Allyl isothiocyanate

Allyl isothiocyanate

Chembox new
Name = Allyl isothiocyanate
ImageFile = Allyl-isothiocyanate-2D-skeletal.png ImageName = Allyl isothiocyanate
ImageFile1 = Allyl-isothiocyanate-3D-vdW.png ImageName1 = Space-filling model of allyl isothiocyanate
IUPACName = 3-isothiocyanato-1-propene
OtherNames = synthetic mustard oil
Section1 = Chembox Identifiers
CASNo = 57-06-7
SMILES = C=CCN=C=S

Section2 = Chembox Properties
Formula = C4H5NS
MolarMass = 99.15 g/mol
Density = 1.013-1.020 g/cm3
MeltingPt = -102 °C
BoilingPt = 148-154 °C

Allyl isothiocyanate is the organosulfur compound with the formula CH2CHCH2NCS. This colourless oil is responsible for the pungent taste of mustard, horseradish, and wasabi. It is slightly soluble in water, but well soluble in most organic solvents.F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.]

Biosynthesis and biological functions

Allyl isothiocyanate comes from the seeds of black mustard ("Brassica nigra") or brown Indian mustard ("Brassica juncea"). When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate.

Allyl isothiocyanate serves the plant as a defense against herbivores; since it is harmful to the plant itself, it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal.

Commericial and other applications

Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate::CH2=CHCH2Cl + KSCN → CH2=CHCH2NCS + KClThe product obtained in this fashion is sometimes known as "synthetic mustard oil." Allyl isothiocyanate can also be liberated by drydistillation of the seeds. The product obtained in this fashion is known as volatile oil of mustard and is usually around 92% pure. It is used principally as a flavoring agent in foods. Synthetic allyl isothiocyanate is used as an insecticide, bacterialcide, and nematocide, and is used in certain cases for crop protection.

Hydrolysis of allyl isothiocyanate gives allyl amine. [OrgSynth | author = M. T. Leffler | title = Allylamine | collvol = 2 | collvolpages = 24 | year = 1943 | prep = CV2P0024]

afety

Allyl isothiocyanate is mildly toxic with ld50 of 151 mg/kg but is a dangerous lachrymator.

References

ee also

* Piperine, the active piquant chemical in black pepper
* Capsaicin, the active piquant chemical in chile peppers
* Allicin, the active piquant flavor chemical in uncooked garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
* List of phytochemicals in food


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  • allyl isothiocyanate — alilizotiocianatas statusas T sritis chemija apibrėžtis Garstyčių sėklų veiklioji medžiaga. formulė CH₂=CHCH₂N=C=S atitikmenys: angl. allyl isothiocyanate rus. аллилизотиоцианат ryšiai: sinonimas – 2 propenilizotiocianatas …   Chemijos terminų aiškinamasis žodynas

  • allyl isothiocyanate — allyl iso·thio·cy·a·nate .ī sō .thī ə sī ə .nāt, nət n a colorless pungent irritating liquid ester C4H5NS that is the chief constituent of mustard oil used in medicine and is used as a flavoring agent and as a medical counterirritant called also… …   Medical dictionary

  • allyl isothiocyanate — noun or allyl mustard oil : a colorless pungent irritating liquid ester CH2=CHCH2NCS that is the chief constituent of mustard oil (sense 1b) and is used as a flavoring agent and as a medical counterirritant …   Useful english dictionary

  • allyl isothiocyanate — noun A pungent compound, CHNCS, obtained from the seeds of black mustard, Brassica negra or prepared synthetically; sometimes known as mustard oil; it is mildly toxic and is used as an animal repellent, etc …   Wiktionary

  • Isothiocyanate d'allyle — Général …   Wikipédia en Français

  • Allyl chloride — Allyl chloride …   Wikipedia

  • Isothiocyanate — General structure of an isothiocyanate Isothiocyanate is the chemical group –N=C=S, formed by substituting sulfur for oxygen in the isocyanate group. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites… …   Wikipedia

  • allyl mustard oil — noun see allyl isothiocyanate …   Useful english dictionary

  • allyl — The monovalent radical, CH2=CHCH2 . a. alcohol a colorless liquid of pungent odor used in making resins and plasticizers; highly irritating to mucous membranes and readily absorbed, causing depression and coma. SYN: vinyl carbinol …   Medical dictionary

  • 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, An essential oil resulting from grinding the seeds, mixing them with water, and extracting the… …   Wikipedia

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