3-butenyl isothiocyanate
4-isothiocyanatobut-1-ene
Identification
| Name | 3-butenyl isothiocyanate |
| IUPAC | 4-isothiocyanatobut-1-ene |
| CAS Number | 3386-97-8 |
| EINECS | 222-209-8 |
| FDA UNII | 13O98H1EW1 |
| Molecular Formula | C5 H7 N S |
| Molecular Weight | 113.18279000 |
| MDL Number | MFCD00191660 |
| Nikkaji Number | J45.898H |
Regulatory
| JECFA Food Flavoring | 1889 3-butenyl isothiocyanate |
| DG SANTE Food Flavourings | 12.283 3-butenyl isothiocyanate |
| FEMA Number | 4418 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 3386-97-8 ; 3-BUTENYL ISOTHIOCYANATE |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.98500 to 0.98700 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.196 to 8.213 |
| Refractive Index | 1.52100 to 1.52300 @ 20.00 °C. |
| Boiling Point | 163.00 to 164.00 °C. @ 760.00 mm Hg, 75.00 to 77.00 °C. @ 14.00 mm Hg |
| Vapor Pressure | 2.722000 mmHg @ 25.00 °C. (est) |
| Flash Point | 112.00 °F. TCC ( 44.44 °C. ) |
| logP (o/w) | 2.692 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
| Similar Items | note |
Organoleptic Properties
| Odor Description | aromatic pungent |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 3-butenyl isothiocyanate usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 110.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 4000 (μg/person/day) |
| Threshold of Concern | 540 (μg/person/day) |
| baked goods | - |
| beverages(nonalcoholic) | 1.00000 |
| beverages(alcoholic) | 1.00000 |
| breakfast cereal | - |
| cheese | 0.50000 |
| chewing gum | 5.00000 |
| condiments / relishes | 40.00000 |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | 2.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | 0.50000 |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | 0.50000 |
| reconstituted vegetables | - |
| seasonings / flavors | 10.00000 |
| snack foods | 1.00000 |
| soft candy | 2.00000 |
| soups | 1.00000 |
| sugar substitutes | - |
| sweet sauces | - |
| Dairy products, excluding products of category 02.0 (01.0) | 0.10000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 0.10000 |
| Edible ices, including sherbet and sorbet (03.0) | 1.00000 |
| Processed fruit (04.1) | 0.10000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | 0.10000 |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 2.00000 |
| Bakery wares (07.0) | 1.00000 |
| Meat and meat products, including poultry and game (08.0) | 0.10000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 0.10000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 0.10000 |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 10.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 20.00000 |
| Ready-to-eat savouries (15.0) | 0.10000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 0.10000 |
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Potential Uses
Natural Occurrence
Synonyms
3-
buten-1-yl isothiocyanate
1-
butene-4-isothiocyanate
1-
butene, 4-isothiocyanato-
4-iso
thiocyanato-1-butene
4-iso
thiocyanatobut-1-ene
iso
thiocyanic acid 3-buten-1-yl ester
iso
thiocyanic acid but-3-enyl ester
iso
thiocyanic acid butenyl ester
iso
thiocyanic acid, 3-butenyl ester
PubMed:
Generation of the antioxidant yellow pigment derived from 4-methylthio-3-butenyl isothiocyanate in salted radish roots (takuan-zuke).
PubMed:
Flavor, glucosinolates, and isothiocyanates of nau (Cook's scurvy grass, Lepidium oleraceum) and other rare New Zealand Lepidium species.
PubMed:
Mitochondria-mediated apoptosis in human lung cancer A549 cells by 4-methylsulfinyl-3-butenyl isothiocyanate from radish seeds.
PubMed:
GC-MS Analysis of the Extracts from Korean Cabbage (Brassica campestris L. ssp. pekinensis) and Its Seed.
PubMed:
Response surface optimization and identification of isothiocyanates produced from broccoli sprouts.
PubMed:
Effect of pretreatment with dehulling and microwaving on the flavor characteristics of cold-pressed rapeseed oil by GC-MS-PCA and electronic nose discrimination.
PubMed:
Instability and Structural Change of 4-Methylsulfinyl-3-butenyl Isothiocyanate in the Hydrolytic Process.
PubMed:
Chemopreventive effects of 4-methylthio-3-butenyl Isothiocyanate (Raphasatin) but not curcumin against pancreatic carcinogenesis in hamsters.
PubMed:
4-Methylsulfanyl-3-butenyl isothiocyanate derived from glucoraphasatin is a potent inducer of rat hepatic phase II enzymes and a potential chemopreventive agent.
PubMed:
Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables.
PubMed:
Male Phyllotreta striolata (F.) produce an aggregation pheromone: identification of male-specific compounds and interaction with host plant volatiles.
PubMed:
In-silico study of 4-methylsulfinyl-3-butenyl isothiocyanate binding to tubulin induces A549 cells apoptosis.
PubMed:
Hexane extract of Raphanus sativus L. roots inhibits cell proliferation and induces apoptosis in human cancer cells by modulating genes related to apoptotic pathway.
PubMed:
In-vitro free radical scavenging, antiproliferative and anti-zearalenone cytotoxic effects of 4-(methylthio)-3-butenyl isothiocyanate from Tunisian Raphanus sativus.
PubMed:
Semiquantitative analysis of 3-butenyl isothiocyanate to monitor an off-flavor in mustard seeds and glycosinolates screening for origin identification.
PubMed:
Mustard oil in "Shibori Daikon" a variety of Japanese radish, selectively inhibits the proliferation of H-ras-transformed 3Y1 cells.
PubMed:
Isothiocyanate from the Tunisian radish (Raphanus sativus) prevents genotoxicity of Zearalenone in vivo and in vitro.
PubMed:
Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L.
PubMed:
Kaiware Daikon (Raphanus sativus L.) extract: a naturally multipotent chemopreventive agent.
PubMed:
Comparison of the glucosinolate-myrosinase systems among daikon (Raphanus sativus, Japanese white radish) varieties.
PubMed:
Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts.
PubMed:
Aqueous extract from Spanish black radish (Raphanus sativus L. Var. niger) induces detoxification enzymes in the HepG2 human hepatoma cell line.
PubMed:
A Comparison of Semiochemically Mediated Interactions Involving Specialist and Generalist Brassica-feeding Aphids and the Braconid Parasitoid Diaeretiella rapae.
PubMed:
A major factor in gravitropism in radish hypocotyls is the suppression of growth on the upper side of hypocotyls.
PubMed:
Isothiocyanates stimulating oviposition by the diamondback moth, Plutella xylostella.
PubMed:
Raphanus sativus and its isothiocyanates inhibit vascular smooth muscle cells proliferation and induce G(1) cell cycle arrest.
PubMed:
Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro.
PubMed:
Induction of myrosinase gene expression and myrosinase activity in radish hypocotyls by phototropic stimulation.
PubMed:
Simultaneous monitoring of volatile selenium and sulfur species from se accumulating plants (wild type and genetically modified) by GC/MS and GC/ICPMS using solid-phase microextraction for sample introduction.
PubMed:
4-(Methylthio)-3-butenyl isothiocyanate, a principal antimutagen in daikon (Raphanus sativus; Japanese white radish).
PubMed:
Phototropic stimulation induces the conversion of glucosinolate to phototropism-regulating substances of radish hypocotyls.
PubMed:
Isothiocyanates in myrosinase treated herb extract of Cleome chrysantha decne. and their antimicrobial activities.
PubMed:
Thermal degradation of sulforaphane in aqueous solution.
PubMed:
Antimicrobial components of some cruciferae plants (Diplotaxis harra Forsk. and Erucaria microcarpa Boiss.)
PubMed:
Occurrence of stereoisomers of 1-(2'-pyrrolidinethione-3'-yl)- 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in fermented radish roots and their different mutagenic properties.
PubMed:
Herbicidal activity of sulforaphene from stock (Matthiola incana).
PubMed:
Behavioral and electrophysiological responses of Aphids to host and nonhost plant volatiles.
PubMed:
Glucosinolate degradation products, alkanes and fatty acids from plants and cell cultures of Descurainia sophia.
PubMed:
[Isothiocyanate and vinyl thio-oxazolidone contents of rape seeds and rape seed oil].