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Key Documents

S3626

Sigma-Aldrich

Squalene

≥98%, liquid

Synonym(s):

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

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About This Item

Linear Formula:
[(CH3)2C[=CHCH2CH2C(CH3)]2=CHCH2-]2
CAS Number:
Molecular Weight:
410.72
Beilstein:
1728919
EC Number:
MDL number:
UNSPSC Code:
12352212
PubChem Substance ID:
NACRES:
NA.25

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.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

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