Cholesterol (C27H46O), a compound that is sometimes in the news, is a white, waxy solid produced in the liver of every animal, including humans. It is important for giving structure to cell membranes and in producing certain hormones (chemicals that regulate cellular activity in the body, including sex hormones and adrenal hormones). It is a precursor to vitamin D. As such, it is necessary for life, but why is cholesterol the object of attention?

(A) The four-fused-ring steroid skeleton uses letter designations for each ring and the numbering of the carbon atoms. (b) The cholesterol molecule follows this pattern.
(A) The four-fused-ring steroid skeleton uses letter designations for each ring and the numbering of the carbon atoms. (b) The cholesterol molecule follows this pattern.

Cholesterol and Heart Disease

Besides producing cholesterol, we also ingest some whenever we eat meat or other animal-based food products. People who eat such products in large quantities, or whose metabolisms are unable to handle excess amounts, may experience an unhealthy buildup of cholesterol in their blood. Deposits of cholesterol, called plaque, may form on blood vessel walls, eventually blocking the arteries and preventing the delivery of oxygen to body tissues. Heart attacks, strokes, and other circulatory problems can result.

To understand the link between heart disease and cholesterol levels, it is important to understand how cholesterol is transported in the body. Like fats and oils, cholesterol is not soluble in water and therefore cannot be transported in the blood (an aqueous medium) unless they are complexed with proteins that are soluble in water, forming assemblages called lipoproteins. Lipoproteins are classified according to their density, which is dependent on the relative amounts of protein and lipid they contain. Lipids are less dense than proteins, so lipoproteins containing a greater proportion of lipid are less dense than those containing a greater proportion of protein.

A lipoprotein
A lipoprotein

Research on cholesterol and its role in heart disease has focused on serum levels of low-density lipoproteins (LDLs) and high-density lipoproteins (HDLs). One of the most fascinating discoveries is that high levels of HDLs reduce a person’s risk of developing heart disease, whereas high levels of LDLs increase that risk. Thus the serum LDL:HDL ratio is a better predictor of heart disease risk than the overall level of serum cholesterol. Persons who, because of hereditary or dietary factors, have high LDL:HDL ratios in their blood have a higher incidence of heart disease.

How do HDLs reduce the risk of developing heart disease? No one knows for sure, but one role of HDLs appears to be the transport of excess cholesterol to the liver, where it can be metabolized. Therefore, HDLs aid in removing cholesterol from blood and from the smooth muscle cells of the arterial wall.

Dietary modifications and increased physical activity can help lower total cholesterol and improve the LDL:HDL ratio. The average American consumes about 600 mg of cholesterol from animal products each day and also synthesizes approximately 1 g of cholesterol each day, mostly in the liver. The amount of cholesterol synthesized is controlled by the cholesterol level in the blood; when the blood cholesterol level exceeds 150 mg/100 mL, the rate of cholesterol biosynthesis is halved. Hence, if cholesterol is present in the diet, a feedback mechanism suppresses its synthesis in the liver. However, the ratio of suppression is not a 1:1 ratio; the reduction in biosynthesis does not equal the amount of cholesterol ingested. Thus, dietary substitutions of unsaturated fat for saturated fat, as well as a reduction in consumption of trans fatty acids, is recommended to help lower serum cholesterol and the risk of heart disease. Diets that are more heavily plants-based are a health choice since cholesterol does not occur in plants and plants contain more unsaturated fats and less saturated fats. Tests are available to measure cholesterol in the blood, and there are several drugs capable of lowering cholesterol levels.

Cholesterol and the Gallbladder

In addition to heart disease, cholesterol also contributes to the formation of gallstones. Excess cholesterol not metabolized by the body is released from the liver and transported by the blood to the gallbladder. Normally, it stays in solution there until being secreted into the intestine (as a component of bile) to be eliminated. Sometimes, however, cholesterol in the gallbladder precipitates in the form of gallstones. Indeed, the name cholesterol is derived from the Greek chole, meaning “bile,” and stereos, meaning “solid.”


This page is based on “Chemistry 2e” by Paul Flowers, Klaus Theopold, Richard Langley, William R. Robinson, PhDOpenstax which is licensed under CC BY 4.0. Access for free at

This page is based on “The Basics of General, Organic, and Biological Chemistry” by David W Ball, John W Hill, Rhonda J ScottSaylor which is licensed under CC BY-NC-SA 4.0. Access for free at


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