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Topic: Allyl isothiocyanate

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	Mustard oil - Wikipedia, the free encyclopedia
		Allyl isothiocyanate can also be produced synthetically, and is sometimes known as synthetic mustard oil.
		Because of the contained allyl isothiocyanate, this type of mustard oil is toxic and irritates the skin and mucous membranes.
		The CAS number of this type of mustard oil is 8007-40-7, and the CAS number of pure allyl isothiocyanate is 57-06-7.
	en.wikipedia.org /wiki/Mustard_oil (585 words)

	Isothiocyanate - Wikipedia, the free encyclopedia
		Isothiocyanates act as electrophiles with the carbon atom as the electrophilic center.
		This is demonstrated by the reaction of the acetophenone enolate with phenyl isothiocyanate.
		This reaction is stereoselective with the formation of the Z-isomer only as evidenced by the Nuclear Overhauser effect in the proton NMR spectrum.
	en.wikipedia.org /wiki/Isothiocyanate (129 words)

	BoDD (Botanical Dermatology Database) - CRUCIFERAE
		Cole (1976) observed that allyl isothiocyanate together with a small quantity of 2-phenylethyl isothiocyanate was released from the glucosinolates of this plant on autolysis.
		Allyl isothiocyanate is released from the plant material on autolysis of its glucosinolates (Cole 1976).
		Allyl isothiocyanate is released from the plant material on autolysis of its glucosinolates.
	bodd.cf.ac.uk /BotDermFolder/BotDermC/CRUC.html (5558 words)

	Previous eval.: Allyl Isothiocyanate (IARC Summary & Evaluation, Volume 36, 1985) (Site not responding. Last check: 2007-10-15)
		Allyl isothiocyanate is also prepared from the seeds of mustard plants, Brassica nigra and B.
		Allyl isothiocyanate was tested for carcinogenicity by gastric intubation in mice of one strain and in rats of one strain.
		Allyl isothiocyanate was not teratogenic to mice, rats, hamsters or rabbits, but resorptions were seen in mice and rats.
	www.inchem.org /documents/iarc/vol36/allylisothiocyanate.html (258 words)

	Isothiocyanate - Encyclopedia.WorldSearch (Site not responding. Last check: 2007-10-15)
		Isothiocyanate is the chemical group -N=C=S, formed by substituting sulfur for oxygen in the isocyanate group.
		Inhibition of ethylene evolution in papaya pulp tissue by benzyl isothiocyanate (Hawaii Agricultural Experiment Station.
		Benzyl isothiocyanate in the Caricaceae (Hawaii Agricultural Experiment Station.
	encyclopedia.worldsearch.com /isothiocyanate.htm (146 words)

	Thornalley Lab - Chemoprevention of Cancer by Dietary Isothiocyanates (Site not responding. Last check: 2007-10-15)
		Isothiocyanates and cysteine conjugates had increased potency against HL60 cells in serum-free medium - the GC values were 0.8-0.9 µM; the potency of the compounds decreased with increased serum content of the medium but that of the cysteine conjugates decreased more markedly.
		Growth inhibition and toxicity was characterized by a rapid interaction of the isothiocyanate with the cells in the first hour of culture – or exposure to isothiocyanate liberated from the cysteine conjugate in the initial 3 h of culture, inhibition of macromolecule synthesis and commitment to apoptosis which developed in the initial 24 h.
		S-(N-phenethylthiocarbamoyl)glutathione spontaneously fragmented to GSH and phenethyl isothiocyanate: GSH oxidized to GSSG and glutathionyl-protein disulphides, and phenethyl isothiocyanate hydrolyzed to phenylethylamine.
	www.essex.ac.uk /bs/staff/thornalley/homepage/research_interests/isothiocyanates (1827 words)

	Last eval.: Allyl Isothiocyanate (Vol73) (Site not responding. Last check: 2007-10-15)
		Exposure to allyl isothiocyanate occurs as a result of its presence in foods as the chief constituent of mustard oil and as a flavouring agent.
		Allyl isothiocyanate was tested for carcinogenicity in one experiment in mice and one experiment in rats by oral administration.
		Major sex- and species-related differences in the tissue distribution of allyl isothiocyanate were restricted to the urinary bladder, where higher concentrations of allyl isothiocyanate-derived radiolabel were found in the bladders of male rats than in mice or female rats.
	monographs.iarc.fr /htdocs/monographs/vol73/73-01.html (268 words)

	University of Manitoba: Agricultural & Food Sciences - Farmers Independent Weekly October 16, 2003
		Allyl isothiocyanate is formed from a conversion of glucosinolate compounds at approximately 0.5 to 1% of the mustard seed by weight - at least in the fl mustard species which is grown extensively in Canada.
		It was also postulated that other components in the mustard flour may have synergistic roles with allyl isothiocyanate in causing destruction of the E.coli O157:H7.
		Our research also concluded that addition of allyl isothiocyanate extract in a concentrated form to packaged hamburger meat was not as effective as mixing in the "hot mustard" powder in the destruction of E.coli O157:H7.
	www.umanitoba.ca /afs/fiw/031016.html (487 words)

	Spice Pages: Black Mustard Seeds (Brassica nigra/juncea)
		By action of the enzyme myrosinase, allyl isothiocyanate, a pungent, lachrymatory and volatile compound, is liberated (0.7% of the dried seed).
		Isothiocyanates are also the main ingredients of white mustard, horseradish, wasabi, rocket and cress, all of which belong to the same plant family.
		However, because of the erucic acid and maybe also the isothiocyanates, mustard oil is not a legal foodstuff in most western countries, including the EU and the USA, and it must not be sold as cooking oil.
	www-ang.kfunigraz.ac.at /~katzer/engl/Bras_nig.html (1302 words)

	RedNova News - Science - Dietary Isothiocyanates Inhibit Caco-2 Cell Proliferation and Induce G^Sub 2^/M Phase Cell ... (Site not responding. Last check: 2007-10-15)
		Benzyl isothiocyanate and phenethyl isothiocyanate, two aromatic phytochemicals present in substantial concentrations in edible vegetables of the genus Brassica, were investigated for their effects on Caco-2 cell proliferation.
		These results suggest that the antiproliferative effects of benzyl and phenethyl isothiocyanates toward Caco-2 cells are due at least in part to the activation of the G^sub 2^/M DNA damage checkpoint, and that sustained G^sub 2^/M phase cell cycle arrest in response to benzyl and phenethyl isothiocyanates may be maintained through upregulation of p21.
		Allyl ITC was also shown to inhibit cell proliferation through the induction of G^sub 2^/M phase cell cycle arrest, although not all cell lines were equally susceptible to allyl ITC (16).
	www.rednova.com /news/display/?id=106448 (4251 words)

	180.1167 Allyl isothiocyanate as a component of food grade oil of mustard; exemption from the requirement of a ... (Site not responding. Last check: 2007-10-15)
		180.1167 Allyl isothiocyanate as a component of food grade oil of mustard; exemption from the requirement of a tolerance.
		§ 180.1167 Allyl isothiocyanate as a component of food grade oil of mustard; exemption from the requirement of a tolerance.
		The insecticide and repellent Allyl isothiocyanate is exempt from the requirement of a tolerance for residues when used as a component of food grade oil of mustard, in or on all raw agricultural commodities, when applied according to approved labeling.
	www.setonresourcecenter.com /40CFR/Docs/wcd0004c/wcd04c66.asp (79 words)

	BioMed Central \| Full text \| Glucosinolate breakdown products as insect fumigants and their effect on carbon dioxide ...
		Significantly increased CO expiration was found in insects exposed to the vapor of allyl isothiocyanate, allyl thiocyanate and allyl isocyanate.
		Allyl glucosinolate (sinigrin) breaks down in soils to allyl isothiocyanate and allyl cyanide, and these breakdown products and glucosinolate-containing plant tissue have been suggested for use in controlling soil-borne plant pests [9,15-19].
		Allyl thiocyanate was synthesized in this laboratory by reacting allyl chloride with potassium thiocyanate (KSCN) in dimethyl sulfoxide (DMSO).
	www.biomedcentral.com /1472-6785/2/5 (3912 words)

	Resins and Versatics - Allyl chloride
		Allyl chloride (3-chloropropene) is a colorless, mobile liquid with a characteristic pungent odor.
		Important intermediates derived from allyl chloride are glycerol chlorohydrins, epichlorohydrin, glycerol and glycidyl ethers, allylamines, and allyl ethers of trimethylolpropane.
		Allyl chloride has been used to prepare allyl ethers of starch which are of some interest in surface coatings.
	www.resins.com /resins/am/products/AC.html (212 words)

	NTP: Abstract for TR-234 - Allyl Isothiocyanate
		The increased incidence of cytoplasmic vacuolization in the liver of dosed male mice was related to administration of allyl isothiocyanate (controls, 2/49, 4%; low-dose, 8/49, 16%; high-dose, 13/50, 26%).
		Under the conditions of this bioassay, allyl isothiocyanate was carcinogenic for male F344/N rats, causing transitional-cell papillomas in the urinary bladder.
		Evidence for associating allyl isothiocyanate with subcutaneous fibrosarcomas in female F344/N rats was equivocal.
	ntp-server.niehs.nih.gov /index.cfm?objectid=070654C2-FBED-FAFA-564F802B36ACA523 (545 words)

	allyl isothiocyanate Exemption From the Requirement of a Tolerance 5/96
		to establish an exemption from the requirement of a tolerance for allyl isothiocyanate (a component of oil of mustard) in or on all fruits and vegetables, nuts, berries, and grains." There were no public comments received as a result of the publication of the notice of filing.
		Allyl isothiocyanate, the subject of this exemption request, is a component of Oil of Mustard.
		Allyl isothiocyanate, as a component of oil of mustard, is on the Food and Drug Administration (FDA) Generally Recognized as Safe (GRAS) list (21 CFR 182.10, 182.20, 582.10 and 582.20).
	pmep.cce.cornell.edu /profiles/rodent/allyl-isothio/tol-ex-allyl-isothio.html (1331 words)

	MUSTARD
		The enzymatic action of myrosin on the glucoside sinigrin in fl and brown mustard or on sinalbin in white mustard releases the mustard oil, which consists principally of allyl isothiocyanate in fl and brown mustards and of p-hydroxybenzyl isothiocyanate in white mustard, the compounds responsible for the pungency (1.5-151, 1.6-41).
		The steam-extracted volatile oil of fl and brown mustard is about 94% allyl isothiocyanate, and it also contains some allyl cyanide and carbon disulfide (14.1-11).
		Isothiocyanate in mustard oil considered poisonous and mutagenic, has induced goiter in laboratory animals (7.6-5).
	www.hort.purdue.edu /newcrop/med-aro/factsheets/MUSTARD.html (741 words)

	Horseradish
		The pungent principle of horseradish is allyl isothiocyanate, which is enzymatically produced from sinigrin (see fl mustard seeds).
		The pungent allyl isothiocyanate is not heat resistant; therefore, horseradish is only seldom used for warm dishes and then added immediately before serving.
		Even in cold water, allyl isothiocyanate is not stable for longer than a few minutes.
	www.linebylineproductions.com /My%20Spices/horseradish.htm (497 words)

	US Dispensatory, 1918: Oleum Sinapis Volatile. Volatile Oil of Mustard, Mustard Oil. (Site not responding. Last check: 2007-10-15)
		(allyl isothiocyanate), it being related to oil of garlic, which is sulphide of allyl.
		What first forms is allyl sulphocyanate, which is not identical with, but only an isomer of, mustard oil (allyl isosulphocyanate).
		Allyl iodide is procured by treating glycerin with phosphorus iodide.
	www.ibiblio.org /herbmed/eclectic/usdisp/sinapis_oleu.html (713 words)

	Mustard oil (Brassica nigra).
		The powder or seed does not contain allyl isothiocyanate and is only formed during the production of the essential oil.
		As an essential oil, mustard oil is toxic because of its high content of allyl isothiocyanate and also is a skin and mucus membrane irritant.
		Although mustard seeds and powder do not contain allyl isothiocyanate, it is formed when the seeds came in contact with water and the essential oil is formed when a glycoside decomposes due to enzymatic action.
	www.essentialoils.co.za /essential-oils/mustard.htm (372 words)

	James MacDonald Final Report (Site not responding. Last check: 2007-10-15)
		This is because production of these specialty crops tends to be dispersed on many small parcels of land near homes and business, and cannot easily accommodate the ever-increasing buffer zone requirements.
		The goal of this project was to research the efficacy of biofumigation, an effect created by the decomposition of Brassicaceae (e.g., broccoli, cauliflower, mustards) in soil to release isothiocyanates (ITCs).
		Isothiocyanates are formed naturally by the breakdown of glucosinolates-complex compounds that are formed within plant tissues of species of Brassicaceae.
	www.sarep.ucdavis.edu /grants/Reports/MeBr/MacDonald/macdonaldfinal.html (4243 words)

	Broccoli sprouts: An exceptionally rich source of inducers of enzymes that protect against chemical carcinogens -- ...
		Extraction and Quantitation of Glucosinolates and Isothiocyanates from Crucifers.
		The isothiocyanate sulforaphane was isolated from acetonitrile extracts of lyophilized aqueous homogenates of broccoli and
		QR, quinone reductase [NAD(P)H:(quinone-acceptor) oxidoreductase, EC 1.6.99.2]; DMBA, 7,12-dimethylbenz(a)anthracene; glucoraphanin, the glucosinolate of sulforaphane or 4-methylsulfinylbutyl isothiocyanate [CH glucoerucin, the glucosinolate of erucin or 4-methylthiobutyl isothiocyanate [CH glucobrassicin, indol-3-ylmethyl glucosinolate; neoglucobrassicin, 1-methoxyindol-3-ylmethyl glucosinolate; 4-hydroxyglucobrassicin, 4-hydroxyindol-3-ylmethyl glucosinolate; fr.
	www.pnas.org /cgi/content/full/94/19/10367 (5296 words)

	Solvay Chemicals - Products: Allyl Chloride (Site not responding. Last check: 2007-10-15)
		Allyl chloride is a chemical intermediate used in many applications.
		The largest allyl chloride market is the manufacture of quaternary ammonium flocculants for raw and potable water clarification.
		Other key chemicals made from allyl chloride include a variety of allylamines which are used for the production of ion exchange resins, polymers, and specialty products.
	www.solvaychemicals.us /AllylChloride.htm (215 words)

	Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers -- ...
		The inclusion of the watercress autolysate was to quantify postabsorptive
		output as a proportion of allyl isothiocyanate ingested was
		-cysteine, a principal metabolite of alkyl isothiocyanates in rat urine.
	cebp.aacrjournals.org /cgi/content/full/13/1/125 (4305 words)

	Re: Why does fresh hot mustard burn the back of your nose when you chew ?
		Like the "hot oils" found in peppers, which are generally capsaicins and related compounds, allyl isothiocyanate is very irritating to mucous membranes, and for some reason many of us like it.
		Allyl isothiocyanate evaporates more readily on your tongue and floats its way up into your sinuses (yes, as a gas), which is why both your mouth and nose burn when you eat something with horseradish or mustard in it.
		It is also why the burn from these foods tends to fade after a few seconds, while the burn from Mexican food can stay with you for a good long time.
	www.madsci.org /posts/archives/2004-06/1087579957.Bc.r.html (254 words)

	References (Site not responding. Last check: 2007-10-15)
		Borek, V., Morra, M.J., Brown, P.D., and McCaffrey, J.P. Transformation of the Glucosinolate-derived Allelochemicals Allyl Isothiocyanate and Allyl Nitrile in Soil.
		Gaind, K.N., Gandhi, K.S., Juneja, T.R., Kjaer, A., and Nielsen B.J. 4,5,6,7-Tetrahydroxydecyl Isothiocyanate derived from a Glucosinolate in Capparis grandis.
		Lam, W.W., Kim, J.H., Sparks, S.E., Quistad, G.B., and Casida, J.E. Metabolism in Rats and Mice of the Soil Fumigants Metham, Methyl Isothiocyanate, and Dazomet.
	soils.ag.uidaho.edu /mmorra/gluc/references.htm (7840 words)

	Allelopathy: The Effects of Chemicals Produced by Plants (Site not responding. Last check: 2007-10-15)
		Isothiocyanate concentrations in the soil were measured using infrared analysis of CCl4 extracts, and ionic thiocyanate (SCN-) using ion chromatography on aqueous extracts.
		Isothiocyanate production reached a maximum of 301 nmol/g soil at 2 hr, but decreased by 90% within 24 hr.
		Language: English Descriptors: Brassica napus; Allyl isothiocyanate; Biosynthesis; Allelopathins; Plant interaction; Growth inhibitors; Plant density; Mutants; Genotypes; Genetic variation Abstract: The allelopathic potential of Brassica species has been attributed to release of the mustard oil glycosides which they produce in large quantities.
	www.nal.usda.gov /afsic/AFSIC_pubs/qb94-56.htm (14624 words)

	Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers -- ...
		Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers -- Rouzaud et al.
		Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers
		raw cabbage consumption, allyl isothiocyanate was again rapidly
	cebp.aacrjournals.org /cgi/content/abstract/13/1/125 (258 words)

	AllAllergy.Net - Allergy Advisor Digest (Site not responding. Last check: 2007-10-15)
		Allergic contact dermatitis from allyl isothiocyanate is well known but infrequently reported.
		The aim of this study was to investigate the prevalence of contact allergy to allyl isothiocyanate in patients with suspected contact dermatitis from vegetables and food.
		These were analysed with high-performance liquid chromatography, and a moderate concentration of allyl isothiocyanate (2.5 ppm) was detected in the sample of margarine.
	www.allallergy.net /abstracts/index.cfm?ShowMonth=December2004 (3928 words)

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