イソチオシアン酸アリル

Nitrogen Compounds -> Isothiocyanates

Flammable agents - 2nd degree

2.150

2.11

Very pungent

Mustard odor

Acrid taste

Mustard taste

1.0126 at 68 °F (NTP, 1992) - Denser than water; will sink

1.0126 g/cu cm at 20 °C

Relative density (water = 1): 1.0

1.013-1.020

1.013 @ 20°C

less than 0.1 mg/mL at 66 °F (NTP, 1992)

In water, 2,000 mg/L at 20 °C

Very soluble in benzene, ethyl ether, ethanol

Miscible with alcohol and most organic solvents. One mL dissolves 8 mL 70% alcohol

SOLUBILITY IN ALCOHOL: 1:8 IN 80% ETHANOL; COMPLETELY MISCIBLE WITH ETHER, CHLOROFORM, AND BENZENE

Soluble in alcohol, ether, carbon disulfide

115 °F (NTP, 1992)

[ChemIDplus] 46 °C

115 °F (46 °C) (Closed Cup)

46 °C c.c.

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1488) of reports.

Danger

H226 (98.6%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1488 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: 1-Propene, 3-isothiocyanato-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

1-Propene, 3-isothiocyanato- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 3-isothiocyanato- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 22-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/25606

Allyl isothiocyanate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 46 °C explosive vapour/air mixtures may be formed.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

A skin, eye, and respiratory tract irritant; Tear drawing; May cause skin sensitization; May cause liver injury; [ICSC] The vapor is lacrimogenic and can cause keratitis which interferes with vision. [HSDB] Toxic by skin contact and ingestion; A vesicant--causes burns; Lachrymator; May cause pneumonitis and pulmonary edema after inhalation of high concentration; [MSDSonline] Reported occupational adverse effects are cutaneous allergy and severe respiratory tract irritation; Threshold for respiratory irritation is about 4 ppm; [AIHA]

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) /They are/ ... used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Allyl isothiocyanate is included on this list.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Allyl isothiocyanate is included in nasal decongestant drug products.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Allyl isothiocyanate is included in fever blister and cold sore treatment drug products.

DHHS/NTP; Carcinogenesis Bioassay of Allyl Isothiocyanate in F344/N Rats and B6C3F1 Mice (Gavage Study) Technical Report Series No. 234 (1982) NIH Publication No. 83-1790

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Flower and Vegetable Oils, EPA 738-R-93-031 (December 1993). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 29, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

To fight fire, use foam, carbon dioxide, dry chemical.

Safe Storage: Fireproof. Separated from strong oxidants, acids and food and feedstuffs. Well closed. Store only if stabilized.

Containers: 5 lb bottles.

Environmental considerations: Land spill: Dig a pit, pong, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete.

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses.

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.

Evacuate danger area! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Evacuate danger area! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) diet 82000 ppm (95% confidence interval: 66000-103000 ppm)

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 6.9 mg/L, and pH 7.8; Concentration: 85.6 ug/L for 96 hr

LC50; Species: Danio rerio (Zebra Danio) embryo age 4 hr post fertilization, AB strain; Conditions: freshwater, static, 28 °C, pH 6.8-7.0; Concentration: 40-400 ug/L for 20 hr /100% purity/

LC50; Species: Oryzias latipes (Japanese Medaka) juvenile age 28-43 days, weight 18-21 mg; Conditions: freshwater, flow through, 25 °C, pH 7.88, hardness 45.8 (38.0-52.0) mg/L CaCO3, alkalinity 45.9 (35.0-58.5) mg/L CaCO3, dissolved oxygen 6.8 mg/L; Concentration: 77 ug/L for 96 hr (95% confidence interval: 54-109 ug/L) /97.0% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a structure estimation method(2), indicates that allyl isothiocyanate is expected to have moderate mobility in soil(SRC). Volatilization of allyl isothiocyanate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.41X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3.70 mm Hg(3), and water solubility, 2000 mg/L(4). Allyl isothiocyanate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). A mean half-life of 2 days in 6 different soils maintained at 75% moisture capacity and 20 °C was reported for allyl isothiocycanate. When maintained under aerobic conditions, transformation rates were not affected(5), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a structure estimation method(2), indicates that allyl isothiocyanate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.4X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 3.70 mm Hg(4), and water solubility, 2000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6.5 hours and 5 days, respectively(SRC). The estimated volatilization half-life from a model pond is 30 days if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 12(SRC), from an estimated log Kow of 2.15(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A mean half-life of 2 days in 6 different soils maintained at 75% moisture capacity and 20 °C was reported for allyl isothiocycanate. When maintained under aerobic conditions, transformation rates were not affected(10), suggesting that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl isothiocycanate, which has a vapor pressure of 3.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl isothiocycanate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.4 hours, calculated from its rate constant of 9.95X10-11 cu cm/molecule-sec at 25 °C(3). Allyl isothiocycanate does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Alllyl isothiocyanate concentrations in various foods have been reported as follows: shredded cabbage 3 mg/kg; coleslaw 17 mg/kg; and horseradish roots 1.3-1.8 g/kg(1).

REPORTED USE: NON-ALCOHOLIC BEVERAGES 0.02-0.50 PPM; ICE CREAM, ICES, ETC 0.50 PPM; CANDY 0.50 PPM; BAKED GOODS 5.2 PPM; CONDIMENTS 52 PPM; MEATS 87 PPM; SYRUPS 10-88 PPM

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

Inhalation (L96) ; oral (L96) ; dermal (L96)2)

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Allyl isothiocyanate is an allelopathic (inhibits the growth of surrounding plants) secondary matabolite produced by Alliaria petiolata(1), a herbaceous biennial native to Eurasia native and an invasive specie in North America(1,2); also known as garlic mustard(2). In plants, allyl isothiocyanate is formed from the glucosinolate sinigrin(3).

Plants containing allyl isothiocyanate(1).[Table#1723]

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) /They are/ ... used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Allyl isothiocyanate is included on this list.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Allyl isothiocyanate is included in nasal decongestant drug products.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Allyl isothiocyanate is included in fever blister and cold sore treatment drug products.

The insecticide and repellent allyl isothiocyanate is exempt from the requirement of a tolerance for residues when used as a component of food grade oil of mustard, in or on all raw agricultural commodities, when applied according to approved labeling.

Based on the reviews of the generic data for the active ingredients flower and vegetable oils, the Agency has sufficient information on the health effects of flower and vegetable oils and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing flower and vegetable oils for all uses, except the use of essential oils in antimicrobial products, are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Allyl isothiocyanate is found on List D. Case No: 4097; Pesticide type: Insecticide, fungicide, herbicide, rodenticide, antimicrobial; Case Status: RED Approved 01/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): Allyl isothiocyanate; Data Call-in (DCI) Date(s): 02/22/94, 10/13/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

... Here, /investigators have/ shown that AITC arrests human bladder cancer cells in mitosis and also induces apoptosis. Mitotic arrest by AITC was associated with increased ubiquitination and degradation of alpha- and beta-tubulin. AITC directly binds to multiple cysteine residues of the tubulins. AITC induced mitochondrion-mediated apoptosis, as shown by cytochrome c release from mitochondria to cytoplasm, activation of caspase-9 and caspase-3, and formation of TUNEL-positive cells. Inhibition of caspase-9 blocked AITC-induced apoptosis. Moreover, /investigators/ found that apoptosis induction by AITC depended entirely on mitotic arrest and was mediated via Bcl-2 phosphorylation at Ser-70. Pre-arresting cells in G(1) phase by hydroxyurea abrogated both AITC-induced mitotic arrest and Bcl-2 phosphorylation. Overexpression of a Bcl-2 mutant prevented AITC from inducing apoptosis. /Investigators/ further showed that AITC-induced Bcl-2 phosphorylation was caused by c-Jun N-terminal kinase (JNK), and AITC activates JNK. Taken together, this study has revealed a novel anticancer mechanism of a phytochemical that is commonly present in human diet.

In this study, the underlying mechanisms of the potential anti-inflammatory properties of allyl-isothiocyanate (AITC) were analysed in vitro and in vivo. Murine RAW264.7 macrophages stimulated with lipopolysaccharide (LPS) were supplemented with increasing concentrations of AITC. In addition, C57BL/6 mice (n= 10 per group) were fed a pro-inflammatory high-fat diet and AITC was administered orally via gavage for 7 days. Biomarkers of inflammation were determined both in cultured cells and in mice. AITC significantly decreased tumor necrosis factor alpha mRNA levels and its secretion in LPS stimulated RAW264.7 macrophages. Furthermore, gene expression of other pro-inflammatory markers including interleukin-1beta and inducible nitric oxide synthase were down-regulated following AITC treatment. AITC decreased nuclear p65 protein levels, a subunit of the transcription factor NF-?B. Importantly, /this/ data indicates that AITC significantly attenuated microRNA-155 levels in LPS-stimulated RAW264.7 macrophages in a dose-dependent manner. The anti-inflammatory effects of AITC were accompanied by an increase in Nrf2 nuclear translocation and consequently by an increase of mRNA and protein levels of the Nrf2 target gene heme-oxygenase 1. AITC was slightly less potent than sulforaphane (used as a positive control) in down-regulating inflammation in LPS-stimulated macrophages. A significant increase in nuclear Nrf2 and heme-oxygenase 1 gene expression and only a moderate down-regulation of interleukin-1beta and microRNA-155 levels due to AITC was found in mouse liver. Present data suggest that AITC exhibits potent anti-inflammatory activity in cultured macrophages in vitro but has only little anti-inflammatory activity in mice in vivo.

... In this study, AITC was shown to inhibit the proliferation of human metastatic colorectal adenocarcinoma SW620 cells in vitro by inducing cell cycle arrest at the G2/M phase. The signaling pathway of AITC action involved the down-regulation of the pivotal Cdc25B and Cdc25C protein phosphatases in the treated cells. Quantitative real-time PCR of AITC-treated SW620 cells revealed a time-dependent down-regulation of Cdc25B and Cdc25C mRNA levels, which resulted in a decrease in the expression levels of these two proteins. Upon prolonged exposure, AITC induced caspase-mediated apoptosis in SW620 cells. The apoptotic process was evidenced by the activation of initiator caspases (-8 and -9) and effector caspases (-3 and -7), and the cleavage of poly(ADP-ribose) polymerase (PARP). The antitumor activity of AITC was further demonstrated in a SW620 xenograft in vivo. ...

...Little is known regarding the effect of structurally related compounds such as allyl isothiocyanate (AITC), butyl isothiocyanate (BITC) and phenylethyl isothiocyanate (PEITC) on Nrf2 target gene expression. In this study AITC, BITC and PEITC significantly increased phosphorylation of ERK1/2, an upstream target of Nrf2 in NIH3T3 fibroblasts. EKR1/2 phosphorylation was accompanied by an increased nuclear translocation and transactivation of Nrf2. AITC, BITC and PEITC significantly enhanced mRNA and protein levels of the Nrf2 targets gamma-glutamyl cysteine synthetase (gammaGCS), heme oxygenase-1 (HO-1) and NAD(P)H:quinone oxidoreductase (NQO1). HO-1 and gammaGCS both contain CpG islands within their promoter region. However, analysis of DNA methylation status in NIH3T3 cells indicated that expression of these genes may not be dependant on promoter methylation. ...Aliphatic and aromatic isothiocyanates such as AITC, BITC and PEITC induce phase 2 and antioxidant enzymes in cultured fibroblasts.

For more Mechanism of Action (Complete) data for ALLYL ISOTHIOCYANATE (13 total), please visit the HSDB record page.

Four adult volunteers (two men, two women, aged 20-45) ingested 10 g brown mustard with bread, and a control group of four participants ate bread without mustard. In a second experiment, 20 g of brown mustard were eaten in turkey or chicken sandwiches. In both experiments, urine samples were collected at various intervals up to 48 hr following the meal. The major urinary metabolite was N-acetyl-S-(N-allylthiocarbamoyl)- L-cysteine, the N-acetylcysteine conjugate of allyl isothiocyanate, but none was found after 12 hr. Excretion of this metabolite was dose-dependent.

Male and female Fischer 344 rats (8-10 weeks old) and male and female B6C3F1 mice (6-8 weeks old) were given (14)C-allyl isothiocyanate in a solution of ethanol: Emulphor EL-620:water (1:1:8) at doses of 25.2 or 252 umol/kg (2.5 or 25 mg/kg bw) by gavage... The major metabolite detected in rat and mouse urine was the mercapturic acid, N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine, while mouse urine also contained three other major and two minor metabolites. The metabolism of allyl isothiocyanate by male and female rats was similar, but the females excreted more than twice as much urine as the males.

... Allyl isothiocyanate absorbed in vivo is metabolized mainly through the mercapturic acid pathway and excreted in urine. ...

...Rats excreted one major and four minor metabolites in urine. The major metabolite from rat urine was identified by NMR spectroscopy to be the mercapturic acid N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine. Mice excreted in urine the same major metabolite identified in rat urine as well as three other major and two minor metabolites. Sex-related variations were observed in the relative amounts of these metabolites. Both species excreted a single metabolite in feces. Metabolism of AITC by male and female rats was similar, but female rats excreted over twice the urine volume of male rats. Results of the present study indicate that excretion of a more concentrated solution of AITC metabolite(s) in urine may account for the toxic effects of AITC on the bladder of male rats.

... Three radioactive components were found in the urine of mice and two in rats. The three components were inorganic thiocyanate, allylthiocarbamoylmercapturic acid and allylthiocarbamoylcysteine in mice, but no cysteine conjugate was found in rat urine. In the mouse, approximately 80% of the (14)C was present in the urine as the thiocyanate ion whereas in the rat some 75% was as the mercapturate. This indicates that in the mouse, hydrolysis of AITC was the major metabolic pathway whereas in the rat glutathione conjugation was the major route. ...

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

... Bioavailability of allyl isothiocyanate is extremely high, as nearly 90% of orally administered AITC is absorbed. ...

The urine was the major route of excretion of radioactivity (50-80% of dose) following the oral administration (2.5 and 25 mg/kg body weight) of allyl(14)C-isothiocyanate (AITC) to male and female Fischer 344 rats and B6C3F1 mice. Smaller amounts were found in the feces (6-12%) and expired air (3-7%). The major difference between the two species was the greater retention of radioactivity after 4 days within rats (18-24% of dose) when compared with mice (2-5% of dose). ... A species difference was seen in the amount of (14)C-AITC-derived radioactivity present in the whole blood of rats and mice; measurable levels of radioactivity remained within rat blood for a longer time period (up to 240 hr) when compared with mice (96 hr). Examination of the urinary bladders of male and female rats following oral dosing with (14)C-AITC showed a sex difference with greater amounts of (14)C-AITC and/or its metabolites within the bladder tissue of male rats. ...

Male and female Fischer 344 rats (8-10 weeks old) and male and female B6C3F1 mice (6-8 weeks old) were given (14)C-allyl isothiocyanate in a solution of ethanol: Emulphor EL-620:water (1:1:8) at doses of 25.2 or 252 umol/kg (2.5 or 25 mg/kg bw) by gavage, 25 mg/kg bw by injection into a tail vein for studies of distribution ...The radiolabel was cleared primarily in urine (70-80%) and exhaled air (13-15%), with lesser amounts in feces (3-5%) in both species. ... Major sex- and species-related differences in the tissue distribution of allyl isothiocyanate were restricted to the urinary bladder. Thus, the urinary bladder of male rats contained five times higher concentrations of allyl isothiocyanate-derived radiolabel that that of male mice at early time points, but all of the allyl isothiocyanate-derived radiolabel was cleared from male rat bladder by 24 hr.

Used to make flavors and war gases; Used medically as a counterirritant; [ChemIDplus] Used as a fungicide, insecticide fumigant, and a repellent for cats and dogs; Also used in some model airplane cements to deter glue sniffers and externally as a rubefacient; [HSDB] Generally recognized as safe by the FDA as a food additive; Used as an ethanol denaturant; [AIHA]

Photographic Processing [Category: Other]

For allyl isothiocyanate (USEPA/OPP Pesticide Code: 004901) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fumigant, ointments, and mustard plasters.

Table: Reported uses (ppm): (FEMA, 1994) [Table#1725]

Manufacture flavors; war gas

2023: 50,000 - <250,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1976) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#1724]

Allyl isothiocyanate

Allyl isosulfocyanate; Allyl thiocarbonimide; 1-Propenal, 3-isothiocyanato-; 2-Propenyl isothiocyanate; AITC

IFRA_STD_107.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

REACTION OF ALLYL AMINE AND CARBON DISULFIDE IN THE PRESENCE OF MERCURIC CHLORIDE

By distillation of sodium thiocyanate and allyl chloride.

Isolated from Brassica nigra (L.) Koch, Cruciferae (black mustard seed), or prepared from allyl iodide & potassium thiocyanate

Prepared by reaction of allyl bromide with ammonium thiocyanate followed by thermal rearrangement.

... Can be prepared by reacting allyl chloride with alkaline-earth or alkali isothiocyanates.

Outdoor Animal Repellant (Woodstream Corporation), Allyl isothiocyanate 0.2160%, Capsaicin (in oleoresin of capsicum) 0.0420%.

Insect Control Concentrate (Champon Millennium Chemicals, Inc), Allyl isothiocyanate 3.7%, Capsaicin (in oleoresin of capsicum) 0.42%.

Scent-Off Aroma Pouches (Baker's &18 Corporation), Allyl isothiocyanate 0.2000%, Oil of cintronella 1.2000%, Oil of lemongrass 2.000%, Oil of orange 0.0200%, Methyl salicylate 0.0200%, Bergamont oil 0.1100%, alpha-Ionone 0.0100, Geraniol 0.0400%.

Scent-Off Pellets (Baker's &18 Corporation), Allyl isothiocyanate 0.2000%, Oil of cintronella 1.2000%, Oil of lemongrass 2.000%, Oil of orange 0.0200%, Methyl salicylate 0.0200%, Bergamont oil 0.1100%, alpha-Ionone 0.0100, Geraniol 0.0400%.

For more Formulations/Preparations (Complete) data for ALLYL ISOTHIOCYANATE (7 total), please visit the HSDB record page.

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Mining (except Oil and Gas) and support activities

1-Propene, 3-isothiocyanato-: ACTIVE

The seed of sinapsis nigra contains the glycoside, sinigrin, which, in the presence of the enzyme myrosin, decomposes to yield allyl isothiocyanate (volatile oil of mustard)...

May have applications in packaged foods such as meat and meat products ... exhibits negligible goitrogenic activity