544-73-0

Basic information

• Product Name: (9E,11E,13E)-9,11,13-octadecatrienoic acid
• Synonyms: (9E,11E,13E)-9,11,13-octadecatrienoic acid;(9E,11E,13E)-9,11,13-Octadecatriensure;Fettsuren, gesttigt und ungesttigt, unverzweigt mit - geradzahliger C-Kette und - C-Zahl >=16 und - einer endstndigen Carboxylgruppe;9,11,13-Octadecatrienoic acid, (E,E,E)-;Ai3-22368;Einecs 208-877-3;(9E, 11E, 13E)-Octadeca-9, 11, 13-trienoic Acid;all-trans-octadeca-9,11,13-trienoic acid
• CAS NO: 544-73-0
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.4296
• EINECS: 208-877-3
• Mol File: 544-73-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 71.5°C
• Boiling Point: 361.24°C (rough estimate)
• Flash Point: 287.4°C
• Appearance: /
• Density: 0.8839
• Refractive Index: 1.5000
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: (9E,11E,13E)-9,11,13-octadecatrienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (9E,11E,13E)-9,11,13-octadecatrienoic acid(544-73-0)
• EPA Substance Registry System: (9E,11E,13E)-9,11,13-octadecatrienoic acid(544-73-0)

Safety Data

• Hazardous Substances Data: 544-73-0(Hazardous Substances Data)

Usage

Description

(9E,11E,13E)-9,11,13-Octadecatrienoic acid, also known as β-ESA, is a conjugated polyunsaturated fatty acid that can be found in plant seed oils and is also produced through the alkaline isomerization of linolenic acid. (9E,11E,13E)-9,11,13-octadecatrienoic acid has been shown to possess biological activities, particularly in the context of cancer cell growth inhibition and modulation of apoptotic pathways.

Uses

Used in Pharmaceutical Industry:
(9E,11E,13E)-9,11,13-Octadecatrienoic acid is used as a potential therapeutic agent for cancer treatment due to its ability to reduce the growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. It induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA, leading to the suppression of cancer cell growth.
Used in Anticancer Applications:
In the field of oncology, (9E,11E,13E)-9,11,13-Octadecatrienoic acid is utilized for its pro-apoptotic effects on cancer cells. It decreases the protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells through the production of reactive oxygen species, thereby contributing to the fight against cancer.
Used in Bacterial Inhibition:
(9E,11E,13E)-9,11,13-Octadecatrienoic acid is also used as an inhibitor of bacterial fatty acid dioxygenase, with a Ki value of 49 nM in vitro. This application is relevant in the development of new antimicrobial agents and understanding the underlying mechanisms of bacterial resistance.

InChI:InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7+,10-9+

Upstream product

• 95168-90-4 octadeca-11t,13t-dien-9-ynoic acid 
• 4175-47-7 methyl α-eleostearate 
• 111699-15-1 (+/-)-t-butyl coriolate 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 110-53-2 1-Bromopentane 
• 16792-04-4 tert-butyl (9Z)-9-octadecenoate 
• 106369-41-9 1-methyl 13-t-butyl (2E,4Z)-2,4-tridecadiene-1,13-dioate 
• 111699-10-6 t-butyl 9-oxononanoate 
• 111699-11-7 t-butyl 9-hydroxy-10-undecynoate 
• 111699-14-0 t-butyl (9Z,11E)-13-oxo-9,11-tridecadienoate 
• 111699-13-9 t-butyl (9Z,11E)-13-hydroxy-9,11-tridecadienoate 
• 111699-12-8 13-t-butyl 1-methyl 3,4-tridecadiene-1,13-dioate 
• 26076-75-5 (E)-hex-1-enyldiisobutylaluminum 
• 96251-48-8 (E,E)-1-chloro-1,3-octadiene 

Downstream Products

• 71599-29-6 octadeca-9,11,13-trienoic acid ethyl ester 
• 822-10-6 (9Z,11E)-methyl octadeca-9,11-dienoate 
• 57-11-4 stearic acid 
• 123-99-9 azelaic acid 
• 131543-46-9 Glyoxal 
• 109-52-4 valeric acid 
• 95699-24-4 3-Butyl-6-<9-carboxy-nonen-(1-cis)-yl-(1)>-4,4,5,5-tetracyan-cyclohexen-(1) 
• 505-48-6 octane-1,8-dioic acid 
• 107-92-6 butyric acid 
• 42021-92-1 (9E,11E,13E)-Octadeca-9,11,13-trienoic acid [2-phenyl-eth-(Z)-ylidene]-hydrazide 
• 42021-93-2 (9E,11E,13E)-Octadeca-9,11,13-trienoic acid [1-methyl-2-phenyl-eth-(Z)-ylidene]-hydrazide 
• 41509-94-8 (9E,11E,13E)-Octadeca-9,11,13-trienoic acid N'-(1-methyl-2-phenyl-ethyl)-hydrazide 
• 48222-46-4 (9E,11E,13E)-Octadeca-9,11,13-trienoic acid N'-phenethyl-hydrazide 

Relevant articles and documents

Stereoselective Synthesis of Octadeacpolyenoic Esters as an Insecticide

Octadecapolyenoic acid derivatives such as (+/-)-t-butyl coriolate, α-eleostearic acid, t-butyl punicate, and t-butyl (9Z,11E)-13-hydroxy-9,11-octadien-15-ynoate were synthesized starting from oleic acid with high stereoselectivity and their insecticidal