Showing Compound 3-Isothiocyanato-1-propene (FDB012440)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:10 UTC

Update date

2019-11-26 03:06:47 UTC

Primary ID

FDB012440

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Isothiocyanato-1-propene

Description

Chief constituent of natural mustard oiland is also found in cooked cabbage, horseradish, etc. Flavouring ingredient. Potential nutriceutical Allyl isothiocyanate is a volatile organic compound. Allyl isothiocyanate (AITC) is a constituent of mustard, horseradish and wasabi and certain vegetables found in the human diet, mostly in cruciferous vegetables. AITC is a colorless to pale yellow liquid that is slightly soluble in water, but well soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and also is a modulator of enzymes involved in metabolism of xenobiotics, including carcinogens. It is plausible that the wide consumption of dietary AITC may have profound effects on human health. oxidative DNA damage may play important roles in carcinogenic processes induced by AITC. Allergic contact dermatitis from AICT is well known but infrequently reported. AITC is occasionally found as a volatile component of normal human biofluids. (PMID: 5556886, 8222057, 8000299, 10754276, 15373848); Allyl isothiocyanate is mildly toxic with LD50 of 151 mg/kg but is a dangerous lachrymator.

CAS Number

57-06-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Propenyl isothiocyanate	ChEBI
3-Isothiocyanato-1-propene	ChEBI
AIT	ChEBI
AITC	ChEBI
Allyl isosulfocyanate	ChEBI
Allyl mustard oil	ChEBI
Allylsenfoel	ChEBI
Isothiocyanate d'allyle	ChEBI
Isothiocyanic acid allyl ester	ChEBI
Mustard oil	ChEBI
Oil OF mustard	ChEBI
Oleum sinapis	ChEBI
Senf oel	ChEBI
Volatile mustard oil	ChEBI
Volatile oil OF mustard	ChEBI
2-Propenyl isothiocyanic acid	Generator
Allyl isosulfocyanic acid	Generator
Allyl isosulphocyanate	Generator
Allyl isosulphocyanic acid	Generator
Isothiocyanic acid d'allyle	Generator
Isothiocyanate allyl ester	Generator
Allyl isothiocyanic acid	Generator
3-iso-Thiocyanatoprop-1-ene	HMDB
3-Isothiocyanatoprop-1-ene	HMDB
Allyl isothiocyanate (natural)	HMDB
Allyl isothiocyanate non-perfume grade	HMDB
Allyl sevenolum	HMDB
Allylsenevol	HMDB, MeSH
Allylsevenolum	HMDB
Allyspol	HMDB
Artificial mustard oil	HMDB
Carbospol	HMDB
Caswell no. 027	HMDB
FEMA no. 2034	HMDB
Isothiocyansaeureallylester	HMDB
Oleum sinapis volatile	HMDB
Redskin	HMDB
Senfoel	HMDB
Synthetic mustard oil	HMDB
1-Propene, 3-isothiocyanato-	biospider
3-isothiocyanatoprop-1-ene	biospider
3-isothiocyanatopropene	biospider
AITK	biospider
Allyl isorhodanide	biospider
Allyl isothiocyanate	biospider
Allyl isothiocyanate (usp)	biospider
Allyl isothiocyanate [usan]	biospider
Allyl isothiocyanate, inhibited	biospider
Allyl isothiocyanate, non-perfume grade	biospider
Allyl isothiocyanate, stabilized [UN1545] [Poison]	biospider
Allyl isothiocyanate, USAN	db_source
Allyl thiocarbonimide	biospider
Allyl thioisocyanate	biospider
Allylisothiokyanat	biospider
Allyspol 75EC	db_source
Artificial oil of mustard	biospider
Brassica seed oil	biospider
Essential oils, mustard	biospider
Fats and glyceridic oils, mustard	biospider
FEMA 2034	db_source
Isothiocyanato-1-propene	biospider
Isothiocyanic acid, allyl ester	biospider
Isothiocyanic acid,allyl ester	biospider
Mustard essential oils	biospider
Mustard oil (van)	biospider
Mustard oil, volatile	biospider
Mustard oil, volatile, synthetic	biospider
Mustard seed oil	biospider
Mustard, brown (brassica SPP.)	biospider
Mustard, yellow (brassica SPP.)	biospider
Oil of mustard	biospider
Oil of mustard BPC 1949	biospider
Oil of mustard, artificial	biospider
Oil of mustard, expressed	biospider
Oils, brassica alba	biospider
Oils, brassica nigra	biospider
Oils, essential, mustard	biospider
Oils, glyceridic, mustard	biospider
Oils, mustard	biospider
Ol eum sinapis volatile	biospider
Potassium allyl isothiocyanate	biospider
Potassium, (1-isothiocyanato-2-propenyl)-	biospider
Propene, 3-isothiocyanato-	biospider
Propenyl isothiocyanate	biospider
Senf oel (german)	biospider
Senfoel (german)	biospider
Volatile oil of mustard	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.9	ALOGPS
logP	1.8	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	30.49 m³·mol⁻¹	ChemAxon
Polarizability	10.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H5NS

IUPAC name

3-isothiocyanatoprop-1-ene

InChI Identifier

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

InChI Key

ZOJBYZNEUISWFT-UHFFFAOYSA-N

Isomeric SMILES

C=CCN=C=S

Average Molecular Weight

99.154

Monoisotopic Molecular Weight

99.014269855

Classification

Description

Belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Isothiocyanates

Sub Class

Not Available

Direct Parent

Isothiocyanates

Alternative Parents

Substituents

Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

isothiocyanate (CHEBI:73224 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Respiratory, thoracic and mediastinal disorders:

Apnea

Nervous system disorders:

Seizure

Psychiatric disorders:

Confusion

Ear and labyrinth disorders:

Vertigo

General disorders and administration site conditions:

Pain

Cardiac disorders:

Cardiac arrest

Gastrointestinal disorders:

Vomiting

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant

Role

Biological role:

Metabolite

Industrial application:

Household products:

Antimicrobial agent

Pharmaceutical industry:

Antineoplastic agent:

Antitumor

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 48.45%; H 5.08%; N 14.13%; S 32.34%	DFC
Melting Point	Fp -80°	DFC
Boiling Point	Bp12 44°	DFC
Experimental Water Solubility	2 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d154 1.02	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000e-9000000000-69a4920e3d464262cd5f	2014-09-20	View Spectrum
GC-MS	3-Isothiocyanato-1-propene, non-derivatized, GC-MS Spectrum	splash10-000e-9000000000-74e6764518eaef9083ea	Spectrum
GC-MS	3-Isothiocyanato-1-propene, non-derivatized, GC-MS Spectrum	splash10-000e-9000000000-74e6764518eaef9083ea	Spectrum
Predicted GC-MS	3-Isothiocyanato-1-propene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-e5da626a3f0a9112da7f	Spectrum
Predicted GC-MS	3-Isothiocyanato-1-propene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0005-9000000000-52a42150ed565c57dd63	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-f39db8b3315f05512c4e	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000l-9000000000-fd8f23ba9a99d3b95b60	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-000e-9000000000-c10457306477602160fd	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3900000000-6f00e6c8cbe246d39e05	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-dc72ed6e7c7c177d9abf	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ccb9e34efa3fbf3caebb	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-a31fab83b72890b37d9e	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-9000000000-ac309b871ff92649f3d1	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6a8f7896b2956a540af4	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-6900000000-c391badfd4188e78a822	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-87228e1d22765d017b75	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-605088af905285399996	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-9aace16230ba7be259d5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05843

CRC / DFC (Dictionary of Food Compounds) ID

HGX19-J:HGX19-J

EAFUS ID

111

Dr. Duke ID

ALLYL-ISOTHIOCYANATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

57-06-7

GoodScent ID

rw1002981

SuperScent ID

Not Available

Wikipedia ID

Allyl isothiocyanate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Eafus: 2618

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Counterirritant		An agent that induces mild irritation or inflammation in one area to reduce discomfort and/or inflammation in another, often used to relieve pain, reduce swelling, and promote healing in conditions like arthritis, sprains, and strains.	DUKE
Decongestant	77715	An agent that reduces nasal congestion by constricting blood vessels, decreasing swelling in the nasal passages. Therapeutically, it relieves sinus pressure and eases breathing, commonly used to treat colds, allergies, and sinusitis.	DUKE
Embryotoxic	52209	An agent that is toxic to embryos, causing harm or malformation during fetal development. Its biological role is to induce teratogenic effects, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Insectiphile	24852	A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration.	DUKE
Mutagenic		An agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.	DUKE
Nematiovistat		A nematode statin, inhibiting nematode growth and development, with therapeutic applications in treating parasitic worm infections, and key medical uses in managing diseases such as river blindness and elephantiasis.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Spice		A plant-derived substance used for flavoring, coloring, or preserving food. Biologically, spices have antimicrobial properties. Therapeutically, they have anti-inflammatory, antioxidant, and digestive applications. Key medical uses include	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sulfur	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pungent	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
garlic	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
strong	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mustard	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755