The carboxylic group has a pKa value of 0.27, meaning that at physiological pH (near 7.4) this group is deprotonated (no H atom on the -COOH group). The alcohol functional group has a pKa of 7.4, which means the -OH is in equilibrium equally with an O- at this position of the 2nd ring in the molecule. The amine group has a pKa of 8.4. This means that at physiological pH the amine nitrogen atom is not often protonated (i.e. charged).
The molecule thyroxine does have a number of different reactivities due to its functional groups. The carboxylic group on the end of the molecule can undergo reactions of the neutralization (reacts with a base) or reduction (to form an aldehyde group, -CHO) types. This carboxylic group is acidic, in that it can donate a proton (H+) in reactions with other base molecules to form products of salt and water. In addition, the carboxylic group could react with a provided alcohol molecule, in a dehydration reaction to form an ester product (RCOOR). The amine functional group is another location that is a reactivity center on the thyroxine molecule. This amine group is basic, in that it can accept an H+ ion in the reaction of the thyroxine molecule with another molecule, such as the acid HCl. This would be a neutralization reaction and would protonate the N atom of the amine group, to form an ionic form of the thyroxine molecule. The amine group on the thyroxine molecule could also react with a provided alcohol molecule, to form an amide where a ‘new’ C-N bond forms (as well as a water molecule as a product). The alcohol functional group (-OH) of the 2nd aromatic ring in the structure of the thyroxine molecule can be part of an oxidation reaction. This would form a ketone group at this position (C=O) of the ring. The ether functional group can be cleaved to form a halogenated product and a 2nd product having an additional alcohol functional group, by reacting thyroxine with HBr molecules for example. But we have not studied this type of reaction in ch112 or the extreme conditions needed for the reaction to occur.
Thyroxine as a drug
Thyroxine is considered a drug and not an essential nutrient. It is needed for proper levels of metabolism in the body but is synthesized in the body (in most people). It is true that thyroxine is essential for good health, but it is not usually required to be taken into the body via a person’s diet. In fact, thyroxine is not found naturally in foods. Essential nutrients are substances that your body can’t make on its own, but that you can take into your body in foods, beverages, or supplements you consume. Examples of essential nutrients include the molecule vitamin C or citric acid, and the minerals iron and calcium. A drug is a molecule taken into the body, that the body does not make, that is used to treat a particular disease that the person has found they have via diagnosis. Thyroxine is considered a drug in that it is a molecule that can be taken by patients whose thyroid gland does not produce any or very little thyroxine. The version of the molecule taken as a drug is called levothyroxine. The structural differences of levothyroxine versus ‘regular’ thyroxine will be detailed in the final report when discussing the physiological role of thyroxine in the metabolism of cells.
Figure 1. A Lewis structure drawing of the molecule thyroxine. The lone pairs of electrons are shown on the drawing as pairs of dots, on specific N, O, or I atoms in the molecule. The functional groups are each boxed or circled and labeled. Polar functional groups have a red-colored box or circle around them in the drawing, while the two aromatic rings have a blue circle drawn around them in the structure.
Figure 2. A ball-and-stick model of the structure of a thyroxine molecule. In the model, the carbon atoms are grey colored spheres, the hydrogen atoms are white-colored, the oxygen atoms are red-colored, the nitrogen atom is blue colored, and the four iodine atoms are shown as purple-colored balls. Double bonds are shown on the aromatic rings, as two rods that connect the two bonded atoms.
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Thyroid Hormones: Functions, Related Diseases and
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