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Merck

S3626

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:
111-02-4
Molecular Weight:
410.72
UNSPSC Code:
12352212
NACRES:
NA.25
PubChem Substance ID:
24899564
EC Number:
203-826-1
Beilstein/REAXYS Number:
1728919
MDL number:
MFCD00008912

Key Documents

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Product Name

Squalene, ≥98%, liquid

InChI key

YYGNTYWPHWGJRM-AAJYLUCBSA-N

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+

SMILES string

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

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

Quality Level

100

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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.

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.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H304

Hazard Classifications

Asp. Tox. 1

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6731
MKCV2132
MKCQ0973
MKCP0452
MKCM5169

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Biological importance and applications of squalene and squalane
Advances in Food and Nutrition Research, 65, 223-233 (2012)
The Palm Oil Miracle, 63-63 (2007)
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)
Joachim Caron et al.
Advanced healthcare materials, 2(1), 172-185 (2012-12-06)
A series of new lipid prodrugs of paclitaxel, which can be formulated as nanoassemblies, are described. These prodrugs which are designed to overcome the limitations due to the systemic toxicity and low water solubility of paclitaxel consist of a squalene
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
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