Thiocyanates and Isothiocyanates, Organic

Romanowski, Frank; Klenk, Herbert

doi:10.1002/14356007.a26_749

Cited by 9 publications

(13 citation statements)

References 36 publications

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“…Allyl isothiocyanate (AIT) is a colorless oil that is responsible for the pungent taste of mustard, horseradish, and wasabi. It is slightly soluble in water, but well soluble in most organic solvents [29]. AIT comes from the seeds of black mustard ( Brassica nigra ) or brown Indian mustard ( Brassica juncea ).…”

Section: Discussionmentioning

confidence: 99%

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A novel retinoic acid, catechin hydrate and mustard oil-based emulsion for enhanced cytokine and antibody responses against multiple strains of HIV-1 following mucosal and systemic vaccinations

Vajdy

2011

Vaccine

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Non-replicating protein-or DNA-based antigens generally require immune-enhancing adjuvants and delivery systems. It has been particularly difficult to raise antibodies against gp120 of HIV-1, which constitutes an important approach in HIV vaccine design. While almost all effort in adjuvant research has focused on mimicking the pathogens and the danger signals they engender in the host, relatively little effort has been spent on nutritive approaches. In this study, a new nutritive immune-enhancing delivery system (NIDS) composed of vitamin A, a polyphenolflavonoid catechin hydrate, and mustard oil was tested for its adjuvant effect in immune responses against the gp120 protein of HIV-1 CN54 . Following a combination of two mucosal and two systemic vaccinations of mice, we found significant enhancement of both local and systemic antibodies as well as cytokine responses. These data have important implications for vaccine and adjuvant design against HIV-1 and other pathogens.

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Section: Discussionmentioning

confidence: 99%

“…When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to produce AIT. Known as synthetic mustard oil, AIT can be produced commercially by the reaction of allyl chloride and potassium thiocyanate: CH 2 =CHCH 2 Cl + KSCN → CH 2 =CHCH 2 NCS + KCl [29]. …”

Section: Discussionmentioning

confidence: 99%

A novel retinoic acid, catechin hydrate and mustard oil-based emulsion for enhanced cytokine and antibody responses against multiple strains of HIV-1 following mucosal and systemic vaccinations

Vajdy

2011

Vaccine

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“…Sinigrin and the derived allyl isothiocyanate are responsible for the pungent taste of black mustard seeds, horseradish and wasabi. Hence, synthetic allyl isothiocyanate is used in agriculture as an insecticide, a bactericide [15] and a nematocide, and also for certain cases of crop protection [16]. Sinalbin and glucotropaeolin and the derived benzyl isothiocyanates are found in high concentration in seeds of white mustard, nasturtium and garden cress.…”

Section: Properties and Biological Activity Of Glucosinolatesmentioning

confidence: 99%

Sulforaphane and related mustard oils in focus of cancer prevention and therapy

Herr¹,

Lozanovski

Houben

et al. 2012

Wien Med Wochenschr

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The plant family Brassicaceae, formerly Cruciferae, contains mustard oil glycosides, from which mustard oils are enzymatically hydrolyzed. Mustard oils offer protection from pests, microorganisms and fungi. More than 120 different mustard oils with various biological functions are known. Since ancient times, these substances are used as natural antibiotics, antiviral drugs and antimycotics. The antioxidative effect of mustard oils contributes to protection from DNA damage. Epidemiological and experimental studies have shown preventive and therapeutic effects of crucifers or isolated substances thereof. Particularly well studied is the mustard oil sulforaphane, which is contained in high concentrations in broccoli and its sprouts. As has been shown in mice recently, sulforaphane also targets the most malignant cancer stem cells, which are not affected by conventional cancer treatments. Based on these promising results, the first prospective clinical studies with cancer patients and sulforaphane-enriched broccoli sprouts have now been initiated in the United States.

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“…One of the primary tenets of “green” chemistry is to develop new atom-economical and energy-efficient industrial processes that contribute to reducing the environmental impact associated with production of commodity and fine chemicals . In this regard, organic isothiocyanates RNCS (ITCs) are a valuable class of synthetic building blocks for the assembly of more complex sulfur- and nitrogen-containing molecular frameworks . Methyl isothiocyanate (MITC), which is the most industrially significant member of this family, is produced on the multikiloton scale through thermal rearrangement of methyl thiocyanate, which is obtained itself through methylation of thiocyanate anion. , Other alkyl and aryl isothiocyanates, however, have often been prepared through the traditional route of reacting an amine with thiophosgene (Cl 2 CS) .…”

Section: Introductionmentioning

confidence: 99%

Catalytic Production of Isothiocyanates via a Mo(II)/Mo(IV) Cycle for the “Soft” Sulfur Oxidation of Isonitriles

2016

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In the presence of excess amounts of elemental sulfur, the dimolybdenum dinitrogen complex {Cp*Mo[N(iPr)C(Ph)N(iPr)]}2(μ-N2) (4; Cp* = η5-C5Me5) serves as a precatalyst for the production of isothiocyanates from isonitriles via highly efficient and atom-economical metal-mediated sulfur atom transfer (SAT) under mild conditions. Mechanistic and structural studies support a catalytic cycle for SAT involving initial formation of a Mo(II) bis(isonitrile) complex that then undergoes sulfination to generate a formal “side-bound” Mo(IV) κ2-(C,S)-isothiocyanate as the key intermediate. This metal-catalyzed SAT process has further been employed for the “on-demand” production of isothiocyanates that are trapped in situ by benzhydrazides to provide thiosemicarbazides, which are useful precursors to biologically active thiadiazoles.

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Thiocyanates and Isothiocyanates, Organic

Abstract: The article contains sections titled: 1. Organic Thiocyanates 1.1. Introduction … Show more

Cited by 9 publications

References 36 publications

A novel retinoic acid, catechin hydrate and mustard oil-based emulsion for enhanced cytokine and antibody responses against multiple strains of HIV-1 following mucosal and systemic vaccinations

A novel retinoic acid, catechin hydrate and mustard oil-based emulsion for enhanced cytokine and antibody responses against multiple strains of HIV-1 following mucosal and systemic vaccinations

Sulforaphane and related mustard oils in focus of cancer prevention and therapy

Catalytic Production of Isothiocyanates via a Mo(II)/Mo(IV) Cycle for the “Soft” Sulfur Oxidation of Isonitriles

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