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Allyl isothiocyanate

Allyl isothiocyanate Basic information
Product Name:Allyl isothiocyanate
Product Categories:thioester Flavor;VIOFORM
Mol File:57-06-7.mol
Allyl isothiocyanate Structure
Allyl isothiocyanate Chemical Properties
Melting point -80 °C
Boiling point 151 °C
density 1.013 g/mL at 25 °C(lit.)
refractive index n20/D 1.529(lit.)
Fp 115 °F
storage temp. 2-8°C
form Fine Crystalline Powder
color White
Water Solubility 2 g/L (20 ºC)
Sensitive Moisture Sensitive
Merck 14,295
JECFA Number1560
BRN 773748
Stability:Stable. Combustible. Incompatible with oxidizing agents, acids, water, alcohols, strong bases, amines. Darkens on aging.
CAS DataBase Reference57-06-7(CAS DataBase Reference)
IARC3 (Vol. 73, Sup 7) 1999
NIST Chemistry ReferenceAllyl isothiocyanate(57-06-7)
EPA Substance Registry SystemAllyl isothiocyanate (57-06-7)
Safety Information
Hazard Codes T,N
Risk Statements 10-24/25-36/37/38-42/43-50/53-43-23/24/25-34-25
Safety Statements 26-36/37-45-60-61-36/37/39-28B-24-16-23-7/8
RIDADR UN 1545 6.1/PG 2
WGK Germany 3
RTECS NX8225000
HazardClass 6.1
PackingGroup II
HS Code 29309070
Hazardous Substances Data57-06-7(Hazardous Substances Data)
ToxicityLD50 orally in rats: 339 mg/kg (Jenner)
MSDS Information
Allyl isothiocyanate English
SigmaAldrich English
ALFA English
Allyl isothiocyanate Usage And Synthesis
Chemical PropertiesA colorless liquid with very pungent, irritating odor and acrid taste; lacrimatory
Chemical Propertiescolourless or light amber oily liquid
Chemical PropertiesAllyl Isothiocyanate is the main component of mustard oil (>95%). It is a colorless oil with a typical mustard odor and can be prepared by reacting allyl chloride with alkaline-earth or alkali rhodanides.
Chemical PropertiesAllyl isothiocyanate is a highly flammable, colorless to pale yellow, oily liquid. Air contact may cause darkening. Pungent, irritating odor and acrid taste
OccurrenceIn the essential oil from seeds of Brassica nigra Koch, Brassica juncea Hook. and Thoms., and Thlaspi arvense; in the essential oil from roots of Cochlearia armoracia; in the seeds and roots of Alliaria officinalis; in onion juice; and in the seeds of various Cruciferae. Reported found in pineapple (Anans comoscus), raw cabbage, cooked cabbage, sauerkraut, milk, heated beans, horseradish (Armoracia lapathifolia), raw cauliflower, Brussels sprouts, turnip, Chinese cabbage, wasabi (Japanese horseradish) (Wasabi japonica).
Usesantiseptic, antiamebic
UsesAllyl Isothiocyanate is a synthetic flavoring agent that is a moder- ately stable, colorless to pale yellow liquid of pungent and irritating odor. it should be stored in glass containers. it is used as an artificial oil of mustard and as an imitation horseradish flavor with applica- tion in condiments, meats, and pickles at 87 ppm. it is also termed mustard oil.
Usesmanufacture of flavors; war gas.
PreparationBy distillation of sodium thiocyanate and allyl chloride
Synthesis Reference(s)Tetrahedron Letters, 32, p. 3503, 1991 DOI: 10.1016/0040-4039(91)80817-P
General DescriptionA colorless to pale-yellow oily liquid with an irritating odor. Flash point 135°F. Boiling point 300°F. Poisonous by ingestion and skin absorption. Emits toxic fumes when heated to high temperature. Insoluble in water and slightly denser than water. Hence sinks in water. Used to make other chemicals and as a fumigant.
Air & Water ReactionsFlammable. Insoluble in water.
Reactivity ProfileA routine preparation by interaction of allyl chloride and sodium thiocyanate in an autoclave at 5.5 bar exploded violently at the end of the reaction. Peroxides were not present or involved and no other cause could be found, but extensive decomposition occurred when allyl isothiocyanate was heated to 250°C. in glass ampoules [Ind. Eng. Chem. 1941:19 1408].
HazardToxic via ingestion, inhalation, skin con- tact; fire risk. Questionable carcinogen.
Health HazardTOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Contact allergensAllyl isothiocyanate is generated by enzymatic hydrolysis of the glucoside sinigrin, present in Cruciferae- Brassicaceae, mainly the oil from black mustard seed (Brassica nigra Koch). It may induce irritant and sometimes allergic contact dermatitis, mimicking the “tulip finger” dermatitis.
Anticancer ResearchThis compound was tested on Ehrlich ascites tumor cells transplanted in Swissalbino mice using HEK293 cells as control. There was a significantly reduced ascitessecretion and tumor cell proliferation. Also the vascular endothelial growth factorexpression was inhibited. The apoptosis was induced in tumor cells, and cellcycle was arrested at G1 phase (Ichwan et al. 2014).
Safety ProfileSuspected carcinogen with experimental neoplastigenic and tumorigenic data. Poison by ingestion, skin contact, intravenous, subcutaneous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. An eye irritant. An allergen. May cause contact dermatitis. Mutation data reported. A flammable liquid. Highly reactive. When heated to decomposition (above 250') or on contact with acid or acid fumes it emits highly toxic fumes of CN-, SO,, and NOx. To fight fire, use foam, CO2, dry chemical. See also ALLYL COMPOUNDS and ESTERS.
Potential ExposureUsed in fumigants, veterinary drugs, ointments and counter irritants, mustard plasters, and as a flavoring agent.
ShippingUN1545 Allyl isothiocyanate, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3 flammable liquids.
Purification MethodsFractionate the isothiocyanate using an efficient column, preferably in a vacuum. It is a yellow pungent, irritating and TOXIC (suspected CARCINOGEN) liquid. Store it in a sealed tube under N2. The N'-benzylthiourea derivative has m 94.5o (from aqueous EtOH) [Weller et al. J Am Chem Soc 74 1104 1952]. [Beilstein 4 IV 1081.]
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alcohols, amines
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