4(Z),7(Z),10(Z),13(Z),16(Z)-Docosapentaenoic acid

• CAS: 25182-74-5
• Catalog Number: ACM25182745-2
• Category: Main Products
• Molecular Weight: 330.5
• Molecular Formula: C22H34O2
• Synonyms: Osbond acid; 4,7,10,13,16-Docosapentaenoic acid all Z
• Appearance: Liquid
• Storage: Freezer
• CNo Chain: C22:5
• Physical State: Liquid

Case Study

Docosapentaenoic Acid as a Lipogenic Gene Regulator in Liver Cells

Drouin, Gaetan, et al. The Journal of nutritional biochemistry 63 (2019): 186-196.

Docosapentaenoic acid (DPA, 22:5n-3) acts as a bioactive n-3 long-chain polyunsaturated fatty acid that down-regulates the transcription factors and enzymes of hepatic fatty acid synthesis, providing a molecular basis for dietary modulation of liver fat metabolism.
Experimental Protocol: Rat FAO hepatoma cells are seeded at 10⁵ cells per well, grown to 70% confluence, and treated with 50 micromolar DPA, eicosapentaenoic acid, docosahexaenoic acid or oleic acid in serum-containing medium for 48 h, with treatments replenished after 24 h; lipogenic gene expression is measured by real-time PCR and protein levels by western blotting. A time-course fatty acid analysis is performed at 0-24 h to track DPA incorporation into phospholipids, and gene expression is repeated after 8 h of incubation.
Performance Evaluation: DPA reduces SREBP-1c mRNA by 96%, HMG-CoA reductase by 93%, and fatty acid synthase by up to 86% relative to oleic acid at 48 h, and lowers ACC-1 and pre-mature SREBP-1 protein by 72% and 71%, respectively. At 8 h, when cell phospholipids contain predominantly DPA with minimal conversion to eicosapentaenoic acid, the lipogenic genes are still suppressed by 54-99%, confirming that the regulatory activity is intrinsic to DPA itself.

Docosapentaenoic Acid as a Dietary n-3 Supplement for Plasma Lipid Modulation

Kaur, Gunveen, et al. Prostaglandins, Leukotrienes and Essential Fatty Acids 85.3-4 (2011): 155-161.

Docosapentaenoic acid (DPA) in ethyl ester form is evaluated as a dietary n-3 polyunsaturated fatty acid supplement whose nutritional intake modulates plasma lipid parameters and tissue fatty acid composition, with effects compared against eicosapentaenoic acid and docosahexaenoic acid.
Experimental Protocol: Thirty-two healthy rats are fed from weaning for 6 weeks with semi-synthetic isoenergetic diets supplemented or not with 1% of total lipids as purified DPA, EPA or DHA ethyl esters of above 99% purity; plasma lipids, antioxidant status and enzyme activities are measured by enzymatic assays, and the fatty acid composition of liver, heart, lung, spleen, kidney, red blood cells and immune cells is determined by gas chromatography-mass spectrometry. Feces are collected for three days to estimate digestibility.
Performance Evaluation: DPA supplementation is the only treatment that decreases plasma triglycerides, total cholesterol, non-HDL cholesterol, cholesterol esters and the total-to-HDL cholesterol ratio relative to control, while all three supplements raise total antioxidant status and superoxide dismutase activity. DPA increases liver docosahexaenoic acid content to the same level as DHA feeding, is retroconverted to EPA in the liver (38.5%) and kidney (68.6%), and shows more than 95% digestibility of the supplemented fatty acid.

Custom Q&A

What is the molecular formula of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The molecular formula is C22H34O2.

What are some synonyms for (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

Some synonyms are Osbond acid, all-cis-4,7,10,13,16-Docosapentaenoic acid, and Docosapentaenoic acid (22n-6).

What is the molecular weight of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The molecular weight is 330.5 g/mol.

What is the role of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

It has a role as a Daphnia tenebrosa metabolite, a human metabolite, and an algal metabolite.

What is the IUPAC name of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The IUPAC name is (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid.

What is the InChI of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The InChI is InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-.

What is the InChIKey of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The InChIKey is AVKOENOBFIYBSA-WMPRHZDHSA-N.

What are the CAS numbers associated with (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid?

The CAS numbers are 25182-74-5 and 25448-00-4.

How many hydrogen bond donor count does (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid have?

It has 1 hydrogen bond donor count.

How many rotatable bond count does (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid have?

It has 15 rotatable bond count.