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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
Molecular Weight:
99.15
MDL Number:
MFCD00004822
MOL File:
57-06-7.mol
Last updated:2023-11-28 16:31:44

Allyl isothiocyanate 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.)
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
Merck 14,295
JECFA Number 1560
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
Substances Added to Food (formerly EAFUS) ALLYL ISOTHIOCYANATE
SCOGS (Select Committee on GRAS Substances) Allyl isothiocyanate
Mustard and Oil of Mustard (Brown and Yellow)
FDA 21 CFR 310.545
CAS DataBase Reference 57-06-7(CAS DataBase Reference)
FDA UNII BN34FX42G3
IARC 3 (Vol. 73, Sup 7) 1999
NIST Chemistry Reference Allyl isothiocyanate(57-06-7)
EPA Substance Registry System Allyl isothiocyanate (57-06-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS05,GHS06,GHS09
Signal word  Danger
Hazard statements  H226-H302-H310+H330-H314-H317-H410
Precautionary statements  P210-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
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
Toxicity LD50 orally in rats: 339 mg/kg (Jenner)
NFPA 704
2
3 1

Allyl isothiocyanate price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 377430 Allyl isothiocyanate contains BHT as stabilizer, 95% 57-06-7 5G $34.9 2024-03-01 Buy
Sigma-Aldrich 377430 Allyl isothiocyanate contains BHT as stabilizer, 95% 57-06-7 100G $62 2024-03-01 Buy
Sigma-Aldrich 377430 Allyl isothiocyanate contains BHT as stabilizer, 95% 57-06-7 500G $109 2024-03-01 Buy
Sigma-Aldrich 36682 Allyl isothiocyanate PESTANAL?, analytical standard 57-06-7 1g $62.6 2024-03-01 Buy
Alfa Aesar L02901 Allyl isothiocyanate, 94% stab. 57-06-7 5g $24.3 2023-06-20 Buy
Product number Packaging Price Buy
377430 5G $34.9 Buy
377430 100G $62 Buy
377430 500G $109 Buy
36682 1g $62.6 Buy
L02901 5g $24.3 Buy

Allyl isothiocyanate Chemical Properties,Uses,Production

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.

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

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.

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

540-72-7
107-05-1
57-06-7
Synthesis of Allyl isothiocyanate from Sodium thiocyanate and Allyl chloride
allylisorhodanide allylisosulfocyanate Allyliso-sulfocyanate allylisosulphocyanate allylisothiokyanat Allylsenevol Allylsenfoel Allylsevenolum allylthiocarbonimide artificialmustardoil artificialoilofmustard carbospol femano.2034 femanumber2034 Isothiocyanate d'allyle isothiocyanated’allyle isothiocyanated’allyle(french) NCI-C50464 Oil of mustard Oil of mustard, artificial oilofmustard oilofmustard,artificial oilofmustardbpc1949 Oleum sinapis Oleum sinapis volatile oleumsinapis oleumsinapisvolatile Propene, 3-isothiocyanato- Redskin Senf oel 3-ISOTHIOCYANATO-1-PROPENE ALLYL ISOTHIOCYANATE ALLYL MUSTARD OIL 2-PROPENYL ISOTHIOCYANATE AITK Isothiocyanato-1-propene Propenyl isothiocyanate ally isothiocyanate allyl isorhodanate ALLYL ISOTHIOCYANATE 93+% FCC Allyl #niso-thiocyanate ALLYL ISO-THIOCYANATE STABILIZED, PESTAN AL Allylisothiocyanat Allylisothiocyanate,94% Propylene 3-isothiocyanate Allyl isothiocyanate, stabilized, 94% allylisothiocyanate,allyspol,3-isothiocyanato-1-propene Allyl Isothiocyanate (Mustard Oil) , Synthetic allyl isosulfocyanide ALLYL ISOTHIOCYANATE 10% IN POLYSORBATE 80 ALLYL ISOTHIOCYANATE 10% IN SOYBEAN OIL ALLYL ISOTHIOCYANATE, NATURAL ISOTHIOCYANIC ACID ALLYL ESTER AITC, Oil of mustard Isothiocyanic acid allyl Allyl isothiocyanate, 94%, stab. Allyl isothiocyanate,94%,stabilized with 0.01% alpha-tocopherol ALLYL ISOTHIOCYANATE(SG)