Squalene is a natural organic compound classified as a triterpene.
It plays an essential
role in the biosynthesis of sterols, including cholesterol, in animals and humans. Found in
various plant and animal sources, squalene has gained attention due to its beneficial
properties in cosmetics, health supplements, and even vaccines.
1. Structure of Squalene:
- Chemical Formula: C₃₀H₅₀
- Molecular Structure: Squalene is an acyclic triterpene made up of six isoprene units. It
contains six double bonds, arranged in a linear chain with alternating single and double
bonds, which gives the molecule its characteristic polyunsaturated structure.
- Structural Features:
- It is highly unsaturated and has the general structure of a hydrocarbon chain with double
bonds at specific positions.
- Due to its unsaturation, squalene is prone to oxidation.
- IMPORTANT EXCEPTION:
Squalene consists of six isoprene units, and for the most part, these units are connected in
the usual head-to-tail manner. However, at the central junction, where the two halves of
the molecule meet (between C-12 and C-13), there is a tail-to-tail connection. This tail-to-
tail linkage gives squalene its unique structure and is an important feature for its role as a
biosynthetic precursor to cholesterol and other sterols.
the tail-to-tail bonding at C-12 and C-13 in squalene is due to the specific enzyme-
catalyzed condensation of two farnesyl pyrophosphate molecules, and it is essential for
creating the precursor structure required for sterol biosynthesis.
2. Properties of Squalene:
- Physical State: Squalene is a colorless or pale-yellow oil.
- Solubility: It is insoluble in water but soluble in most organic solvents (e.g., ethanol,
acetone).
- Boiling Point: Around 285°C (545°F) under reduced pressure.
- Chemical Properties:
- Highly unsaturated due to its six double bonds, making it susceptible to oxidation.
- It can undergo hydrogenation to form squalane, a saturated version of squalene that is
more stable and commonly used in cosmetics.
3. Uses of Squalene:
- Cosmetics and Skincare:
- Squalene is widely used in skincare products due to its excellent emollient properties,
providing moisture to the skin without leaving a greasy feel.
- It is also used in anti-aging creams, moisturizers, and sunscreens because of its ability
to reduce water loss, making skin smoother and more hydrated.
- Squalane, its hydrogenated form, is more commonly used in modern cosmetics
because of its enhanced stability against oxidation.
- Health Supplements:
- Squalene is available as a dietary supplement for its antioxidant and anti-inflammatory
properties. It may help support the immune system and improve skin health.
- It is thought to assist in the reduction of cholesterol levels due to its role in cholesterol
biosynthesis.
- Pharmaceuticals and Vaccines:
- Squalene is used as an adjuvant in vaccines, such as in some influenza vaccines, to
enhance the immune response.
- Its adjuvant form, often referred to as MF59, has been used in vaccines to boost the
immune system's response to antigens.
- Potential Therapeutic Uses:
- Some studies suggest that squalene has potential in protecting against oxidative stress,
which is linked to aging and various diseases, including heart disease and cancer.
4. Sources of Squalene:
- Animal Sources:
- Squalene is abundant in shark liver oil, where it was originally discovered. Some shark
species can have liver oil that contains up to 50-70% squalene by weight. Due to ethical
concerns and sustainability issues regarding the harvesting of sharks, alternative sources
are now preferred.
- Plant Sources:
- Squalene is found in olive oil (especially in extra-virgin olive oil), which is a major source
for dietary and industrial uses.
- It is also present in other plant oils such as amaranth seed oil, rice bran oil, wheat
germ oil, and sugarcane.
- Human Body:
- Squalene is naturally produced by the human body as a precursor in the synthesis of
cholesterol. It is found in high concentrations in human sebum (the oil produced by skin
glands), contributing to skin lubrication.
