S3626

Sigma-Aldrich

Squalene

≥98%, liquid

Synonym(s):
2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
Linear Formula:
[(CH3)2C[=CHCH2CH2C(CH3)]2=CHCH2-]2
CAS Number:
Molecular Weight:
410.72
Beilstein/REAXYS Number:
1728919
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98%

form

liquid

color

light yellow

refractive index

n20/D 1.494 (lit.)

bp

285 °C/25 mmHg (lit.)

mp

−75 °C (lit.)

density

0.858 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)=CCCC(C)=CCCC(C)=CCC\C=C(/C)CCC=C(C)CCC=C(C)C

InChI

1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+

InChI key

YYGNTYWPHWGJRM-AAJYLUCBSA-N

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General description

Squalene is a hydrocarbon containing double bond commonly found in shark liver oil. It is also present in vegetable oils but to a lesser extent.

Application

Squalene has been used:
  • as a standard for lipid identification and quantification
  • in the isolation of macrophages for parasite incubation
  • as a standard for the quantification of squalene in squalene analysis of oil samples

Packaging

1 L in glass bottle
10, 100, 500 mL in glass bottle

Biochem/physiol Actions

Squalene is a biosynthetic precursor to all steroids. It acts as a cytoprotective agent to normal cells exposed to carcinogens and antitumor agents. Squalene helps in equalizing the blood cholesterol levels. It increases the production of HDL (high density lipoprotein) and the excretion of LDL (low density lipoprotein). This helps in reducing the risk of heart disease and protects the less stable body fats from oxidation. It is also used in treating hypercholesterolemia. Squalene is known to improve the efficiency of cholesterol lowering drugs. It also serves as an antioxidant by preventing the effects of free radical. It protects skin from drying and other environmental conditions such as oxidation, ultraviolet rays and pollutants. Squalene is known to promote wound healing.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

hazcat

Asp. Tox. 1

storage_class_code

10 - Combustible liquids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Reduced skin barrier function parallels abnormal stratum corneum lipid organization in patients with lamellar ichthyosis
Lavrijsen APM, et al.
The Journal of Investigative Dermatology, 105(4), 619-624 (1995)
Zih-rou Huang et al.
Acta pharmacologica Sinica, 29(9), 1094-1102 (2008-08-23)
Camptothecin is an anticancer drug that acts against a broad spectrum of tumors. The clinical application of camptothecin is limited by its insolubility, instability, and toxicity problems. The aim of this study was to develop and characterize lipid nanoparticles with...
Influence of the addition of Amaranthus mantegazzianus flour on the nutritional and health properties of pasta
Martinez CS, et al.
Cogent Food & Agriculture, 2(1), 1136097-1136097 (2016)
The Palm Oil Miracle, 63-63 (2007)
Biological importance and applications of squalene and squalane
Advances in Food and Nutrition Research, 65, 223-233 (2012)
Articles
Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.
Read More
Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.
Read More

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