57-06-7 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 57-06-7 differently. You can refer to the following data:
1. colourless or light amber oily liquid
2. Allyl isothiocyanate is a highly flammable, colorless to pale yellow, oily liquid. Air contact may cause darkening. Pungent, irritating odor and acrid taste
3. Allyl 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.
4. A colorless liquid with very pungent, irritating odor and acrid taste; lacrimatory
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
Different sources of media describe the Uses of 57-06-7 differently. You can refer to the following data:
1. Allyl 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.
2. antiseptic, antiamebic
3. manufacture of flavors; war gas.
Preparation
By distillation of sodium thiocyanate and allyl chloride
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 57-06-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 57-06:
(4*5)+(3*7)+(2*0)+(1*6)=47
47 % 10 = 7
So 57-06-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
57-06-7Relevant articles and documents
Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis cv. Woll)
Buskov,Serra,Rosa,Sorensen,Sorensen
, p. 690 - 695 (2002)
The potato cyst nematode (Globodera rostochiensis cv. Woll) is responsible for large yield losses in the potato crop, and opportunities for reducing the attack of these plant nematode species are, therefore, important. This study has been devoted to the testing of the in vitro effects on the potato cyst nematode of eight glucosinolates [prop-2-enyl-, but-3-enyl-, (R)-4-methylsulfinylbut-3-enyl-, benzyl-, phenethyl-, 4-hydroxybenzyl-, (2S)-2-hydroxybut-3-enyl-, and (2R)-2-hydroxy-2-phenylethylglucosinolate] as well as the effects of the products of this myrosinase-catalyzed hydrolysis. The glucosinolates were used at three concentrations, 0.05, 0.3, and 1.0 mg/mL, in the presence or absence of the enzyme myrosinase. The effects of the compounds on the mortality were monitored every 8 h for a 72 h period. No effects were found for any of the intact glucosinolates. However, when active myrosinase was included with 1 mg/mL phenethylglucosinolate at pH 6.5, 100% mortality was observed within just 16 h. A similar effect was achieved at the same concentration of benzyl-and prop-2-enylglucosinolates in the myrosinase-containing solutions, although longer exposures were required (24 and 40 h, respectively). The main aglucone products released from the glucosinolates with pronounced effects on the nematodes were shown to be the corresponding isothiocyanates. The results suggest that mixtures of these specific glucosinolates and active myrosinase or autolysis of plant materials containing these enzymes and glucosinolates might be used to control the potato cyst nematode in the soil.
4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
Gavara, Laurent,Legru, Alice,Verdirosa, Federica,Sevaille, Laurent,Nauton, Lionel,Corsica, Giuseppina,Mercuri, Paola Sandra,Sannio, Filomena,Feller, Georges,Coulon, Rémi,De Luca, Filomena,Cerboni, Giulia,Tanfoni, Silvia,Chelini, Giulia,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
, (2021/06/15)
In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.
Preparation method of allyl isothiocyanate
-
Paragraph 0038-0129, (2020/08/25)
The invention discloses a method for preparing allyl isothiocyanate. The preparation method of allyl isothiocyanate is divided into two steps of allyl isothiocyanate synthesis and allyl isothiocyanaterectification. According to the present invention, the allyl isothiocyanate is synthesized under the solvent condition, the allyl isothiocyanate synthesis process has advantages of mild reaction, lowtemperature, simple operation, no wastewater and the like, the organic solvent is firstly removed during the rectification process, and then rectification is performed to obtain the qualified allyl isothiocyanate standard product.
Preparation method of isothiocyano compound
-
Paragraph 0012, (2019/10/29)
The invention discloses a preparation method of an isothiocyano compound. An ammonium thiocyanate, sodium thiocyanate or potassium thiocyanate water solution and a halide are used as raw materials, and an isothiocyano compound is synthesized under the action of a phase transfer catalyst. The requirements that the thiocyanate radical in each batch of reaction is excessive by 10% and the yield is high are met, the purpose that the concentration of thiocyanic acid in wastewater is very low is realized, complex wastewater treatment equipment and treatment operation are avoided, and environmental protection pressure is reduced. The preparation method is a green preparation method, and solves the problems of extremely difficult degradation and high biotoxicity of thiocyanate-containing wastewater in conventional isothiocyano compound production. The method is simple to operate and is suitable for industrial production.