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(also mustard oils or isothiocyanate esters), organic compounds having the general formula R—N=C=S, where R is an aliphatic or aromatic radical. Liquids with a pungent odor, they can be distilled without decomposition, are insoluble in water, are lacrimators, and cause burns upon contact with skin. Table 1 gives the properties of some isothiocyanates.

Table 1. Properties of some isothiocyanates
IsothiocyanateBoiling point,
Density, g/cm3
Methyl isothiocyanate  
CH3NCS ......................1191.069 (37°)
Ethyl isothiocyanate  
C2H5NCS ..................1311.003 (18°)
Allyl isothiocyanate  
CH2=CH–CH2NCS ............1501.016 (15°)
Phenyl isothiocyanate  
C6H5NCS .................2221.129 (23°)

Many isothiocyanates are found in plants either in the free state or in the form of glucosides—compounds with sugars or other substances. Allyl isothiocyanate is the pungent and odoriferous component of mustard. Isothiocyanates are quite reactive; they readily add to the N=C bond alcohols, phenols, mercap-tans, and other compounds to give thiocarbamic acid derivatives (R—NH—CX=S, where X = OR, OAr, SH, SR, CN, NH2, and so forth). Addition of carboxylic and thiocarboxylic acids is accompanied by liberation of COS and CS2, respectively, with the formation of acid amides (R—NH—COR’)- Isothiocyanates are hydrolyzed on heating (particularly readily in the presence of acids or alkalies) and are reduced by nascent hydrogen to amines (RNH2); they undergo halogenation with the formation of aminocarbonyl dihalides (R—N=CX2) and react with mercuric oxide, forming isocyanates (R—N=C=O). Isothiocyanates are obtained by thermal isomerization of thiocyanates (R—S—C=N), by decomposition of the derivatives of dithio-carbamic acid or of thiourea, and by other methods.

Many isothiocyanates have bactericidal, fungicidal, and insecticidal properties. Some of them are used, for example, in the production of synthetic fibers.


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Cyclophosphamide-induced urotoxiciy was reduced in Swiss albino mice by the treatment of naturally occurring isothiocyanates such as AITC or PITC (25 [micro]g/dose/animal, i.
2) Cauliflower contains a high concentration of a class of phytochemicals known as glucosinolates, which are metabolized into isothiocyanates.
Dietary organic isothiocyanates are cytotoxic in human breast cancer MCF-7 and mammary epithelial MCF-12A cell lines.
Furthermore, in laboratory models of cellular activity, watercress isothiocyanates restrained certain pro-inflammatory compounds that are associated with chronic inflammation and cancer.
1) hydrolyses glucosinolates to isothiocyanates according to the following mechanism shown in Figure 1.
Exogenously applied isothiocyanates enhance glutathione S-transferase expression in Arabidopsis but act as herbicides at higher concentrations.
Green and yellow vegetables including cabbage, Brussel's sprouts and other cruciferous vegetables contain several organosulfur compounds including isothiocyanates (ITCs) and dithiolethiones.
RESULTS: The isothiocyanates 6-methylsulfinylhexyl isothiocyanate (6-HITC) and sulforaphane (SFN) activated Nrf2 and up-regulated downstream proteins associated with MeHg excretion, such as glutamate-cysteine ligase, glutathione 5-transferase, and multidrug resistance--associated protein, in primary mouse hepatocytes.
Isothiocyanates, for example, are found in cruciferous vegetables, such as broccoli and watercress.
Cruciferous vegetables contain anticarcinogenic isothiocyanates (ITCs), particularly the potent sulforaphane, which may decrease risk of prostate cancer through induction of phase II enzymes, including glutathione S-transferases (GSTs).
Crucifers," including broccoli, cauliflower, brussels sprouts, cabbage, mustard, rutabagas, kohlrabi, kale, and turnips, contain isothiocyanates which also reduce thyroid peroxidase and thyroid hormone formation.
The company has identified isothiocyanates contained in certain cruciferous vegetables such as broccoli, mustard seeds and watercress as having a positive effect on heart health.