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

Description

Sorbic chloride is an organic compound with the chemical formula C4H6Cl2O2. It is a colorless to pale-yellow liquid with a pungent, irritating odor. Sorbic chloride is commonly used as a chemical intermediate and reagent in various chemical reactions due to its versatile properties.

Uses

Sorbic chloride has a wide range of applications across different industries, primarily as a reactant in the synthesis of various compounds. Here are some of its uses:
Used in Chemical Synthesis:
Sorbic chloride is used as a reactant for the preparation of unsaturated hydroxymethylene diphosphonic acid derivatives by reacting with trimethylsilyl phosphites. This reaction is crucial in the development of new chemical compounds with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, sorbic chloride is used as a reactant in the asymmetrical synthesis of the isoindolinone subunit of the macrocyclic polyketide natural product muironolide A. This synthesis involves a stereoselective intramolecular Diels-Alder cycloaddition, which is essential for the development of new drugs and therapeutic agents.
Used in Cosmetics Industry:
Sorbic chloride is used as a reactant in the preparation of emollient, humectant, and fluorescent α,β-unsaturated thiol esters for long-acting skin applications. These esters are important components in the formulation of various cosmetic products, such as moisturizers, sunscreens, and anti-aging creams, due to their skin-friendly properties.
Used in Asymmetrical Synthesis:
Sorbic chloride is also used in the stereoselective synthesis of enediol carbonates, which are essential for the asymmetrical synthesis of α-acyloxyketones. This process is vital in the development of new chiral compounds with potential applications in the pharmaceutical and agrochemical industries.
Used in Acylation Reactions:
In the field of organic chemistry, sorbic chloride is used as a reactant for the acylation of pyrazoles. This reaction is important for the synthesis of various pyrazole derivatives, which have potential applications as pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

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

Downstream Products

• 100797-52-2 o-tolyl sorbate 
• 1483-88-1 hexa-2,4-dienanilide 
• 1483-88-1 N-phenylsorbamide 
• 69687-90-7 hexadien-(2t,4t)-oic acid-⁽¹⁾-p-tolyl ester 
• 69258-09-9 (2E,4E)-phenyl hexa-2,4-dienoate 
• 62764-13-0 Sorbinsaeure-cyclohexylamid 
• 75378-92-6 N²-(Hexa-2',4'-dienoyl)-N¹,N¹-dimethyl-methacrylamidin 
• 75378-95-9 (2'E)-N²-(Hexa-2',4'-dienoyl)-N¹,N¹-dimethyl-2-phenyl-acrylamidin 
• 134330-12-4 N-(2-methylphenyl)sorbamide 
• 142039-54-1 5-hexa-2,4-dienoic acid benzyl amide 
• 23022-50-6 triethylene glycol monosorbate 
• 61859-45-8 (2E,4E)- 1-(4-morpholinyl)-2,4-hexadien-1-one 
• 134330-11-3 N-(4-methylphenyl)sorbamide 
• 88973-90-4 sorboyloxy-4 benzoate de methyle 

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.

Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.