Squalane Chemical Properties

Melting point:

-38 °C (lit.)

Boiling point:

176 °C/0.05 mmHg (lit.)

Density 

0.81 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.452(lit.)

Flash point:

424 °F

storage temp. 

2-8°C

solubility 

chloroform: soluble100mg/mL, clear

color 

Clear Colourless

Water Solubility 

Not miscible or difficult to mix in water.

Merck 

14,8767

BRN 

776019

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

PRAKJMSDJKAYCZ-UHFFFAOYSA-N

LogP

17 at 25℃

CAS DataBase Reference

111-01-3(CAS DataBase Reference)

NIST Chemistry Reference

Tetracosane, 2,6,10,15,19,23-hexamethyl-(111-01-3)

EPA Substance Registry System

Squalane (111-01-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

XB6070000

TSCA 

Yes

HS Code 

29012990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Squalane Usage And Synthesis

Occurrence

Squalane is obtained through the hydrogenation of squalene, and can be used as the oily raw materials of balsam, nutritional emulsion and other basic cosmetics. Squalene was obtained from the liver oil of Centrophorus or other deep-sea shark. Initially, it is the byproduct during the Vitamin A production process from shark liver oil. In recent years, it has been found that unsaponifiable oil of olive oil is rich in squalene, which can be used as the raw material of production of squalane (i.e., fully hydrogenated squalene).

Physical and chemical properties

Refined squalane is a colorless, odorless, inert and transparent oily viscous liquid. Slightly soluble in methanol, ethanol, acetone and glacial acetic acid. It is miscible with benzene, chloroform, carbon tetrachloride, petroleum ether, ether, mineral oil and other animal and vegetable oils. The relative density (15 °C/ 4 ℃) 0.812, refractive index (15 ℃) 1.4530, iodine value 0 ~ 5, saponification value 0 ~ 5, acid value 0 ~ 0.2, freezing point -38 ℃, boiling point 350 ℃. It is stable in the air, but can be slowly oxidized upon the action of sunlight. Sebaceous glands can synthesize squalene. Sebum contain squalene at a content of 1% in children and up to 10% in adult; sebum contains a squalane mass fraction of about 2%. Its permeability, lubricity and breathability is better than other fats, matching well with most cosmetic raw materials.

Squalane application

1. Squalane is widely used as a cosmetic base and finishing cosmetics, precise machinery lubricants, perlite agent of medical ointment and advanced soap.
2. Squalane is a natural product, being inert and non-toxic. It has good affinity to human skin without irritating the skin and causing allergies. It can accelerate the penetration of other actives into the skin. Squalane is a high-grade cosmetic oily raw materials, such as various types of creams and lotions, eyeliners, eyeshadow and conditioner. Cosmetics is mostly natural product extracted directly from cod liver oil. Synthetic products have stimulating effect on the human body, only used as lubricants and UV agents.
3. Squalane is the most commonly used standard non-polar fixative with its polarity being set to zero. Such fixed liquid and component molecules is the dispersion force, mainly used for the separation of general hydrocarbons and non-polar compounds.

Preparation

1. It can be refined directly from the cod liver oil with refinement the first vacuum decompression obtained crude squalane, and then in the nickel catalyst, high temperature, high pressure hydrogenation, remove the double bond part, and then vacuum distillation available.
2. Synthesis method. Take isoprene as raw material; first apply chlorination of isoprene, generating methyl heptanone, followed by dehydrogenation to generate linalool; further apply linalool and geranyl acetone, finally generating squalane.
3. Squalene can be used as raw material with direct hydrogenation to obtain it.
4. Take olive oil as raw material, extract the squalene, and then perform hydrogenation to obtain it.
5. Linalool can react with ethyl acetoacetate to generate 3, 7, 11-trimethyl-dodecane-6, 10-dien-1-yn-3-ol; further use cuprous oxide as a catalyst for oxidation and coupling, hydrogenation to obtain the finished product of squalane.

Cooling Experiment

This product at -55 ℃ without losing its liquidity. Test based on the freezing-point determination method. The thermometer used was a low flow point thermometer, glass bath D, and put into dry ice and acetone for cooling.

Chemical Properties

viscous colourless liquid

Uses

health foods

Uses

Squalane has been used: as solvent in the synthesis of Europium dibenzoylmethide triethylammonium, brightest known triboluminescent (TL) material;as lubricant for fatty acid surfactant films adsorbed on iron oxide surfaces

Uses

Lubricant, transformer oil. Ingredient of watch and chronometer oils. Perfume fixative. In pharmacy and cosmetics as skin lubricant, ingredient of suppositories, carrier of lipid-soluble drugs.

Uses

squalane is an excellent moisturizer and lubricant, it softens and smoothes the skin while also replenishing skin lipids. Its compatibility with skin lipids can be attributed to the fact that human sebum is made up of 25 percent squalane. Squalane has traditionally been obtained by hydrogenation of shark liver oil or other natural oils. Components found in fish oils may reduce skin irritation and allergic responses. It can also be derived from plant sources or synthetically manufactured.

Definition

A saturated hydrocarbon.

General Description

Dielectrophoretic deformation of thin liquid fillm of squalane has been investigated. Microfluidized squalenes are efficient adjuvants, eliciting both humoral and cellular immune responses.

Purification Methods

Purify squalane by fractional distillation in vacuo or evaporative distillation. It is soluble in pet ether, *C6H6, Et2O and CHCl3, slightly soluble in alcohols, Me2CO and AcOH but insoluble in H2O. Small quantities can be purified by TLC as for squalene below. It is used as a marker in GLC and HPLC. [Staudinger & Leupold Helv Chim Acta 15 223 1932, Sax & Stross Anal Chem 29 1700 1951, Mandai et al. Tetrahedron Lett 22 763 1981, Beilstein 1 IV 593.]

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