See Also

Isothiocyanate

Isothiocyanate is the chemical Chemical substance

A chemical substance is any material [i] with a definite chemical composition, no matter where it comes ... 

 group -N Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

=C Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ... 

=S Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ... 

, formed by substituting sulfur Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ... 

 for oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8. ... 

 in the isocyanate Isocyanate

Isocyanate is the functional group [i] of atoms –N=C=O , not to be confused with the cyanate [i] f ... 

 group. Allyl isothiocyanate Allyl isothiocyanate

Allyl isothiocyanate is the chemical compound responsible for the pungent taste of mustard [i] ... 

 is also called mustard oil.

Discussions

  Discussion Features

   Ask a question about 'Isothiocyanate'

   Start a new discussion about 'Isothiocyanate'

   Answer questions about 'Isothiocyanate'

   'Isothiocyanate' discussion forum


Encyclopedia

Isothiocyanate is the chemical Chemical substance

A chemical substance is any material [i] with a definite chemical composition, no matter where it comes ... 

 group -N Nitrogen

Nitrogen is a chemical element [i] which has the symbol N and atomic number [i] 7 in the periodic table [i] ... 

=C Carbon

Carbon is a chemical element [i] in the periodic table [i] that has the symbol [i] C' ... 

=S Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ... 

, formed by substituting sulfur Sulfur

Sulfur or sulphur is the chemical element [i] in the periodic table [i] that has the symbol S' ... 

 for oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8.... 

 in the isocyanate Isocyanate

Isocyanate is the functional group [i] of atoms –N=C=O , not to be confused with the cyanate [i] f ... 

 group. Allyl isothiocyanate Allyl isothiocyanate

Allyl isothiocyanate is the chemical compound responsible for the pungent taste of mustard [i] ... 

 is also called mustard oil.

Reactions

Isothiocyanates generally act as an electrophiles with the carbon atom as the electrophilic center.


How they are found in nature


Isothiocyanates are largely found locked in the form of glucosinolates and are found largely in cruciferous vegetables Cruciferous vegetables

Edible plants in the family Brassicaceae [i] are termed Cruciferous vegetables. ... 

 such as brocolli Broccoli

Broccoli is a plant of the Cabbage [i] family, Brassicaceae [i] . ... 

 and Brussels sprouts Brussels sprout

The Brussels sprout is a cultivar group [i] of Wild Cabbage [i] cultivated fo ... 

, as well as in wasabi Wasabi

Wasabi is a member of the cabbage [i] family. ... 

  and watercress Watercress

Watercress are fast-growing, aquatic or semi-aquatic, perennial [i]s native from Europe [i] to central Asia [i] ... 

. Such plants contain an enzyme termed myrosinase which can induce a rearrangement of the glucosinolates leading to the generation of the free isothiocyanate.

Biological Activity


Isothiocyanates, such as phenethyl isothiocyanate and sulforaphane, have been shown to inhibit carcinogenesis and tumorigensis and as such are useful chemopreventive agents against the development and proliferation of cancers. 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 into more polar epoxy-diols which can then cause mutation and induce cancer development. Phenethyl isothiocyanate has been shown to induce apoptosis 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.

See also

  • methylisothiocyanate Methylisothiocyanate

    Methylisothiocyanate, CH3N=C=S, also known by the acronymn MITC, is a low melting colorless solid used i... 

     

References

  1. Improved approaches in the synthesis of new 2-acetophenones M. Carmen Ortega-Alfaro, José G. López-Cortés, Hiram Rangel Sánchez, Rubén A. Toscano, Guillermo Penieres Carrillo, and Cecilio Álvarez-Toledano Arkivoc  pp 356-365 2005





Categories: