Squalene

CAS# 111-02-4

Squalene

2D Structure

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3D structure

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Squalene

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Chemical Properties of Squalene

Cas No. 111-02-4 SDF Download SDF
PubChem ID 638072 Appearance Oil
Formula C30H50 M.Wt 410.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility DMSO : 16.67 mg/mL (40.59 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
SMILES CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC=C(C)C)C)C)C
Standard InChIKey YYGNTYWPHWGJRM-AAJYLUCBSA-N
Standard InChI 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+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Squalene

The herbs of Catharanthus roseus

Biological Activity of Squalene

DescriptionSqualene, a naturally occurring substance found in plants, animals and humans, is a component of some adjuvants that is added to vaccines to enhance the immune response.Squalene shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene can significantly suppress colonic aberrant crypt foci (ACF) formation and crypt multiplicity strengthens the hypothesis that squalene possesses chemopreventive activity against colon carcinogenesis.
TargetsCOX | STAT | FOXP3 | Nrf2 | SOD | GPx
In vivo

Dietary squalene supplementation improves DSS-induced acute colitis by downregulating p38 MAPK and NFkB signaling pathways.[Pubmed: 25387687]

Mol Nutr Food Res. 2015 Feb;59(2):284-92.

Squalene is a polyunsaturated triterpene, which has exhibited anticancer and antioxidant activities among others. We investigated dietary Squalene supplementation effect on an acute colitis model induced by dextran sulfate sodium (DSS) in C57BL/6 mice.
METHODS AND RESULTS:
Mice were fed from weaning with Squalene at 0.02% and 0.1%. After 4 weeks, mice were exposed to 3% DSS for 5 days developing acute colitis. After DSS removal (5 days), colons were histological and biochemically processed. Our results showed that dietary Squalene treatment exerts anti-inflammatory action in DSS-induced acute colitis. Western blot revealed that Squalene downregulated COX-2 (where COX is cyclooxygenase) and inducible nitric oxide synthase system by inhibition of mitogen-activated protein kinase p38 and the nuclear factor-kappa B signaling pathways, preventing an increase in the cytokines levels. Under our experimental conditions, STAT3 and FOXP3 (where FOXP3 is forkhead box P3) were not modified and the transcriptional regulation of antioxidant and/or detoxifying enzymes, Nrf2 (where Nrf2 is nuclear factor (erythroid-derived 2)-like 2), was reduced in DSS-induced colitis. However, any change could be observed after Squalene supplementation.
CONCLUSIONS:
Squalene was able to improve the oxidative events and returned proinflammatory proteins expression to basal levels probably through p38 mitogen-activated protein kinase and nuclear factor-kappa B signaling pathways. However, supplementary studies are needed in order to provide a basis for developing a new dietary supplementation strategy.

Effect of squalene on cyclophosphamide-induced toxicity.[Pubmed: 16150433]

Clin Chim Acta. 2006 Feb;364(1-2):335-42.

Toxicity due to drugs used for neoplastic disorders is extensively documented. Cyclophosphamide (CYP) is a widely used antineoplastic drug, which could cause toxicity of normal cells due to its toxic metabolites. We evaluated the protective role of Squalene (SQ) in the toxicity induced by cyclophosphamide.
METHODS AND RESULTS:
The activities of serum marker enzymes, clinical chemistry parameters and histopathology studies were done according to the standard procedures in the control and experimental groups of rats. Toxicity of the organs like heart, kidney and liver was evidenced from significant (P<0.05) increases of CK, LDH, AST, ALT, ALP, urea, creatinine and total bilirubin in cyclophosphamide- (150 mg/kg for 2 days) administered rats. Abnormal activities of these enzymes in the organs and serum total protein and cholesterol were also observed. No significant changes were observed in triglycerides in serum. Squalene oral treatment exerted protection towards these organs at a dose of 0.4 ml/day/rat. Histopathological examinations also confirmed the protective efficacy of Squalene.
CONCLUSIONS:
Squalene may be efficacious as a cytoprotectant in cyclophosphamide-induced toxicities.

Protocol of Squalene

Animal Research

Effect of squalene on tissue defense system in isoproterenol-induced myocardial infarction in rats.[Pubmed: 15225664 ]

Chemopreventive effect of squalene on colon cancer.[Pubmed: 9498278]

Carcinogenesis. 1998 Feb;19(2):287-90.

Epidemiologic and laboratory studies suggest a cancer protective effect and/or lack of a tumor promoting effect by dietary olive oil as compared with other types of non-marine oils. Squalene, a constituent of olive oil, and a key intermediate in cholesterol synthesis may be regarded as partially responsible for the beneficial effects of olive oil, which include decreased mortality rates among populations with high olive oil consumption.
METHODS AND RESULTS:
Thus, in this study we have assessed the chemopreventive efficacy of Squalene on azoxymethane (AOM)-induced colonic aberrant crypt foci (ACF). In addition, we measured the effect of Squalene on serum cholesterol levels in the rats. Male F34 rats (5 weeks old) were fed the control diet (modified AIN-76A) or experimental diets containing 1% Squalene or 320 p.p.m. sulindac. Two weeks later, all animals except those in vehicle (normal saline)-treated groups were s.c. injected with AOM (15 mg/kg body wt, once weekly for 2 weeks). At 16 weeks of age, all rats were killed, colons were evaluated for ACF and serum was assayed for the cholesterol levels. As expected, dietary administration of sulindac suppressed ACF development and reduced crypt multiplicity, i.e. number of aberrant crypts/focus. Administration of dietary Squalene inhibited total ACF induction and crypt multiplicity by approximately >46% (P < 0.001). Further, Squalene at a level of 1% did not show any significant effect on serum cholesterol levels.
CONCLUSIONS:
Our finding that Squalene significantly suppresses colonic ACF formation and crypt multiplicity strengthens the hypothesis that Squalene possesses chemopreventive activity against colon carcinogenesis.

Pharmacol Res. 2004 Sep;50(3):231-6.

This study was designed to examine the effects of Squalene on tissue antioxidant status in isoproterenol-induced myocardial infarction in male albino rats.
METHODS AND RESULTS:
Levels of diagnostic marker enzymes [alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH), and creatine phosphokinase (CPK)] in plasma, lipid peroxides, reduced glutathione, and the activities of glutathione-dependent antioxidant enzymes [glutathione peroxidase (GPx) and glutathione-S-transferase (GST)] and antiperoxidative enzymes [catalase (CAT) and superoxide dismutase (SOD)] in the heart tissue of experimental groups of rats were determined. The prior administration of Squalene at 2% level along with feed for 45 days significantly prevented the isoproterenol-induced elevation in the levels of diagnostic marker enzymes in plasma of experimental rats. Squalene also exerted an antioxidant effect against isoproterenol-induced myocardial infarction by blocking the induction of lipid peroxidation. A tendency to prevent the isoproterenol-induced alterations in the level of reduced glutathione and in the activities of glutathione-dependent antioxidant enzymes and antiperoxidative enzymes was also observed.
CONCLUSIONS:
The cardioprotective effect of Squalene might be ascribable to its antioxidant property and membrane stabilizing action.

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Preparing Stock Solutions of Squalene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4349 mL 12.1743 mL 24.3487 mL 48.6973 mL 60.8717 mL
5 mM 0.487 mL 2.4349 mL 4.8697 mL 9.7395 mL 12.1743 mL
10 mM 0.2435 mL 1.2174 mL 2.4349 mL 4.8697 mL 6.0872 mL
50 mM 0.0487 mL 0.2435 mL 0.487 mL 0.9739 mL 1.2174 mL
100 mM 0.0243 mL 0.1217 mL 0.2435 mL 0.487 mL 0.6087 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Squalene

Dietary squalene supplementation improves DSS-induced acute colitis by downregulating p38 MAPK and NFkB signaling pathways.[Pubmed:25387687]

Mol Nutr Food Res. 2015 Feb;59(2):284-92.

SCOPE: Squalene is a polyunsaturated triterpene, which has exhibited anticancer and antioxidant activities among others. We investigated dietary Squalene supplementation effect on an acute colitis model induced by dextran sulfate sodium (DSS) in C57BL/6 mice. METHODS AND RESULTS: Mice were fed from weaning with Squalene at 0.02% and 0.1%. After 4 weeks, mice were exposed to 3% DSS for 5 days developing acute colitis. After DSS removal (5 days), colons were histological and biochemically processed. Our results showed that dietary Squalene treatment exerts anti-inflammatory action in DSS-induced acute colitis. Western blot revealed that Squalene downregulated COX-2 (where COX is cyclooxygenase) and inducible nitric oxide synthase system by inhibition of mitogen-activated protein kinase p38 and the nuclear factor-kappa B signaling pathways, preventing an increase in the cytokines levels. Under our experimental conditions, STAT3 and FOXP3 (where FOXP3 is forkhead box P3) were not modified and the transcriptional regulation of antioxidant and/or detoxifying enzymes, Nrf2 (where Nrf2 is nuclear factor (erythroid-derived 2)-like 2), was reduced in DSS-induced colitis. However, any change could be observed after Squalene supplementation. CONCLUSION: Squalene was able to improve the oxidative events and returned proinflammatory proteins expression to basal levels probably through p38 mitogen-activated protein kinase and nuclear factor-kappa B signaling pathways. However, supplementary studies are needed in order to provide a basis for developing a new dietary supplementation strategy.

Effect of squalene on cyclophosphamide-induced toxicity.[Pubmed:16150433]

Clin Chim Acta. 2006 Feb;364(1-2):335-42.

BACKGROUND: Toxicity due to drugs used for neoplastic disorders is extensively documented. Cyclophosphamide (CYP) is a widely used antineoplastic drug, which could cause toxicity of normal cells due to its toxic metabolites. We evaluated the protective role of Squalene (SQ) in the toxicity induced by cyclophosphamide. METHODS: The activities of serum marker enzymes, clinical chemistry parameters and histopathology studies were done according to the standard procedures in the control and experimental groups of rats. RESULTS: Toxicity of the organs like heart, kidney and liver was evidenced from significant (P<0.05) increases of CK, LDH, AST, ALT, ALP, urea, creatinine and total bilirubin in cyclophosphamide- (150 mg/kg for 2 days) administered rats. Abnormal activities of these enzymes in the organs and serum total protein and cholesterol were also observed. No significant changes were observed in triglycerides in serum. Squalene oral treatment exerted protection towards these organs at a dose of 0.4 ml/day/rat. Histopathological examinations also confirmed the protective efficacy of Squalene. CONCLUSION: Squalene may be efficacious as a cytoprotectant in cyclophosphamide-induced toxicities.

Chemopreventive effect of squalene on colon cancer.[Pubmed:9498278]

Carcinogenesis. 1998 Feb;19(2):287-90.

Epidemiologic and laboratory studies suggest a cancer protective effect and/or lack of a tumor promoting effect by dietary olive oil as compared with other types of non-marine oils. Squalene, a constituent of olive oil, and a key intermediate in cholesterol synthesis may be regarded as partially responsible for the beneficial effects of olive oil, which include decreased mortality rates among populations with high olive oil consumption. Thus, in this study we have assessed the chemopreventive efficacy of Squalene on azoxymethane (AOM)-induced colonic aberrant crypt foci (ACF). In addition, we measured the effect of Squalene on serum cholesterol levels in the rats. Male F34 rats (5 weeks old) were fed the control diet (modified AIN-76A) or experimental diets containing 1% Squalene or 320 p.p.m. sulindac. Two weeks later, all animals except those in vehicle (normal saline)-treated groups were s.c. injected with AOM (15 mg/kg body wt, once weekly for 2 weeks). At 16 weeks of age, all rats were killed, colons were evaluated for ACF and serum was assayed for the cholesterol levels. As expected, dietary administration of sulindac suppressed ACF development and reduced crypt multiplicity, i.e. number of aberrant crypts/focus. Administration of dietary Squalene inhibited total ACF induction and crypt multiplicity by approximately >46% (P < 0.001). Further, Squalene at a level of 1% did not show any significant effect on serum cholesterol levels. Our finding that Squalene significantly suppresses colonic ACF formation and crypt multiplicity strengthens the hypothesis that Squalene possesses chemopreventive activity against colon carcinogenesis.

Effect of squalene on tissue defense system in isoproterenol-induced myocardial infarction in rats.[Pubmed:15225664]

Pharmacol Res. 2004 Sep;50(3):231-6.

This study was designed to examine the effects of Squalene on tissue antioxidant status in isoproterenol-induced myocardial infarction in male albino rats. Levels of diagnostic marker enzymes [alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH), and creatine phosphokinase (CPK)] in plasma, lipid peroxides, reduced glutathione, and the activities of glutathione-dependent antioxidant enzymes [glutathione peroxidase (GPx) and glutathione-S-transferase (GST)] and antiperoxidative enzymes [catalase (CAT) and superoxide dismutase (SOD)] in the heart tissue of experimental groups of rats were determined. The prior administration of Squalene at 2% level along with feed for 45 days significantly prevented the isoproterenol-induced elevation in the levels of diagnostic marker enzymes in plasma of experimental rats. Squalene also exerted an antioxidant effect against isoproterenol-induced myocardial infarction by blocking the induction of lipid peroxidation. A tendency to prevent the isoproterenol-induced alterations in the level of reduced glutathione and in the activities of glutathione-dependent antioxidant enzymes and antiperoxidative enzymes was also observed. The cardioprotective effect of Squalene might be ascribable to its antioxidant property and membrane stabilizing action.

Description

Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity.

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