22329-75-5

Basic information

• Product Name: 2,4-Octadienoic acid, (E,E)-
• Synonyms: octa-2t,4t-dienoic acid;(2E,4E)-2,4-octadienoic acid;(E,E)-2,4-Octadienoic acid;Octa-2t,4t-diensaeure;(2E,4E)-octa-2,4-dienoic acid;2E,4E-octadienoic acid
• CAS NO: 22329-75-5
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Mol File: 22329-75-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2,4-Octadienoic acid, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Octadienoic acid, (E,E)-(22329-75-5)
• EPA Substance Registry System: 2,4-Octadienoic acid, (E,E)-(22329-75-5)

Safety Data

• Hazardous Substances Data: 22329-75-5(Hazardous Substances Data)

Usage

General Description

2,4-Octadienoic acid, also known as sorbic acid, is a naturally occurring organic compound commonly used as a food preservative due to its ability to inhibit the growth of mold, yeast, and some bacteria. It is classified as a polyunsaturated fatty acid and is commonly found in fruits like berries and apples, as well as in some cheeses. The compound is generally recognized as safe for consumption at low levels, and is listed as an approved food additive by the FDA. In addition to its use as a preservative, 2,4-Octadienoic acid has also been studied for its potential health benefits, including anti-fungal and anti-inflammatory properties.

Upstream product

• 18776-92-6 (E)-2-(pent-1-en-1-yl)benzoic acid 
• 75785-78-3 ethyl 3-chlorohexenoate 
• 2305-25-1 3-hydroxy-hexanoic acid ethyl ester 
• 141-82-2 malonic acid 
• 1308312-20-0 3-chlorohexanal 
• 6728-26-3 (E)-2-Hexenal 
• 16400-69-4 6-propyl-5,6-dihydro-2H-pyran-2-one 
• 60388-61-6 ethyl (2E,4E)-octa-2,4-dienoate 
• 4071-85-6 trimetylsilylketene 
• 30361-28-5 trans,trans-2,4-octadienal 
• 110-86-1 pyridine 

Downstream Products

• 56904-85-9 (E,E)-octa-2,4-dien-1-ol 
• 107-92-6 butyric acid 
• 1409973-08-5 C₂₀H₂₁NO 
• 1409973-25-6 C₃₁H₄₃NOSi 
• 60388-65-0 deca-4t,6t-dienoic acid 
• 220944-28-5 (4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-octadienyl)-2-oxazolidinone 
• 247146-38-9 C₆₁H₈₂O₁₈ 
• 214827-40-4 (2E,4E)-Octa-2,4-dienoic acid (4S,5S,7R,7aS)-5-(2-benzenesulfonyl-1,1-dimethyl-ethyl)-5-methoxy-2-oxo-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl)-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-4-yl ester 

Relevant articles and documents

Unsaturated carbonyl compounds and their preparation method and application

The invention discloses a unsaturated carbonyl compounds and their preparation method and application. The unsaturated carbonyl compounds of the general formula as the molecular structure of the following formula (I) as shown: The unsaturated carbonyl com

Total synthesis and antibacterial testing of the A54556 cyclic acyldepsipeptides isolated from streptomyces hawaiiensis

The first total synthesis of all six known A54556 acyldepsipeptide (ADEP) antibiotics from Streptomyces hawaiiensis is reported. This family of compounds has a unique mechanism of antibacterial action, acting as activators of caseinolytic protease (ClpP). Assembly of the 16-membered depsipeptide core was accomplished via a pentafluorophenyl ester-based macrolactamization strategy. Late stage amine deprotection was carried out under neutral conditions by employing a mild hydrogenolysis strategy, which avoids the formation of undesired ring-opened depsipeptide side products encountered during deprotection of acid-labile protecting groups. The free amines were found to be significantly more reactive toward late stage amide bond formation as compared to the corresponding ammonium salts, giving final products in excellent yields. A thorough NMR spectroscopic analysis of these compounds was carried out to formally assign the structures and to aid with the spectroscopic assignment of ADEP analogues. The identity of two of the structures was confirmed by comparison with biologically produced samples from S. hawaiiensis. An X-ray crystallographic analysis of an ADEP analogue reveals a conformation similar to that found in cocrystal structures of ADEPs with ClpP protease. The degree of antibacterial activity of the different compounds was evaluated in vitro using MIC assays employing both Gram-positive and Gram-negative strains and a fluorescence-based biochemical assay.

Mining the Cinnabaramide Biosynthetic Pathway to Generate Novel Proteasome Inhibitors

The cinnabaramides and salinosporamides are mixed PKS/NRPS natural products isolated from a terrestrial streptomycete and a marine actinomycete, respectively. They interfere with the proteasome and thus potentially inhibit the growth of cancer cells. The compounds exhibit a γ-lactam-β-lactone bicyclic ring structure attached to a cyclohexenyl unit and a PKS side chain. As a first step towards improving anticancer activity and permitting genetic approaches to novel analogues, we have cloned and characterized the cinnabaramide biosynthetic genes from Streptomyces sp. JS360. In addition to the expected PKS and NRPS genes, the cluster encodes functionalities for the assembly of the hexyl side chain precursor. The corresponding enzymes exhibit relaxed substrate specificities towards a number of synthesized precursors, enabling production of novel chlorinated cinnabaramides. These were isolated and analyzed for activity, revealing that derivatives bearing a chlorine atom in the PKS side chain show higher inhibitory potentials towards the proteasome's proteolytic subunits (especially the trypsin and chymotrypsin units) and higher cytotoxicities towards human tumor cell lines than the parent cinnabaramide A. Although their activities towards the proteasome were weaker than that of salinosporamide A, the cinnabaramides were found to inhibit the growth of various fungi with greater potency. Copyright