| Identification | More | [Name]
Allyl isothiocyanate | [CAS]
57-06-7 | [Synonyms]
2-PROPENYL ISOTHIOCYANATE
3-ISOTHIOCYANATO-1-PROPENE
ALLYL ISOTHIOCYANATE
ALLYL MUSTARD OIL
FEMA 2034
ISOTHIOCYANIC ACID ALLYL ESTER
MUSTARD OIL
MUSTARD OIL (SYNTHETIC)
VOLATILE OIL OF MUSTARD
1-Propene, 3-isothiocyanato-
1-Propene,3-isothiocyanato-
3-isothiocyanato-1-propen
3-iso-Thiocyanatoprop-1-ene
3-isothiocyanato-prop-1-ene
3-isothiocyanato-propen
3-isothiocyanato-propene
Allyl isosulfocyanate
Allylisocyanat
allylisorhodanide
allylisosulfocyanate | [EINECS(EC#)]
200-309-2 | [Molecular Formula]
C4H5NS | [MDL Number]
MFCD00004822 | [Molecular Weight]
99.15 | [MOL File]
57-06-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Allyl isothiocyanate is a highly flammable, colorless to pale yellow, oily liquid. Air contact may cause darkening. Pungent, irritating odor and acrid taste | [Melting point ]
-80 °C | [Boiling point ]
151 °C | [density ]
1.013 g/mL at 25 °C(lit.) | [FEMA ]
2034 | [refractive index ]
n20/D 1.529(lit.)
| [Fp ]
115 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Fine Crystalline Powder | [color ]
White | [Odor]
at 0.01 % in propylene glycol. strong pungent mustard | [Stability:]
Stable. Combustible. Incompatible with oxidizing agents, acids, water, alcohols, strong bases, amines. Darkens on aging. | [Odor Type]
sulfurous | [Water Solubility ]
2 g/L (20 ºC) | [Sensitive ]
Moisture Sensitive | [JECFA Number]
1560 | [Merck ]
14,295 | [BRN ]
773748 | [Dielectric constant]
17.199999999999999 | [Contact allergens]
Allyl 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. | [LogP]
2.15 | [CAS DataBase Reference]
57-06-7(CAS DataBase Reference) | [IARC]
3 (Vol. 73, Sup 7) 1999 | [NIST Chemistry Reference]
Allyl isothiocyanate(57-06-7) | [EPA Substance Registry System]
57-06-7(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Allyl Isothiocyanate[57-06-7] is the main component of mustard oil (>95%). It is a highly flammable, colorless to pale yellow, oily liquid with a typical mustard odor. Exposure to air might cause it to darken. It has a pungent, irritating smell and a bitter taste that can cause lacrimatory. It can be synthesized by reacting allyl chloride with alkaline-earth or alkali rhodanides. | [Occurrence]
In 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). | [Uses]
Allyl isothiocyanate, also known as mustard oil, is a synthetic flavoring agent that is used as an artificial oil of mustard and as an imitation horseradish flavor with application in condiments, meats, and pickles at 87 ppm. It has additional applications as an antiseptic, antiamebic, manufacture of flavors and war gas. | [Definition]
ChEBI: Allyl isothiocyanate(CAS: 57-06-7) is an isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152℃, it is responsible for the pungent taste of mustard, horseradish, and wasabi. It has a role as a lachrymator, a metabolite, an antimicrobial agent, an apoptosis inducer and an antineoplastic agent. It is an isothiocyanate and an alkenyl isothiocyanate.
| [Preparation]
By 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 Description]
A 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. It should be stored in glass containers. | [Air & Water Reactions]
Flammable. Insoluble in water. | [Reactivity Profile]
A 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]. | [Hazard]
Toxic via ingestion, inhalation, skin con-
tact; fire risk. Questionable carcinogen.
| [Health Hazard]
TOXIC; 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 Hazard]
HIGHLY 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. | [Anticancer Research]
This 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). | [Potential Exposure]
Used in fumigants, veterinary drugs, ointments and counter irritants, mustard plasters, and as a flavoring agent. | [Shipping]
UN1545 Allyl isothiocyanate, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3 flammable liquids. | [Purification Methods]
Fractionate 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.] | [Incompatibilities]
Incompatible 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 |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R10:Flammable.
R24/25:Toxic in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R43:May cause sensitization by skin contact.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S24:Avoid contact with skin .
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 1545 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
NX8225000
| [F ]
8-9-13-19 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29309070 | [Safety Profile]
Suspected 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. | [Hazardous Substances Data]
57-06-7(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 339 mg/kg (Jenner) |
|