2614-88-2

Basic information

• Product Name: Sorbic chloride
• Synonyms: Sorbic chloride;(2E,4E)-hexa-2,4-dienoyl chloride;(2E,4E)-2,4-Hexadienoyl chloride;(E,E)-2,4-Hexadienoyl chloride;Sorbic acid chloride;trans,trans-Hexa-2,4-dienoyl chloride
• CAS NO: 2614-88-2
• Molecular Formula: C₆H₇ClO
• Molecular Weight: 130.57218
• Mol File: 2614-88-2.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 169.4°C (rough estimate)
• Appearance: /
• Density: 1.0666
• Refractive Index: 1.5545
• BRN: 969473
• CAS DataBase Reference: Sorbic chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Sorbic chloride(2614-88-2)
• EPA Substance Registry System: Sorbic chloride(2614-88-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 2614-88-2(Hazardous Substances Data)

Usage

Uses

Reactant for:Preparation of unsaturated hydroxymethylene diphosphonic acid derivatives by reaction of trimethylsilyl phosphitesAsymmetrical synthesis of the isoindolinone subunit of the macrocyclic poylketide natural product muironolide A via stereoselective intramolecular Diels-Alder cycloadditionPreparation of emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applicationsStereoselective synthesis of enediol carbonates for use in the asymmetrical synthesis of α-acyloxyketonesAcylation of pyrazoles

Upstream product

• 110-44-1 sorbic Acid 
• 53138-73-1 (2E)-tert-butyl hexa-2,4-dienoate 
• 110-44-1 hexa-2,4-dienoic acid 
• 10385-75-8 parasorbic acid 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 1190-73-4 2-(acetylamino)ethanethiol 

Downstream Products

• 61859-45-8 (2E,4E)- 1-(4-morpholinyl)-2,4-hexadien-1-one 
• 88974-06-5 2-((2E,4E)-Hexa-2,4-dienoylamino)-benzoic acid 
• 16899-71-1 (2E,4E)-cyclohexyl hexa-2,4-dienoate 
• 1051945-98-2 (2E,4E)-((Z)-2-((2-methylallyloxy)carbonyloxy)-2-phenylvinyl) hexa-2,4-dienoate 
• 108595-19-3 1-hexa-2t,4t-dienyloxy-2-methacryloyloxy-ethane 
• 1003863-62-4 (2E,4E)-sorbic acid 2-phenylethyl ester 
• 81530-30-5 5-oxo-7-(prop-1-enyl)-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyrimidine 
• 150492-62-9 N-allyl-N-phenethylsorbamide 
• 35930-77-9 1-(2-hydroxy-5-methyl-phenyl)-hexa-2t,4t-dien-1-one 
• 89062-73-7 6-Methyl-2-((1E,3E)-penta-1,3-dienyl)-4-(phenyl-hydrazono)-5,6-dihydro-4H-pyran-3-carboxylic acid ethyl ester 

Relevant articles and documents

Neutralization-Reionization Study of C6H6O Isomers

Neutralization-reionization (+NR+) mass spectrometry is employed to examine the behavior of C6H6) isomers in the gas phase.Phenol and cyclohexa-2,4-dienone are found not to interconvert following neutralization with mercury of their corresponding cation radicals at 9.9 keV kinetic energy.A very low extent of isomerization is observed following collisional activation of fast C6H6O neutrals with helium.The +NR+ and colisionally activated dissociation spectra, the latter obtained at unit mass resolution, are used to identify these +. isomers.Hexa-1,3,5-trienal is found to cyclize spontaneously to cyclohexa-2,4-dienone during attempted pyrolytic preparation.The thermochemistry of these C6H6O molecules and cation radicals is discussed on the basis of experimental data and MNDO calculations.

Photoinitiated Polymerization of Columnar Stacks of Self-Assembled Trialkyl-1,3,5-benzenetricarboxamide Derivatives

A disk-shaped molecule, N-(5-sorbyl-pentyl)-N′,N″ -di(n-octyl)benzene-1,3,5-tricarboxamide (1), has been synthesized and assembled into a columnar stack in cyclohexane. Using a photoinitiated process, we polymerized monomer 1 in its self-assembled state a

Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol

The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti-infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in-depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin-type synthetic precursors, we have developed enantioselective, one-pot chemo-enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)-epoxysorbicillinol.

A convenient trans diastereoselective synthesis of 3-butadienylazetidinones and their Diels-Alder cycloaddition reactions

An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.

Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones

Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different length and saturation and examined their cytotoxic and antioxidant potential. Our findings indicate that the conjugation with FA affects the biological activity of both the original flavonoids. The conjugation of 6-hydroxy-flavanone increased its cytotoxicity towards prostate cancer PC3 cells. The most noticeable effect was found for oleate conjugate. A similar trend was observed for 7-hydroxy-flavone conjugates with the most evident effect for oleate and stearate. The cytotoxic potential of all tested conjugates was not specific towards PC3 because the viability of human keratinocytes HaCaT cells decreased after exposure to all conjugates. Additionally, we showed that esterification of the two flavonoids decreased their antioxidant activity compared to that of the original compounds. Of all the tested compounds, only 6-sorbic flavanone showed a slight increase in antioxidant potential compared to that of the original compound. Our data show that conjugated flavonoids are better absorbed and enhance cytotoxic effects, but the presence of FA lowered the antioxidant potential.

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.