78144-19-1

Basic information

• Product Name: 5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone
• Synonyms: 5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone
• CAS NO: 78144-19-1
• Molecular Formula: C₂₂H₃₁IO₂
• Molecular Weight: 0
• Mol File: 78144-19-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 515.8°C at 760 mmHg
• Flash Point: 265.7°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 9.57E-11mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone(78144-19-1)
• EPA Substance Registry System: 5-iodo-4-hydroxy-7,10,13,16,19-docosapentaenoic acid gamma-lactone(78144-19-1)

Safety Data

• Hazardous Substances Data: 78144-19-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H31IO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22(24)25-21/h3-4,6-7,9-10,12-13,15-16,20-21H,2,5,8,11,14,17-19H2,1H3/b4-3+,7-6+,10-9+,13-12+,16-15+

Upstream product

• 6217-54-5 docosahexaenoic acid 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 

Downstream Products

• 845673-68-9 5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone 
• 121818-29-9 methyl 3-(3-((2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaen-1-yl)oxiran-2-yl)propanoate 
• 6217-54-5 docosahexaenoic acid 
• 845673-74-7 (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid 
• 90906-40-4 (5E,7Z,10Z,13Z,16Z,19Z)-4-Hydroxy-5,7,10,13,16,19-docosahexaenoic acid 
• 51592-59-7 all-cis-3,6,9,12,15-octadecapentaenoic acid 

Relevant articles and documents

Identification of putative metabolites of docosahexaenoic acid as potent PPARγ agonists and antidiabetic agents

We found that putative metabolites of docosahexaenoic acid (DHA) are strong PPARγ activators and potential antidiabetic agents. We designed DHA derivatives based on the crystal structure of PPARγ, synthesized them and evaluated their activities in vitro and in vivo. The efficacy of 5E-4-hydroxy-DHA 2a as a PPARγ activator was about fourfold stronger than that of pioglitazone. Furthermore, the 4-keto derivative (10b) showed antidiabetic activity in animal models without producing undesirable effects such as obesity and hepatotoxicity.

Control Mechanism for Carbon-Chain Length in Polyunsaturated Fatty-Acid Synthases

Polyunsaturated fatty acids (PUFAs) such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) are essential fatty acids. PUFA synthases are composed of three to four subunits and each create a specific PUFA without undesirable byproducts. However, detailed biosynthetic mechanisms for controlling final product profiles have been obscure. Here, the bacterial DHA and EPA synthases were carefully dissected by in vivo and in vitro experiments. In vitro analysis with two KS domains (KSA and KSC) and acyl-acyl carrier protein (ACP) substrates showed that KSA accepted short- to medium-chain substrates while KSC accepted medium- to long-chain substrates. Unexpectedly, condensation from C18 to C20, the last elongation step in EPA biosynthesis, was catalyzed by KSA domains in both EPA and DHA synthases. Conversely, condensation from C20 to C22, the last elongation step for DHA biosynthesis, was catalyzed by the KSC domain in DHA synthase. KSC domains therefore determine the chain lengths.

Construction of a series of intermediates in the β-oxidation pathway from THA to EPA via DHA in free acid form

β-Oxidation of most fatty acids occurs in the mitochondria. However, β-oxidation for ω-3 polyunsaturated fatty acids (PUFAs) is distinct from abundant fatty acids and occurs in the peroxisomes. Since little is known about peroxisomal β-oxidation, here we report the synthesis of proposed intermediates of ω-3 PUFA β-oxidation steps in free fatty acid form having a conjugated double bond, a β-hydroxyl group, a β-olefin and a β-carbonyl group. These fatty acids can serve as authentic samples for biological experiments.