Squalene
Systematic name	2,6,10,15,19,23-hexamethyl- 2,6,10,14,18,22-tetracosahexaene
Chemical formula	C30H50
Molecular mass	410.71 g/mol
CAS number	[111-02-4]
Density	0.855 g/cm3
Melting point	-100 °C
Boiling point	285 °C at 25 mmHg
SMILES	CC(C)=CCCC(C)=CCCC(C)=CC CC=C(C)CCC=C(C)CCC=C(C)C
Disclaimer and references

Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Image File history File links This is a lossless scalable vector image. ... Image File history File links Size of this preview: 670 × 600 pixelsFull resolution (1100 × 985 pixel, file size: 164 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Squalene ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article does not cite its references or sources. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Shark liver oil is obtained from sharks caught for food purposes only, living in cold, deep oceans. ... Amarant redirects here. ... Trinomial name Homo sapiens sapiens Linnaeus, 1758 Humans, or human beings, are bipedal primates belonging to the mammalian species Homo sapiens (Latin: wise man or knowing man) in the family Hominidae (the great apes). ... Oil refineries are key to obtaining hydrocarbons; crude oil is processed through several stages to form desirable hydrocarbons, used in fuel and other commercial products. ... Many terpenes are derived from conifer resins, here a pine. ...

Role in steroid synthesis

Squalene is the biochemical precursor to the whole family of steroids. Oxidation (via squalene monooxygenase) of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. In chemistry and biology, Steroids are a type of lipid, characterized by a carbon skeleton with four fused rings. ... Squalene monooxygenase (or squalene epoxidase) is an enzyme which uses NADPH to reduce squalene to 2,3-oxidosqualene (squalene epoxide). ... 2,3-oxidosqualene is an intermediate in the synthesis of lanosterol. ... Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ...

Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene shown. Some intermediates are omitted.

Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Chemical structure of isopentenyl pyrophosphate. ... Structure of dimethyallyl pyrophosphate Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. ... Chemical structure of geranyl pyrophosphate. ...

Shark squalene

Squalene is a low density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the shark's liver, is lighter than water with a specific gravity of 0.855. Environmental and other concerns over shark hunting have motivated its extraction from vegetable sources instead. This article does not cite its references or sources. ... Orders Carcharhiniformes Heterodontiformes Hexanchiformes Lamniformes Orectolobiformes Pristiophoriformes Squaliformes Squatiniformes Symmoriida(extinct) Shark (superorder Selachimorpha) are fish with a full cartilaginous skeleton[1] and a streamlined body. ... The gas bladder (also fish maw, less accurately swim bladder or air bladder) is an internal organ that contributes to the ability of a fish to control its buoyancy, and thus to stay at the current water depth, ascend, or descend without having to waste energy in swimming. ... The liver is an organ present in vertebrates and some other animals. ...

Recently it has become a trend for sharks to be hunted to process their livers for the purpose of making squalene health capsules. However, there is little clinical evidence to prove that, taken internally, squalene does anything to increase an individual's quality of life.

Use as a moisturizer

Squalene is used in cosmetics as a natural, oil-free moisturizer. It also makes up 12% of sebum, a natural product expressed by human sebaceous glands to moisturize hair follicles. Squalene is used in cosmetics as a natural, oil-free moisturizer. It also makes up 12% of sebum, a natural product expressed by human sebaceous glands to moisturize hair follicles. As an alternative to squalene extracted from shark liver and to protect deep water sharks, it has also become available from olive oil making it suitable for ernvironmentally conscious consumers. Squalene has a natural affinity to skin, with a natural spreadability and skin absorption. It penetrates the skin quickly, does not leave your skin greasy and blends well with other oils and vitamins making it a irreplaceable base for high quality cosmetics. The sebaceous glands are glands found in the skin of mammals. ... The sebaceous glands are glands found in the skin of mammals. ...

Biosynthesis

• Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene - by squalene synthase;

Chemical structure of farnesyl pyrophosphate. ... Farnesyl-diphosphate farnesyltransferase (or squalene synthase) is an enzyme which converts farnesyl pyrophosphate into squalene. ... Image File history File links Download high resolution version (1067x152, 5 KB) Taken from Image:Cholesterol-Synthesis-Complete. ...

External links

• Links to external chemical sources