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Cholesterol: Structure, Functions, and Properties

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How Cholesterol Is Transported and Its Biological Importance

Cholesterol originated from the Greek words chole, which means bile, stereos, which means solid, and the suffix -ol, which means alcohol. As a sterol, it is an organic compound and a form of lipid. It is also a structural part of the animal cell membrane that all animal cells can biosynthesize. Cholesteryl alcohol and cholesterin are two other cholesterol chemical names. The hydrogen bond donor and acceptor have property values of 1 and 1, respectively, and the rotatable bond count is 5.


Cholesterol is also a precursor for steroid hormones, bile acid, and vitamin D biosynthesis. Cholesterol is the most common sterol produced by all animals. Hepatic cells are the ones that generate the most in the vertebrates. With the exception of Mycoplasma, which needs cholesterol for growth, it is not present in prokaryotes (bacteria and archaea). This article will study cholesterol formula, cholesterol chemical name, Cholesterol Structure, properties of cholesterol, and cholesterol structure and function. 

Cholesterol Structure

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Properties of Cholesterol

IUPAC name

(3β)-cholest-5-en-3-ol

Cholesterol Molecular Formula/Cholesterol Chemical Formula

C27H46O

Molecular mass

386.664 g/mol

Melting point

148 to 150℃

Boiling Point

360℃

Density 

1.052 g/cm3

Solubility 

Soluble in acetone, benzene, ether, hexane

Solubility in water 

1.8 mg/L at 30℃

Appearance 

White Crystalline Powder


Cholesterol Structure and Function

  1. Membrane 

Cholesterol accounts for roughly 30% of all animal cell membranes. It is required for the construction and maintenance of membranes, as well as the modulation of membrane fluidity over a wide range of physiological temperatures. The hydroxyl groups of cholesterol molecules, as well as the polar heads of membrane phospholipids and sphingolipids, interact with water molecules surrounding the membrane, while the bulky steroid and hydrocarbon chains, as well as the nonpolar fatty-acid chains of the other lipids, are embedded in the membrane. Cholesterol enhances membrane packing by interacting with phospholipid fatty-acid chains, altering membrane fluidity, and maintaining membrane integrity so that animal cells do not need to erect cell walls (like plants and most bacteria). Animal cells can change shape and animals can move because the membrane is stable and strong without being rigid.

  1. Gates

Cholesterol plays a role in intracellular transport, cell signalling, and nerve conduction within the cell membrane. Cholesterol is needed for caveolae-dependent and clathrin-dependent endocytosis, as well as the structure and function of invaginated caveolae and clathrin-coated pits. Cholesterol controls the biological process of substrate presentation as well as the enzymes that use substrate presentation to activate themselves. (PLD2) is a well-known example of an enzyme that is activated by the presence of a substrate.

  1. Signalling

Cholesterol plays a role in cell signaling by assisting in the development of lipid rafts in the plasma membrane, which carry receptor proteins together with high concentrations of second messenger molecules. Cholesterol and phospholipids, both electrical insulators, can help speed up the propagation of electrical impulses along with nerve tissue in multiple layers. A myelin sheath, which is rich in cholesterol since it is derived from compacted layers of Schwann cell membrane, provides protection for many neuron fibres, allowing for more effective impulse conduction. Multiple sclerosis is thought to be caused by demyelination (the failure of some of these Schwann cells).

  1. Chemical Precursor

Cholesterol is a precursor molecule for many biochemical processes within cells. It is the precursor molecule for the synthesis of vitamin D and all steroid hormones, including the adrenal gland hormones cortisol and aldosterone, as well as the sex hormones progesterone, estrogens, and testosterone, and their equivalents, in the calcium metabolism.

  1. Metabolism

In the body, cholesterol is recycled. The liver converts cholesterol into biliary fluids, which are then processed in the gallbladder, which then excretes them into the digestive tract in a non-esterified form (via bile). Approximately half of the cholesterol excreted is reabsorbed into the bloodstream through the small intestine.


Transportation of Cholesterol

Cholesterol is only slightly soluble in water as an isolated molecule, making it hydrophilic. As a result, it dissolves in blood at very low concentrations. Cholesterol is packaged inside lipoproteins, complex discoidal particles with external amphiphilic proteins and lipids, whose outward-facing surfaces are water-soluble and inward-facing surfaces are lipid-soluble, in order to be transported effectively. This causes it to emulsify and pass through the bloodstream. Since unbound cholesterol is amphipathic, it is transported along with phospholipids and proteins in the monolayer surface of the lipoprotein particle. Cholesterol esters attached to fatty acids, on the other hand, are transported along with triglyceride within the lipoprotein.


Did You Know?

According to the lipid theory, high blood cholesterol levels cause atherosclerosis, which can lead to heart attacks, strokes, and peripheral artery disease. Higher blood LDL – especially higher LDL concentrations and smaller LDL particle size – contributes more to this process than the cholesterol content of HDL particles, so LDL particles are often referred to as "poor cholesterol." High levels of functional HDL, which can extract cholesterol from cells and atheromas, provide safety and are referred to as "healthy cholesterol" by the general public. These equilibriums are often determined by genetics, but they can be influenced by body structure, drugs, diet, and other factors.

FAQs on Cholesterol: Structure, Functions, and Properties

1. What is cholesterol and what is its chemical classification?

Cholesterol is an organic molecule classified as a sterol, which is a specific type of lipid. It is a waxy, fat-like substance essential for the normal functioning of all animal cells. From a chemical standpoint, it belongs to the steroid family due to its core structure and serves as a vital biomolecule in numerous biological pathways.

2. What is the basic chemical structure of cholesterol?

The structure of cholesterol is defined by a steroid nucleus, which comprises four fused hydrocarbon rings (labelled A, B, C, and D). This core is known as a cyclopentanoperhydrophenanthrene ring system. Key features attached to this ring system include a hydroxyl (-OH) group at carbon-3, a double bond between carbon-5 and carbon-6, and a branched eight-carbon side chain at carbon-17.

3. What are the primary functions of cholesterol in the human body?

Cholesterol has several crucial functions that are fundamental to human health. Its main roles include:

  • Cell Membrane Integrity: It is a critical component of the cell membrane, where it helps regulate membrane fluidity and stability.
  • Precursor Molecule: It is the starting material for the biosynthesis of several important molecules, including steroid hormones (like estrogen and testosterone), bile acids for digestion, and Vitamin D.
  • Nerve Insulation: It plays a part in forming the myelin sheath that surrounds nerve cells, which is essential for proper nerve signal transmission.

4. How does the structure of cholesterol contribute to its role in the cell membrane?

Cholesterol's unique, amphipathic structure allows it to perform its specific function within the cell membrane's phospholipid bilayer. The rigid, planar steroid ring structure fits between the fatty acid chains of the phospholipids, immobilising them and reducing the membrane's fluidity. Its small, polar hydroxyl (-OH) group orients towards the polar heads of the phospholipids, while the non-polar hydrocarbon tail points inwards, anchoring it within the membrane and enhancing its stability.

5. What is the chemical difference between LDL and HDL in relation to cholesterol?

The terms LDL (“bad cholesterol”) and HDL (“good cholesterol”) do not refer to different types of cholesterol molecules but to the lipoprotein complexes that transport it through the blood. The primary chemical difference is their composition and density:

  • LDL (Low-Density Lipoprotein): Contains a higher percentage of lipids (including cholesterol) and a lower percentage of protein, making it less dense. Its function is to transport cholesterol to the body's cells.
  • HDL (High-Density Lipoprotein): Contains a lower percentage of lipids and a higher percentage of protein, making it denser. Its function is to remove excess cholesterol from the cells and transport it back to the liver.

6. Why is cholesterol classified as a steroid but not a hormone?

Cholesterol is classified as a steroid because its chemical structure is built upon the characteristic four-ring steroid nucleus. However, it is not a hormone itself; rather, it is a precursor to steroid hormones. Hormones are signalling molecules that are secreted by glands to trigger responses in target cells. While cholesterol is the raw material used to synthesise hormones like cortisol and testosterone, it does not have a signalling function of its own.

7. What important biomolecules are synthesised using cholesterol as a precursor?

As per the CBSE Class 12 syllabus, the body utilises cholesterol as a starting point to synthesise several classes of vital biomolecules. These include:

  • Steroid Hormones: This broad category includes sex hormones (e.g., androgens and estrogens) and corticosteroids (e.g., glucocorticoids and mineralocorticoids).
  • Bile Acids: Such as cholic acid, which are synthesised in the liver and are essential for emulsifying fats during digestion.
  • Vitamin D: A cholesterol derivative in the skin is converted to Vitamin D upon exposure to sunlight.

8. How is cholesterol chemically related to the synthesis of Vitamin D?

The chemical link between cholesterol and Vitamin D is through a precursor molecule called 7-dehydrocholesterol, which is an intermediate in cholesterol synthesis. When the skin is exposed to ultraviolet (UVB) light, the energy breaks a specific bond in the B-ring of the 7-dehydrocholesterol molecule. This photochemical reaction transforms it into pre-vitamin D₃, which then spontaneously rearranges (isomerises) with body heat to form the active Vitamin D₃ (cholecalciferol). This illustrates a direct conversion of a sterol into a vitamin.