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Isothiocyanate

 
Isothiocyanate

 
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Isothiocyanate
 
 
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Isothiocyanate is the chemical group -N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
=C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
=S
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
, formed by substituting sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 for oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 in the isocyanate
Isocyanate

Isocyanate is the functional group of atoms ?N=C=O , not to be confused with the cyanate functional group which is arranged as ?O?C=N....
 group. Allyl isothiocyanate
Allyl isothiocyanate

Allyl isothiocyanate is the organosulfur compound with the formula CH2CHCH2NCS. This colourless oil is responsible for the pungent taste of Mustard , horseradish, and wasabi....
 is a chemical compound found in mustard oil
Mustard oil

The term mustard oil is used for three different oils that are made from mustard seeds:* a fatty vegetable oil resulting from pressing the seeds,...
 that is responsible for its pungency. It is used for amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 sequencing in Edman degradation
Edman degradation

Edman degradation, developed by Pehr Edman, is a method of Protein sequencing amino acids in a peptide. In this method, the amino-terminal residue is labeled and cleaved from the peptide without disrupting the peptide bonds between other amino acid residues....
.

hiocyanates generally act as electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
s with the carbon atom as the electrophilic center.


Biological activity
Isothiocyanates, such as phenethyl isothiocyanate (PEITC) and sulforaphane
Sulforaphane

Sulforaphane is an anticancer, antidiabetic, and antimicrobial compound that can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cabbage, cauliflower, bok choy, kale, collards, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, Mustard plant, turnip, radish, Eruca sativa, and watercress....
, have been shown to inhibit carcinogenesis and tumorigenesis and as such are useful chemopreventive agents against the development and proliferation of cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
s.






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Encyclopedia


Isothiocyanate is the chemical group -N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
=C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
=S
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
, formed by substituting sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 for oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 in the isocyanate
Isocyanate

Isocyanate is the functional group of atoms ?N=C=O , not to be confused with the cyanate functional group which is arranged as ?O?C=N....
 group. Allyl isothiocyanate
Allyl isothiocyanate

Allyl isothiocyanate is the organosulfur compound with the formula CH2CHCH2NCS. This colourless oil is responsible for the pungent taste of Mustard , horseradish, and wasabi....
 is a chemical compound found in mustard oil
Mustard oil

The term mustard oil is used for three different oils that are made from mustard seeds:* a fatty vegetable oil resulting from pressing the seeds,...
 that is responsible for its pungency. It is used for amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 sequencing in Edman degradation
Edman degradation

Edman degradation, developed by Pehr Edman, is a method of Protein sequencing amino acids in a peptide. In this method, the amino-terminal residue is labeled and cleaved from the peptide without disrupting the peptide bonds between other amino acid residues....
.

Reactions

Isothiocyanates generally act as electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
s with the carbon atom as the electrophilic center.

Thiazolidinesynthesis

Biological activity


Isothiocyanates, such as phenethyl isothiocyanate (PEITC) and sulforaphane
Sulforaphane

Sulforaphane is an anticancer, antidiabetic, and antimicrobial compound that can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cabbage, cauliflower, bok choy, kale, collards, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, Mustard plant, turnip, radish, Eruca sativa, and watercress....
, have been shown to inhibit carcinogenesis and tumorigenesis and as such are useful chemopreventive agents against the development and proliferation of cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
s. They work on a variety of levels. Most notably, they have been shown to inhibit carcinogenesis through inhibition of cytochrome P450 enzymes, which oxidise compounds such as benzo[a]pyrene and other polycyclic aromatic hydrocarbons (PAHs)into more polar epoxy-diols which can then cause mutation and induce cancer development. Phenethyl isothiocyanate (PEITC) has been shown to induce apoptosis
Apoptosis

Apoptosis is the process of programmed cell death that may occur in multicellular organisms. Programmed Cell death involves a series of biochemical events leading to a characteristic cell Morphology and death, in more specific terms, a series of biochemical events that lead to a variety of morphological changes, including Bleb , changes...
 in certain cancer cell lines, and in some cases, is even able to induce apoptosis in cells that are resistant to some currently used chemotherapeutic drugs. For example, in drug resistant leukemia cells which produce the powerful apoptosis inhibitor protein BCl-2
Bcl-2

Bcl-2 is the prototype for a family of mammalian genes and the proteins they produce. They govern mitochondrial outer membrane permeabilization and can be either pro-apoptosis or anti-apoptotic ....
. Furthermore, isothiocyanates have been the basis of a drug in development which replaces the sulfur bonds with selenium, with far stronger potency against melanoma
Melanoma

Melanoma is a malignant tumor of melanocytes which are found predominantly in skin but also in the bowel and the eye . It is one of the rarer types of skin cancer but causes the majority of skin cancer related deaths....
.

See also

  • methylisothiocyanate
    Methylisothiocyanate

    Methyl isothiocyanate is the organosulfur compound with the chemical formula CH3N=C=S. This low melting colorless solid is a powerful Lachrymatory agent....