What is squalene



Structural formula
General
Surname Squalene
other names

2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene

Molecular formula C.30H50
CAS number 111-02-4
Brief description colorless liquid
properties
Molar mass 410.71 g mol−1
Physical state liquid
density 0.86 g cm−3[1]
Melting point −75 ° C[1]
boiling point 275 ° C [1]
solubility

easily soluble in gasoline and alcohol; only very poorly soluble in water (

safety instructions
MAK

no MAK

WGK 2[1]
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions.

Squalene (spoken: Squalén) (C30H50) is an organic molecule, a triterpene, which is produced by all higher organisms. This substance also plays a role in the human metabolism.

history

Squalene was founded in 1906 by Dr. Mitsumaru Tsujimoto discovered and isolated as a molecule. He named it after Squalus, Latin for shark. Squalene was discovered in high concentrations in extracts of shark liver oil. Systematic medical research was only introduced in 1930 by Dr. Keijiro Kogami from Tokyo Imperial University. During this research, it was discovered that the sharks did not develop tumors and had immunity to cancer.

In 1936, the Nobel Prize winner Dr. Paul Karrer explored the biochemical structure of squalene for the first time. Later, with the discovery that squalene is also found in the human sebum as a precursor to cholesterol, interest focused primarily on dermatology and the anti-carcinogenic effects of squalene.

Sources of Squalene

Squalene is widespread in nature and can also be found in various foods. In humans it is one of the intermediate stages in cholesterol biosynthesis.

Squalene is found in high concentrations in the liver of some species of shark, such as the liver of the barbary shark, which is widespread on all oceans (40-90%). It is also found in olive oil (0.1-0.7%) and also in other vegetable oils such as wheat germ oil or rice oil (below 0.03%).

Classification

Squalene is an antioxidant and one of the isoprenoids. Unlike other antioxidants, squalene can be stored in higher concentrations in the body. For example, lycopene and ubiquinone cannot be stored in the human body at a high level. They have a toxic effect at concentrations of more than 10 µmol per liter. Squalene is non-toxic even at 100 µM / l. Squalene is naturally excreted from the body.

Applications of squalene

Experimental studies have shown that squalene leads to improved immune system performance. This can be explained by Squalen's essential role in the biomembrane protection of immune cells against oxidative stress. By neutralizing excessive free radicals, squalene allows immune cells to function more efficiently without interference.

properties

Squalene lowers the level of cholesterol in the blood (lowers LDL and increases HDL). Laboratory tests have confirmed its cholesterol lowering properties and have also prompted pharmacology to add squalene to statin drugs (drugs that lower cholesterol levels).

Squalene in skin diseases: UV-B radiation is a source of free radicals and potential skin damage such as skin cancer (melanoma), other possible consequences are suppression of the immune system and allergies. Squalene protects the skin from premature aging and efficiently fights the free radicals that are caused by UV radiation from the sun.

biosynthesis

Squalene is synthesized from isopentenyl pyrophosphate through a series of condensation reactions. This initially produces geranyl pyrophosphate, which then condenses with isopentenyl pyrophosphate to form farnesyl pyrophosphate. Geranyltransferase catalyzes all condensations. Two molecules of farnsyl pyrophosphate are finally linked to squalene with consumption of NADPH, which is catalyzed by squalene synthase in the endoplasmic reticulum.

 

function

Squalene is needed for cholesterol synthesis. Squalene is first activated by a monooxygenase with NADPH consumption, squalene epoxide (2,3-oxidosqualene) is formed. This is finally cyclized into lanosterol by the oxidosqualene cyclase. A series of subsequent reactions ultimately creates cholesterol.

See also

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  1. abcdefG Safety data sheet (Merck)
  • Berg / Tymoczko / Stryer: biochemistry, 5th edition, Spektrum Akademischer Verlag GmbH Heidelberg 2003, ISBN 3827413036

Category: Terpenes