Steroids – Online Organic Chemistry Tutor

Steroids - Online Organic Chemistry Tutor

Steroids are organic compounds composed of 17 carbon atoms with fused rings, three of which are six-membered, and a five-membered ring. It can be obtained from plants as well as animals.

The word steroid comes from sterols. Adrenal hormones, bile acids and cortical hormones are some examples of steroids. 1,2-Cyclopentanophenanthrene is the basic structure present in steroids. If the substance in a steroidal compound changes, a new molecule is produced that may differ in its therapeutic action.

Stereochemistry:

  1. In a steroidal compound, there are six chiral carbons present, so 64 optical isomers are possible. 5, 8, 9, 10, 13 and 14 are asymmetric carbons.
  2. All cyclohexane can exist in two morphological forms: chair and boat. The chair structure is more stable than the boat because of the low angle stress.
  3. The stereoisomer is present at the base of ring A and ring B fused. The fusion of rings can be a and can be cis or trans; Therefore, two isomeric forms can be produced.
  4. The fusion of rings B/C and C/D is trans. This is due to the configuration of 8-beta and 9-alpha hydrogen, 14-alpha hydrogen and carbon 18 methyl.
  5. There is a trans, anti-trans and anti-trans fusion of the rings in 5 alpha cholestane.
  6. 5-beta cholestane consists of A/B rings with cis-fused and cis-syn-trans and antitrans backbones. A student needs to know about the configuration of steroids as these are fundamental units. If they have a hard time figuring this out, they can go through steroid homework help.

Types of Sterols:

  • Zoo Sterol: It is mainly present in animals. Example: cholesterol. It can be found in free form or ester form. The molecular formula of cholesterol is C. Is27h25 It consists of a hydroxyl group, a hydrocarbon tail, and four fused rings. The hydroxyl group is polar; Hence it can easily dissolve in water.

The fused ring system and hydrocarbon tail are hydrophobic. Therefore, cholesterol is considered to be amphipathic as it has both hydrophobic and hydrophilic parts in its structure. Cholesterol can be converted to cholestanol using hydrogen and platinum as catalysts.

  • Sapogenins: These contain steroids and triterpenes, which is why they are called tetracyclic triterpenoids. These are the aglycone portions derived from saponins by enzymatic or acid hydrolysis. They can be identified on the basis of the spirochetal chain present in the structure.

They are derivatives of C-27 cholestane. A spiro compound has two cyclic rings joined by a single atom, and that atom is called a quaternary atom or spiro atom. Diosgenin, strophanthus, and digitalis belong to this category.

  • Cardiac glycoside is a bitter, water-soluble component but insoluble in organic solvents. They are very toxic and odorless amorphous powder. They help in increasing the rhythm, excitability and contractility of the muscles present in the heart.

On enzymatic hydrolysis the glycone and aglycone moieties are produced which are cardinolides and bufadienolides. Cardinolides have a double bond in the lactone ring, with five members attached to the steroidal nucleus at positions 17. Bufedienolides consist of a 6-membered lactone ring with two double bonds attached to the steroidal nucleus at the carbon number 17 alpha position.

  • Sex steroids: This includes estrogen, androgen, and estrogens. Also called gonadocorticoids/gonadal steroids. It is hydrophobic and binds to the hormone receptor present in the cytoplasm. Androgens are produced from cholesterol produced in the testes and adrenal cortex. Testosterone Aldosterone is a naturally stimulating hormone in humans. Detailed explanation on steroid assignment help is given by the experts in this section.

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