24880-45-3

Basic information

• Product Name: CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID
• Synonyms: (allz)-7,10,13,16,19-docosapentaenoicacid;13,16,19-docosapentaenoicacid,(allz)-10;CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID;DOCOSAPENTAENOIC ACID;DOCOSA-7Z,10Z,13Z,16Z,19Z-PENTAENOIC ACID;DPA;C22:5 (ALL CIS-7,10,13,16,19) ACID;7,10,13,16,19 (C)-DOCOSAPENTAENOIC ACID
• CAS NO: 24880-45-3
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.5
• Product Categories: Omega 3 fatty acids and derivatives;Polyunsaturated;Unsaturated fatty acids and derivatives
• Mol File: 24880-45-3.mol

Chemical Properties

• Boiling Point: 442.2 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: /
• Density: 0.932 g/cm³
• Vapor Pressure: 4.69E-09mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: −20°C
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID(24880-45-3)
• EPA Substance Registry System: CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID(24880-45-3)

Safety Data

• RIDADR: UN1170 - class 3 - PG 2 - Ethanol
• WGK Germany: 2
• RTECS: JR1320000
• F: 8-10-23
• Hazardous Substances Data: 24880-45-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID is used as an inhibitor of platelet aggregation for preventing blood clot formation. It blocks the cyclooxygenase pathway and stimulates the lipoxygenase pathway, effectively inhibiting platelet aggregation and reducing the risk of cardiovascular events.
Used in Nutritional Supplements:
CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID is used as a nutraceutical ingredient for promoting neurological and ocular health. Its supplementation can help increase the levels of DPA in the human body, which is associated with various health benefits.
Used in Research and Diagnostics:
CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID is used as a Certified Spiking Solution in mass spectrometry-based fatty acid testing applications. It is essential for the assessment of cardiovascular disease risk, fatty acid deficiency, and the detection and quantification of docosapentaenoic acid in nutraceuticals and dietary supplements.
Used in the Food Industry:
CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID is used as an additive in the food industry to enhance the health benefits of products, particularly those rich in omega-3 fatty acids. It can be incorporated into supplements, fortified foods, and other products to improve their nutritional profile and support cardiovascular health.
Used in the Cosmetics Industry:
CIS-7,10,13,16,19-DOCOSA-PENTAENOIC ACID can be used in the cosmetics industry for its potential benefits to skin health, including anti-inflammatory and antioxidant properties. It may be incorporated into skincare products to promote healthy skin and reduce the signs of aging.

InChI:InChI=1/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/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-

Upstream product

• 2734-47-6 (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester 
• 181213-47-8 EPA bromide 
• 86227-47-6 eicosapentaenoic acid ethyl ester 
• 375387-66-9 (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenal 
• 119818-40-5 (7Z,10Z,13Z,16Z,19Z)-ethyl docosa-7,10,13,16,19-pentaenoate 
• 616-29-5 1,3-Diamino-2-hydroxypropane 
• 141-43-5 ethanolamine 
• 66211-46-9 (R)-3-amino-1,2-propanediol 
• 534-03-2 serinol 
• 875288-80-5 methyl (2E,7Z,10Z,13Z,16Z,19Z)-docosa-2,7,10,13,16,19-hexaenoate 
• 10417-94-4 all cis-5,8,11,14,17-eicosapentaenoic acid 
• 61278-21-5 (S)-3-Amino-1,2-propanediol 
• 181213-52-5 ((5Z,8Z,11Z,14Z,17Z)-2-Icosa-5,8,11,14,17-pentaenyl)-malonic acid diethyl ester 
• 164221-12-9 (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol 

Downstream Products

• 1048011-98-8 C₂₈H₄₄O₄ 
• 1288971-25-4 C₂₈H₃₉NO₂ 
• 960593-70-8 docosapentaenoyl chloride 
• 887752-13-8 7,17-dihydroxydocosa-8E,10Z,13Z,15E,19Z-pentaenoic acid 
• 887752-12-7 17-hydroxydocosa-7Z,10Z,13Z,15E,19Z-pentaenoic acid 
• 351317-23-2 (7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-7,10,13,16,19-pentaenamide 
• 1288970-85-3 C₂₈H₄₀N₂O 
• 1288971-58-3 C₂₆H₄₃NO₂ 

Relevant articles and documents

A Convenient Protocol for the Synthesis of Fatty Acid Amides

Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.

COMPOUND, COMPOSITION AND USES THEREOF

The compositions and compounds of formula I, formula II, formula III which includes a salt of polyunsaturated fatty acids in a molecular conjugate with amino acid isoleucine or its polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection administration. Such compositions may be used to treatment of hyperglycemia, metabolic syndrome, diabetes, pre-diabetes, lowering triglycerides or its associated complications.

One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties

A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.

Concise syntheses of three ω-3 polyunsaturated fatty acids

The synthesis of the three ω-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials.

PROCESS FOR PREPARING AND PURIFYING FATTY ACIDS

There is provided a process for purifying a fatty acid, which process comprises reacting a fatty acid with a lithium salt in a first solution and under conditions to allow formation of a precipitate of a lithium salt of the fatty acid; isolating the precipitate; dissolving the precipitate in a second solution followed by separation of the organic and aqueous layers so formed; and evaporating the organic layer to isolate the purified fatty acid. There is also provided a process for increasing the length of a fatty acid, and the use of a lithium salt to purify a fatty acid.

Chemical C2-elongation of polyunsaturated fatty acids

Three fatty acids were synthesized from commercially available α-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block - 2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z,14Z,17Z-eicosatrienoic, 8Z,11Z,14Z,17Z-eicosatetraenoic and 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acids were obtained as colorless oils with >98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds.

Synthesis of C2-elongated polyunsaturated fatty acids

The synthesis by a modified malonic ester procedure of C2-elongated polyunsaturated fatty acids from their natural precursors was described. Using the suggested Scheme 1, (7Z,11Z,14Z)-7,11,14-eicosatrienoic, (8Z,11Z,14Z,17Z)-8,11,14,17-eicosatetraenoic, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic, (8Z,11Z,14Z,17Z)-8,11,14,17-docosatetraenoic, (7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-docosapentaenoic, and (6Z,9Z,12Z,15Z,18Z,21Z)-6,9,12,15,18,21-tetracosahexaenoic acids were synthesized. Their structures were confirmed by GC, UV, and MS data, which coincided with those of natural compounds. The target compounds were shown to be free from by-products, which could result from Z-E isomerization or migration of double bonds. The overall yields of the four-step synthesis of C2-elongated polyenoic acids were 25-30%.