All Photos(1)

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:
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

Hazard Classifications

Asp. Tox. 1

Storage Class Code

10 - Combustible liquids

WGK

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

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)
Jeremiah Whittenton et al.
Journal of microencapsulation, 30(1), 55-63 (2012-06-30)
Effective and targeted in vivo delivery of polynucleotide therapeutics is the key for the treatment of many diseases. Asymmetric immunoliposomes can be used as vehicles to deliver polynucleotides effectively because the two leaflets of the bilayer can have different compositions, which
The Palm Oil Miracle, 63-63 (2007)
Thomas B Elliott et al.
International journal of radiation biology, 91(9), 690-702 (2015-05-23)
A combination therapy for combined injury (CI) using a non-specific immunomodulator, synthetic trehalose dicorynomycolate and monophosphoryl lipid A (STDCM-MPL), was evaluated to augment oral antimicrobial agents, levofloxacin (LVX) and amoxicillin (AMX), to eliminate endogenous sepsis and modulate cytokine production. Female
Rainbow trout leucocyte activity: influence on the ectoparasitic monogenean Gyrodactylus derjavini
Buchmann K and Bresciani J
Diseases of Aquatic Organisms, 35(1), 13-22 (1999)

Articles

Dietary Terpenes

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

Cholesterol Biosynthesis

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.

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