AFCDB: 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

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

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

Showing 1 to 10 of 14 entries

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

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Food	Content Range	Average	Reference

Broccoli	Expected but not quantified	Not Available	DUKE
White cabbage	Expected but not quantified	Not Available	DUKE
Bison	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Elk	Expected but not quantified	Not Available	HMDB

Showing 1 to 6 of 6 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti feedant			DUKE
anti mutagenic			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
counterirritant			DUKE
decongestant	77715	A drug used to relieve nasal congestion in the upper respiratory tract.	DUKE
embryotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE

Showing 1 to 10 of 16 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
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
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
mustard	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.
strong	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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

Showing 1 to 6 of 6 entries

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

3-Isothiocyanato-1-propene (FDB012440)

Structure for FDB012440 (3-Isothiocyanato-1-propene)