51592-59-7

Basic information

• Product Name: 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)-
• CAS NO: 51592-59-7
• Molecular Formula: C18H26O2
• Molecular Weight: 274.403
• Mol File: 51592-59-7.mol

Chemical Properties

• CAS DataBase Reference: 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)-(51592-59-7)
• EPA Substance Registry System: 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)-(51592-59-7)

Safety Data

• Hazardous Substances Data: 51592-59-7(Hazardous Substances Data)

Usage

Uses

Used in Nutritional Supplements:
3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)is used as a nutritional supplement for its health-promoting properties. It is included in dietary supplements to ensure adequate intake of this essential fatty acid, which cannot be synthesized by the human body and must be obtained through diet or supplementation.
Used in Functional Foods:
In the Functional Foods industry, 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)is used as an ingredient to enhance the health benefits of food products. It is added to various food items, such as fortified oils, margarines, and spreads, to provide consumers with a source of omega-3 fatty acids and their associated health benefits.
Used in Pharmaceutical Applications:
3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)is used in the pharmaceutical industry for the development of drugs targeting various health conditions. Its anti-inflammatory, cardiovascular, and cognitive-enhancing properties make it a valuable component in the formulation of medications aimed at improving overall health and well-being.
Used in Cosmetics and Personal Care Products:
In the Cosmetics and Personal Care industry, 3,6,9,12,15-Octadecapentaenoic acid, (3Z,6Z,9Z,12Z,15Z)is used as an ingredient in skincare and haircare products. Its anti-inflammatory and nourishing properties contribute to the health and appearance of the skin and hair, making it a sought-after component in various cosmetic formulations.

Upstream product

• 121818-29-9 methyl 3-(3-((2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaen-1-yl)oxiran-2-yl)propanoate 
• 78144-19-1 5-[(3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone 
• 6217-54-5 docosahexaenoic acid 
• 36516-74-2 3,6,9,12,15,18-docosahexaenoic acid 
• 137682-11-2 (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal 

Relevant articles and documents

Toxic effects of Gymnodinium cf. mikimotoi unsaturated fatty acids to gametes and embryos of the sea urchin Paracentrotus lividus

The toxicity of the main Gymnodinium cf. mikimotoi polyunsaturated fatty acid, has been investigated using the sea urchin gamete and embryo bioassays. The 18:5n3 fatty acid delays or inhibits first cleavage of Paracentrotus lividus eggs and provokes abnormalities in the embryonic development. These effects were compared with those of other polyunsaturated fatty acids, 18:4n3, 20:5n3 and 22:6n3, which are also present in this alga. A classification of the different fatty acids, based on their effects on sea urchin egg cleavage and the determination of the half inhibiting concentrations (IC50) is proposed. Copyright (C) 1999 Elsevier Science Ltd. The toxicity of the main Gymnodinium cf. mikitomoi polyunsaturated fatty acid, has been investigated using the sea urchin gamete and embryo bioassays. The 18:5n3 fatty acid delays or inhibits first cleavage of Paracentrotus lividus eggs and provokes abnormalities in the embryonic development. These effects were compared with those of other polyunsaturated fatty acids, 18:4n3, 20:5n3 and 22:6n3, which are also present in this alga. A classification of the different fatty acids, based on their effects on sea urchin egg cleavage and the determination of the half inhibiting concentrations (IC50) is proposed.

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.

ALL-CIS-3,6,9,12,15-OCTADECAPENTAENOIC ACID FROM THE UNICELLULAR ALGA GYMNODINIUM KOWALEVSKII

All-cis-3,6,9,12,15-octadecapentaenoic acid (18:5n-3) was isolated from total lipids of the cultivated microalga Gymnodinium kowalevskii.Its structure was confirmed by GC-MS, 1HNMR, IR and synthesis using a modified method of iodolactonization from 22:6n-3. Key Word Index - Gymnodinium kowalevskii; Gymnodiniaceae; unicellular algae; marine lipids; octadecapentaenoic acid; synthesis.