Allyl isothiocyanate

Names
Preferred IUPAC name

3-Isothiocyanatoprop-1-ene

Other names

Synthetic mustard oil

Identifiers

CAS Number

* 57-06-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:73224 N

ChEMBL |

* ChEMBL233248 Y

ChemSpider |

* 21105854 Y

EC Number |

* 200-309-2

IUPHAR/BPS

* 2420

KEGG |

* D02818 Y
* C19317

PubChem CID

* 5971

RTECS number |

* NX8225000

UNII |

* BN34FX42G3 Y

UN number | 1545

InChI

* InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Y

Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N Y

* InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

Key: ZOJBYZNEUISWFT-UHFFFAOYAS

SMILES

* C=CCN=C=S

Properties

Chemical formula

| C4H5NS
Molar mass | 99.15 g·mol−1
Density | 1.013–1.020 g/cm3
Melting point |  −102 °C (−152 °F; 171 K)
Boiling point |  148 to 154 °C (298 to 309 °F; 421 to 427 K)
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H226, H301, H310, H315, H319, H330, H335, H410

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P320, P321

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels.[1][2][3] It is slightly soluble in water, but more soluble in most organic solvents.[4]

## Contents

* 1 Biosynthesis and biological functions
* 2 Production and applications
* 3 Safety
* 3.1 Oncology
* 4 See also
* 5 References

## Biosynthesis and biological functions

Allyl isothiocyanate can be obtained from the seeds of black mustard (Rhamphospermum nigrum) or brown Indian mustard (Brassica juncea). When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate.[5] This serves the plant as a defense against herbivores; since it is harmful to the plant itself,[6] it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal. Human appreciation of the pungency is learned.[7]: 105

The compound has been shown to strongly repel fire ants (Solenopsis invicta).[8] AITC vapor is also used as an antimicrobial and shelf life extender in food packaging.[7]: 118–120

## Production and applications

Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate:[4]

CH2=CHCH2Cl + KSCN → CH2=CHCH2NCS + KCl

The product obtained in this fashion is sometimes known as synthetic mustard oil. Allyl thiocyanate isomerizes to the isothiocyanate:[9]

2=CHCH
2SCN → CH
2=CHCH
2NCS

Allyl isothiocyanate can also be liberated by dry distillation of the seeds. The product obtained in this fashion is known as volatile oil of mustard.

It is used principally as a flavoring agent in foods. Synthetic allyl isothiocyanate is used as an insecticide, as an anti-mold agent [10] bacteriocide,[11] and nematicide, and is used in certain cases for crop protection.[4] It is also used in fire alarms for the deaf.[12][13]

Hydrolysis of allyl isothiocyanate gives allylamine.[14]

## Safety

Allyl isothiocyanate has an LD50 of 151 mg/kg and is a lachrymator (similar to tear gas or mace).[4]

### Oncology

Based on in vitro experiments and animal models, allyl isothiocyanate exhibits many of the desirable attributes of a cancer chemopreventive agent.[15]

## See also

* Mustard plaster, traditional home remedy
* Piperine, the piquant chemical in black pepper
* Capsaicin, the piquant chemical in chili peppers
* Allicin, the piquant flavor chemical in raw garlic

## References

1. ↑ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Dewachter, I.; van Leuven, F. et al. (2011). "The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil". Current Biology 21 (4): 316–321. doi:10.1016/j.cub.2011.01.031. PMID 21315593. Bibcode: 2011CBio...21..316E.
2. ↑ Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. (2008). "Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor". Toxicology and Applied Pharmacology 231 (2): 150–156. doi:10.1016/j.taap.2008.04.005. PMID 18501939. Bibcode: 2008ToxAP.231..150B.
3. ↑ Ryckmans, T. et al. (2011). "Design and Pharmacological Evaluation of PF-4840154, a Non-Electrophilic Reference Agonist of the TrpA1 Channel". Bioorganic & Medicinal Chemistry Letters 21 (16): 4857–4859. doi:10.1016/j.bmcl.2011.06.035. PMID 21741838.
4. ↑ 4.0 4.1 4.2 4.3 Romanowski, F.; Klenk, H.. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_749.
5. ↑ Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels (2020). "Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants". Phytochemistry 169. doi:10.1016/j.phytochem.2019.112100. PMID 31771793. Bibcode: 2020PChem.169k2100B.
6. ↑ Li, Yingbin; Lu, Daqing; Xia, Yan; Xu, Xinjing; Huang, Huichuan; Mei, Xinyue; Yang, Min; Li, Jianqiang et al. (2023-09-30). "Effects of allyl isothiocyanate fumigation on medicinal plant root knot disease control, plant survival, and the soil bacterial community". BMC Microbiology 23 (1): 278. doi:10.1186/s12866-023-02992-w. ISSN 1471-2180. PMID 37775764. "Allyl isothiocyanate (AITC) [...] has been used in agriculture because of its fungicidal [...] bactericidal, nematocidal [able to destroy nematodes], and herbicidal [able to destroy plants] biological activities.".
7. ↑ 7.0 7.1 Melton, Laurence, ed (2019). The Encyclopedia of Food Chemistry. Netherlands: Elsevier. ISBN 978-0-12-814045-1.
8. ↑ Hashimoto, Yoshiaki; Yoshimura, Masashi; Huang, Rong-Nan (2019). "Wasabi versus red imported fire ants: Preliminary test of repellency of microencapsulated allyl isothiocyanate against Solenopsis invicta (Hymenoptera: Formicidae) using bait traps in Taiwan". Applied Entomology and Zoology 54 (2): 193–196. doi:10.1007/s13355-019-00613-5. Bibcode: 2019AppEZ..54..193H. https://oist.repo.nii.ac.jp/?action=repository_uri&item_id=1557.
9. ↑ Emergon, David W. (1971). "The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment". Journal of Chemical Education 48 (1): 81. doi:10.1021/ed048p81. Bibcode: 1971JChEd..48...81E.
10. ↑ US Patent No. 8691042
11. ↑ Masuda, Shuichi; Masuda, Hideki; Shimamura, Yuko; Sugiyama, Chitose; Takabayashi, Fumiyo (April 2017). "Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori". Natural Product Communications 12 (4): 595–598. doi:10.1177/1934578X1701200431. PMID 30520603.
12. ↑ US patent 20100308995A1, Hideaki Goto, Tomo Sakai, Koichiro Mizoguchi, Yukinobu Tajima, Makoto Imai, "Odor generation alarm and method for informing unusual situation", issued 2015-06-24
13. ↑ Phillipson, Tacye (29 August 2018). "Why would you want a wasabai fire alarm?". https://blog.nms.ac.uk/2018/08/29/why-would-you-want-a-wasbai-fire-alarm/.
14. ↑ Leffler, M. T. (1938). "Allylamine". Organic Syntheses 18: 5. http://www.orgsyn.org/demo.aspx?prep=CV2P0024. ;  Collective Volume, 2, pp. 24
15. ↑ Zhang, Y (2010). "Allyl isothiocyanate as a cancer chemopreventive phytochemical". Molecular Nutrition & Food Research 54 (1): 127–35. doi:10.1002/mnfr.200900323. PMID 19960458.

* v
* t
* e

Cruciferous biochemistry

Types of compounds|

* Phenylthiocarbamide (PTC/PTU)
* Thiocyanates
* Nitriles
* Indoles
* Gibberellin

Glucosinolates|

* Glucobrassicin
* Glucocapparin
* Glucoraphanin
* Gluconasturtiin
* Glucotropaeolin
* Progoitrin
* Sinigrin
* Sinalbin

Isothiocyanates (ITC, mustard oils)|

* Sulforaphane (SFN)
* Raphanin
* Allyl isothiocyanate (AITC)
* Methyl isothiocyanate (MITC)
* Benzyl isothiocyanate (BITC)
* Fluorescein isothiocyanate (FITC)
* Phenyl isothiocyanate (PITC)
* Phenethyl isothiocyanate (PEITC)
* 6-MITC

Bioactive metabolites|

* Goitrin
* Indole-3-carbinol

* Brassicaceae (Cruciferous vegetables): Brassica
* Raphanus
* Cruciferous Biochemistry
* genera (list)

* v
* t
* e

TRP channel modulators

TRPA|

| Activators|

* 4-Hydroxynonenal
* 4-Oxo-2-nonenal
* 4,5-EET
* 12S-HpETE
* 15-Deoxy-Δ12,14-prostaglandin J2
* α-Sanshool (ginger, Sichuan and melegueta peppers)
* Acrolein
* Allicin (garlic)
* Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
* AM404
* Bradykinin
* Cannabichromene (cannabis)
* Cannabidiol (cannabis)
* Cannabigerol (cannabis)
* Cinnamaldehyde (cinnamon)
* CR gas (dibenzoxazepine; DBO)
* CS gas (2-chlorobenzal malononitrile)
* Curcumin (turmeric)
* Dehydroligustilide (celery)
* Diallyl disulfide
* Dicentrine (Lindera spp.)
* Farnesyl thiosalicylic acid
* Formalin
* Gingerols (ginger)
* Hepoxilin A3
* Hepoxilin B3
* Hydrogen peroxide
* Icilin
* Isothiocyanate
* Ligustilide (celery, Angelica acutiloba)
* Linalool (Sichuan pepper, thyme)
* Methylglyoxal
* Methyl salicylate (wintergreen)
* N-Methylmaleimide
* Nicotine (tobacco)
* Oleocanthal (olive oil)
* Paclitaxel (Pacific yew)
* Paracetamol (acetaminophen)
* PF-4840154
* Phenacyl chloride
* Polygodial (Dorrigo pepper)
* Shogaols (ginger, Sichuan and melegueta peppers)
* Tear gases
* Tetrahydrocannabinol (cannabis)
* Thiopropanal S-oxide (onion)
* Umbellulone (Umbellularia californica)
* WIN 55,212-2

|

Blockers|

* Dehydroligustilide (celery)
* Nicotine (tobacco)
* Ruthenium red

TRPC|

| Activators|

* Adhyperforin (St John's wort)
* Diacyl glycerol
* GSK1702934A
* Hyperforin (St John's wort)
* Substance P

|

Blockers|

* DCDPC
* DHEA-S
* Flufenamic acid
* GSK417651A
* GSK2293017A
* Meclofenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* Niflumic acid
* Pregnenolone sulfate
* Progesterone
* Pyr3
* Tolfenamic acid

TRPM|

| Activators|

* ADP-ribose
* BCTC
* Calcium (intracellular)
* Cold
* Coolact P
* Cooling Agent 10
* CPS-369
* Eucalyptol (eucalyptus)
* Frescolat MGA
* Frescolat ML
* Geraniol
* Hydroxycitronellal
* Icilin
* Linalool
* Menthol (mint)
* PMD 38
* Pregnenolone sulfate
* Rutamarin (Ruta graveolens)
* Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
* Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
* Thio-BCTC
* WS-3
* WS-12
* WS-23

|

Blockers|

* Capsazepine
* Clotrimazole
* DCDPC
* Elismetrep
* Flufenamic acid
* Meclofenamic acid
* Mefenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* Nicotine (tobacco)
* Niflumic acid
* Ruthenium red
* Rutamarin (Ruta graveolens)
* Tolfenamic acid
* TPPO

TRPML|

| Activators|

* MK6-83
* PI(3,5)P2
* SF-22

|

TRPP|

| Activators|

* Triptolide (Tripterygium wilfordii)

|

Blockers|

* Ruthenium red

TRPV|

| Activators|

* 2-APB
* 5',6'-EET
* 9-HODE
* 9-oxoODE
* 12S-HETE
* 12S-HpETE
* 13-HODE
* 13-oxoODE
* 20-HETE
* α-Sanshool (ginger, Sichuan and melegueta peppers)
* Allicin (garlic)
* AM404
* Anandamide
* Bisandrographolide (Andrographis paniculata)
* Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil)<!--TRPV1 and TRPV3-->
* Cannabidiol (cannabis)
* Cannabidivarin (cannabis)
* Capsaicin (chili pepper)
* Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
* DHEA
* Diacyl glycerol
* Dihydrocapsaicin (chili pepper)
* Estradiol
* Eugenol (basil, clove)
* Evodiamine (Euodia ruticarpa)
* Gingerols (ginger)
* GSK1016790A
* Heat
* Hepoxilin A3
* Hepoxilin B3
* Homocapsaicin (chili pepper)
* Homodihydrocapsaicin (chili pepper)
* Incensole (incense)
* Lysophosphatidic acid
* Low pH (acidic conditions)
* Menthol (mint)
* N-Arachidonoyl dopamine
* N-Oleoyldopamine
* N-Oleoylethanolamide
* Nonivamide (PAVA) (PAVA spray)
* Nordihydrocapsaicin (chili pepper)
* Paclitaxel (Pacific yew)
* Paracetamol (acetaminophen)
* Phorbol esters (e.g., 4α-PDD)
* Piperine (black pepper, long pepper)
* Polygodial (Dorrigo pepper)
* Probenecid
* Protons
* RhTx
* Rutamarin (Ruta graveolens)
* Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
* Shogaols (ginger, Sichuan and melegueta peppers)
* Tetrahydrocannabivarin (cannabis)
* Thymol (thyme, oregano)
* Tinyatoxin (Euphorbia resinifera/pooissonii)
* Tramadol
* Vanillin (vanilla)
* Zucapsaicin

|

Blockers|

* α-Spinasterol (Vernonia tweediana)
* AMG-517
* Asivatrep
* BCTC
* Cannabigerol (cannabis)
* Cannabigerolic acid (cannabis)
* Cannabigerovarin (cannabis)
* Cannabinol (cannabis)
* Capsazepine
* DCDPC
* DHEA
* DHEA-S
* Flufenamic acid
* GRC-6211
* HC-067047
* Lanthanum
* Mavatrep
* Meclofenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* NGD-8243
* Niflumic acid
* Pregnenolone sulfate
* RN-1734
* RN-9893
* Ruthenium red
* SB-705498
* Tivanisiran
* Tolfenamic acid

See also: Receptor/signaling modulators • Ion channel modulators

* v
* t
* e

Xenobiotic-sensing receptor modulators

CAR|

* Agonists: 6,7-Dimethylesculetin
* Amiodarone
* Artemisinin
* Benfuracarb
* Carbamazepine
* Carvedilol
* Chlorpromazine
* Chrysin
* CITCO
* Clotrimazole
* Cyclophosphamide
* Cypermethrin
* DHEA (prasterone)
* Efavirenz
* Ellagic acid
* Griseofulvin
* Methoxychlor
* Mifepristone
* Nefazodone
* Nevirapine
* Nicardipine
* Octicizer
* Permethrin
* Phenobarbital
* Phenytoin
* Pregnanedione (5β-dihydroprogesterone)
* Reserpine
* TCPOBOP
* Telmisartan
* Tolnaftate
* Troglitazone
* Valproic acid

* Antagonists: 3,17β-Estradiol
* 3α-Androstanol
* 3α-Androstenol
* 3β-Androstanol
* 17-Androstanol
* AITC
* Ethinylestradiol
* Meclizine
* Nigramide J
* Okadaic acid
* PK-11195
* S-07662
* T-0901317

PXR|

* Agonists: 17α-Hydroxypregnenolone
* 17α-Hydroxyprogesterone
* Δ4-Androstenedione
* Δ5-Androstenediol
* Δ5-Androstenedione
* AA-861
* Allopregnanediol
* Allopregnanedione (5α-dihydroprogesterone)
* Allopregnanolone (brexanolone)
* Alpha-Lipoic acid
* Ambrisentan
* AMI-193
* Amlodipine besylate
* Antimycotics
* Artemisinin
* Aurothioglucose
* Bile acids
* Bithionol
* Bosentan
* Bumecaine
* Cafestol
* Cephaloridine
* Cephradine
* Chlorpromazine
* Ciglitazone
* Clindamycin
* Clofenvinfos
* Chloroxine
* Clotrimazole
* Colforsin
* Corticosterone
* Cyclophosphamide
* Cyproterone acetate
* Demecolcine
* Dexamethasone
* DHEA (prasterone)
* DHEA-S (prasterone sulfate)
* Dibunate sodium
* Diclazuril
* Dicloxacillin
* Dimercaprol
* Dinaline
* Docetaxel
* Docusate calcium
* Dodecylbenzenesulfonic acid
* Dronabinol
* Droxidopa
* Eburnamonine
* Ecopipam
* Enzacamene
* Epothilone B
* Erythromycin
* Famprofazone
* Febantel
* Felodipine
* Fenbendazole
* Fentanyl
* Flucloxacillin
* Fluorometholone
* Griseofulvin
* Guggulsterone
* Haloprogin
* Hetacillin potassium
* Hyperforin
* Hypericum perforatum (St John's wort)
* Indinavir sulfate
* Lasalocid sodium
* Levothyroxine
* Linolenic acid
* LOE-908
* Loratadine
* Lovastatin
* Meclizine
* Metacycline
* Methylprednisolone
* Metyrapone
* Mevastatin
* Mifepristone
* Nafcillin
* Nicardipine
* Nicotine
* Nifedipine
* Nilvadipine
* Nisoldipine
* Norelgestromin
* Omeprazole
* Orlistat
* Oxatomide
* Paclitaxel
* Phenobarbital
* Piperine
* Plicamycin
* Prednisolone
* Pregnanediol
* Pregnanedione (5β-dihydroprogesterone)
* Pregnanolone
* Pregnenolone
* Pregnenolone 16α-carbonitrile
* Proadifen
* Progesterone
* Quingestrone
* Reserpine
* Reverse triiodothyronine
* Rifampicin
* Rifaximin
* Rimexolone
* Riodipine
* Ritonavir
* Simvastatin
* Sirolimus
* Spironolactone
* Spiroxatrine
* SR-12813
* Suberoylanilide
* Sulfisoxazole
* Suramin
* Tacrolimus
* Tenylidone
* Terconazole
* Testosterone isocaproate
* Tetracycline
* Thiamylal sodium
* Thiothixene
* Thonzonium bromide
* Tianeptine
* Troglitazone
* Troleandomycin
* Tropanyl 3,5-dimethulbenzoate
* Zafirlukast
* Zeranol

* Antagonists: Ketoconazole
* Sesamin

See also
Receptor/signaling modulators
Nuclear receptor modulators

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Allyl isothiocyanate. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Allyl_isothiocyanate&oldid=4032811"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H301]: Toxic if swallowed
*[H310]: Fatal in contact with skin
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H330]: Fatal if inhaled
*[H335]: May cause respiratory irritation
*[H410]: Very toxic to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P262]: Do not get in eyes, on skin, or on clothing
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P284]: Wear respiratory protection
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P302+350]: IF ON SKIN: Gently wash with soap and water
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P320]: Specific treatment is urgent (see … on this label)
*[P321]: Specific treatment (see … on this label)
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[TRP]: Transient receptor potential
*[TRPA]: Transient receptor potential ankyrin channel
*[TRPC]: Transient receptor potential canonical channel
*[TRPM]: Transient receptor potential melastatin channel
*[TRPML]: Transient receptor potential mucolipin channel
*[TRPP]: Transient receptor potential polycystin channel
*[TRPV]: Transient receptor potential vanilloid channel
*[CAR]: Constitutive androstane receptor
*[PXR]: Pregnane X receptor