3386-97-8

Basic information

• Product Name: ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER
• Synonyms: 1-BUTENE-4-ISOTHIOCYANATE;3-BUTEN-1-YL ISOTHIOCYANATE;3-BUTENYL ISOTHIOCYANATE;ISOCYANIC ACID 3-BUTEN-1-YL ESTER;ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER;1-Butene, 4-isothiocyanato-;4-Isothiocyanato-1-butene;Isothiocyanic acid, 3-butenyl ester
• CAS NO: 3386-97-8
• Molecular Formula: C₅H₇NS
• Molecular Weight: 113.18
• EINECS: 222-209-8
• Mol File: 3386-97-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 77 °C / 21mmHg
• Flash Point: 44.2°C
• Appearance: /
• Density: 0.99
• Vapor Pressure: 2.72mmHg at 25°C
• Refractive Index: 1.5210 to 1.5240
• CAS DataBase Reference: ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER(3386-97-8)
• EPA Substance Registry System: ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER(3386-97-8)

Safety Data

• Statements: 36
• Safety Statements: 26
• RIDADR: UN 1992 3/6.1/PG III
• HazardClass: 3/6.1
• PackingGroup: III
• Hazardous Substances Data: 3386-97-8(Hazardous Substances Data)

Usage

Description

ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER is a colorless liquid with a penetrating aroma, commonly found in horseradish, mustard, and wasabi. It has a high strength odor and is recommended to be smelled in a 0.01% solution or less.

Uses

Used in Flavor Industry:
ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER is used as a flavoring agent for its strong and distinctive aroma. It is added to various food products to enhance their flavor and provide a unique taste experience.
Used in Fragrance Industry:
ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER is used as a fragrance ingredient for its penetrating aroma. It is incorporated into perfumes, colognes, and other scented products to create a long-lasting and memorable scent.
Used in Agricultural Industry:
ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER is used as a natural pesticide for its ability to repel insects and pests. It is applied to crops to protect them from damage and ensure a healthy harvest.
Used in Research and Development:
ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER is used as a chemical intermediate in the synthesis of various organic compounds. It is utilized in research and development to create new products and improve existing ones.

InChI:InChI=1/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2

Upstream product

• 3952-98-5 sinigrin 
• 4478-93-7 D,L-sulforaphane 
• 4430-36-8 erucin 
• 6068-89-9 but-3-enyl thiocyanate 
• 463-71-8 thiophosgene 
• 2524-49-4 3-butene-1-amine 
• 75-15-0 carbon disulfide 

Downstream Products

• 33522-07-5 N-(3-butenyl)-N'-phenylthiourea 
• 7472-34-6 N-(β-Methallyl)-acetthionamid 

Relevant articles and documents

Antioxidant activity of two edible isothiocyanates: Sulforaphane and erucin is due to their thermal decomposition to sulfenic acids and methylsulfinyl radicals

Sulforaphane (SFN) and erucin (ERN) are isothiocyanates (ITCs) bearing, respectively, methylsulfinyl and methylsulfanyl groups. Their chemopreventive and anticancer activity is attributed to ability to modulate cellular redox status due to induction of Phase 2 cytoprotective enzymes (indirect antioxidant action) but many attempts to connect the bioactivity of ITCs with their radical trapping activity failed. Both ITCs are evolved from their glucosinolates during food processing of Cruciferous vegetables, therefore, we studied antioxidant behaviour of SFN/ERN at elevated temperature in two lipid systems. Neither ERN nor SFN inhibit the oxidation of bulk linolenic acid (below 100 °C) but both ITCs increase oxidative stability of soy lecithin (above 150 °C). On the basis of GC-MS analysis we verified our preliminary hypothesis (Antioxidants 2020, 9, 1090) about participation of sulfenic acids and methylsulfinyl radicals as radical trapping agents responsible for the antioxidant effect of edible ITCs during thermal oxidation of lipids at elevated temperatures (above 140 °C).

Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard

Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPA1. The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are not known except for a few compounds. To investigate the effect of carbon chain length and substituents of ITCs, the TRPA1-activiting ability of 16 ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency, the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small. (Figure Presented).

THE INTRAMOLECULAR FORMATION OF EPITHIOALKANENITRILES FROM ALKENYLGLUCOSINOLATES BY CRAMBE ABYSSINICA SED FLOUR

Enzymatic degradations of mixtures of potassium 3-butenylglucosinolate and allylglucosinolate by aqueous suspensions of Crambe abyssinica seed flour led to the formation of 4,5-epithiopentanenitrile and essentially unlabelled 3,4-epithiobutanenitrile.The formation of epithioalkanenitriles from alkenylglucosinolates is, therefore deduced to be an intramolecular process. -- Key Word Index - Crambe abyssinica; Cruciferae; allylglucosinolate; 3-butenylglucosinolate; 3,4-epithiobutanenitrile; 4,5-epithiopentanenitrile; sinigrin; episulphide; thiirane; biosynthesis.