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Allyl isothiocyanate

Aroma
Product Name
Allyl isothiocyanate
CAS No.
57-06-7
Chemical Name
Allyl isothiocyanate
Synonyms
FEMA 2034;1-Propene, 3-isothiocyanato-;allylisothiocyanate,inhibited;AITK;Redskin;senfoel;Senf oel;carbospol;NCI-C50464;femano.2034
CBNumber
CB8853857
Molecular Formula
C4H5NS
Formula Weight
99.15
MOL File
57-06-7.mol
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Allyl isothiocyanate Property

Melting point:
-80 °C
Boiling point:
151 °C
Density 
1.013 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.529(lit.)
FEMA 
2034 | ALLYL ISOTHIOCYANATE
Flash point:
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
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
Stability:
Stable. Combustible. Incompatible with oxidizing agents, acids, water, alcohols, strong bases, amines. Darkens on aging.
LogP
2.15
CAS DataBase Reference
57-06-7(CAS DataBase Reference)
NIST Chemistry Reference
Allyl isothiocyanate(57-06-7)
IARC
3 (Vol. 73, Sup 7) 1999
EPA Substance Registry System
Allyl isothiocyanate (57-06-7)
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Safety

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
8-9-13-19
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29309070
Hazardous Substances Data
57-06-7(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 339 mg/kg (Jenner)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
377430
Product name
Allyl isothiocyanate
Purity
contains BHT as stabilizer, 95%
Packaging
5G
Price
$34.9
Updated
2024/03/01
Sigma-Aldrich
Product number
377430
Product name
Allyl isothiocyanate
Purity
contains BHT as stabilizer, 95%
Packaging
100G
Price
$62
Updated
2024/03/01
Sigma-Aldrich
Product number
377430
Product name
Allyl isothiocyanate
Purity
contains BHT as stabilizer, 95%
Packaging
500G
Price
$109
Updated
2024/03/01
Sigma-Aldrich
Product number
36682
Product name
Allyl isothiocyanate
Purity
PESTANAL?, analytical standard
Packaging
1g
Price
$62.6
Updated
2024/03/01
Alfa Aesar
Product number
L02901
Product name
Allyl isothiocyanate, 94%
Purity
stab.
Packaging
5g
Price
$24.3
Updated
2023/06/20
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Allyl isothiocyanate Chemical Properties,Usage,Production

Aroma

In spite of its apparent power and pungency, allyl isothiocyanate can be tolerated in surprisingly high concentration as a flavor chemical. However, the pungency is perceptible down to a level of 1-3 ppm in aqueous solution.
Used quite extensively in flavor compositions, particularly along with vinegar (pickled products). Also in meat and spice flavors. Concentration in pickled products may be as high as 80 ppm.

Chemical Properties

Allyl Isothiocyanate 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.

Production Methods

Producted from Allyl iodide and Potassium sulfocyanide. Allyl isothiocyanate is the chief component of the volatile oil of black Mustard seed, and can be isolated by enzymatic breakdown of the glycoside in the seed.

Preparation

By distillation of sodium thiocyanate and allyl chloride

Definition

ChEBI: Allyl isothiocyanate 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.

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

Extremely penetrating, pungent and stinging odor. This chemical is a powerful Iachrymator, and inhalation of its vapors may cause serious damage to human lungs. The liquid and its vapors produce blisters on the human skin. A few grams may kill a man, if the oil is taken internally.

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.

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.

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).

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.

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

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