hexyl isothiocyanate
1-isothiocyanatohexane
Identification
| Name | hexyl isothiocyanate |
| IUPAC | 1-isothiocyanatohexane |
| CAS Number | 4404-45-9 |
| EINECS | 224-549-2 |
| FDA UNII | 2S7C3GA0Z5 |
| Molecular Formula | C7 H13 N S |
| Molecular Weight | 143.25261000 |
| MDL Number | MFCD00014445 |
| Nikkaji Number | J117.065A |
| Beilstein | 1748295 |
Regulatory
| JECFA Food Flavoring | 1895 hexyl isothiocyanate |
| FEMA Number | 4422 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 6803-40-3 ; HEXYL ISOTHIOCYANATE |
Physical Properties
| Appearance | colorless to yellow clear liquid (est) |
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.93100 to 0.94100 @ 20.00 °C. |
| Pounds per Gallon - (est). | 7.756 to 7.839 |
| Refractive Index | 1.49000 to 1.49400 @ 20.00 °C. |
| Boiling Point | 218.00 to 219.00 °C. @ 760.00 mm Hg, 72.00 to 73.00 °C. @ 8.00 mm Hg |
| Vapor Pressure | 0.261000 mmHg @ 25.00 °C. (est) |
| Flash Point | 187.00 °F. TCC ( 86.11 °C. ) |
| logP (o/w) | 3.681 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
| Similar Items | note |
Organoleptic Properties
| Odor Description | sharp green |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | subcutaneous-rabbit LD50 100 mg/kg |
| 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 hexyl isothiocyanate usage levels up to | not for fragrance use. |
| baked goods | - |
| beverages(nonalcoholic) | 1.00000 |
| beverages(alcoholic) | 1.00000 |
| breakfast cereal | - |
| cheese | 0.50000 |
| chewing gum | 5.00000 |
| condiments / relishes | 1.00000 |
| 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 | - |
| reconstituted vegetables | - |
| seasonings / flavors | 5.00000 |
| snack foods | 0.50000 |
| soft candy | 2.00000 |
| soups | 0.50000 |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
hexane, 1-isothiocyanato-
1-
hexyl isothiocyanate
N-
hexyl mustard
hexyl mustard oil
N-
hexyl mustard oil
N-
hexylisothiocyanate
1-iso
thiocyanatohexane
iso
thiocyanic acid hexyl ester
iso
thiocyanic acid, hexyl ester
1-iso
thiocyanohexane
PubMed:
Effect of Wasabi Component 6-(Methylsulfinyl)hexyl Isothiocyanate and Derivatives on Human Pancreatic Cancer Cells.
PubMed:
Intracellular accumulation of structurally varied isothiocyanates correlates with inhibition of nitric oxide production in proinflammatory stimuli-activated tumorigenic macrophage-like cells.
PubMed:
Utilization of 6-(methylsulfinyl)hexyl isothiocyanate for sensitization of tumor cells to antitumor agents in combination therapies.
PubMed:
Homology modeling and structural analysis of human P-glycoprotein.
PubMed:
Molecular Mechanisms Underlying Anti-Inflammatory Actions of 6-(Methylsulfinyl)hexyl Isothiocyanate Derived from Wasabi (Wasabia japonica).
PubMed:
Isothiocyanates from Wasabia japonica activate transient receptor potential ankyrin 1 channel.
PubMed:
Dynamics of Nrf2 and Keap1 in ARE-mediated NQO1 expression by wasabi 6-(methylsulfinyl)hexyl isothiocyanate.
PubMed:
Glutathione biosynthesis via activation of the nuclear factor E2-related factor 2 (Nrf2)--antioxidant-response element (ARE) pathway is essential for neuroprotective effects of sulforaphane and 6-(methylsulfinyl) hexyl isothiocyanate.
PubMed:
Glycogen synthase kinase-3β inhibition of 6-(methylsulfinyl)hexyl isothiocyanate derived from wasabi (Wasabia japonica Matsum).
PubMed:
Microarray-based determination of anti-inflammatory genes targeted by 6-(methylsulfinyl)hexyl isothiocyanate in macrophages.
PubMed:
Alkyl isothiocyanates suppress epidermal growth factor receptor kinase activity but augment tyrosine kinase activity.
PubMed:
Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity.
PubMed:
The augmenting activity of 6-(methylsulfinyl)hexyl isothiocyanate on cellular glutathione levels is less sensitive to thiol compounds than its cytotoxic activity.
PubMed:
Detection of 6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) and its conjugate with N-acetyl-L-cysteine (NAC) by high performance liquid chromatograpy-atmospheric pressure chemical ionization mass spectrometry (HPLC-MS/APCI).
PubMed:
[Experiment study of PHI on histone methylation and acetylation in Molt-4 cells].
PubMed:
Effects of 6-(methylsulfinyl)hexyl isothiocyanate on cyclooxygenase-2 expression induced by lipopolysaccharide, interferon-gamma and 12-O-tetradecanoylphorbol-13-acetate.
PubMed:
Preventive effect of oral administration of 6-(methylsulfinyl)hexyl isothiocyanate derived from wasabi (Wasabia japonica Matsum) against pulmonary metastasis of B16-BL6 mouse melanoma cells.
PubMed:
Inhibition of lipopolysaccharide-induced cyclooxygenase-2 transcription by 6-(methylsulfinyl) hexyl isothiocyanate, a chemopreventive compound from Wasabia japonica (Miq.) Matsumura, in mouse macrophages.
PubMed:
6-(Methylsulfinyl)hexyl isothiocyanate suppresses inducible nitric oxide synthase expression through the inhibition of Janus kinase 2-mediated JNK pathway in lipopolysaccharide-activated murine macrophages.
PubMed:
Selective sensitivity to wasabi-derived 6-(methylsulfinyl)hexyl isothiocyanate of human breast cancer and melanoma cell lines studied in vitro.
PubMed:
Effects of dietary chemopreventive phytochemicals on P-glycoprotein function.
PubMed:
Augmented gene expression of quinone reductase by 6-(methylsulfinyl)hexyl isothiocyanate through avoiding its cytotoxicity.
PubMed:
Transcriptional regulation of nicotinamide adenine dinucleotide phosphate: quinone oxidoreductase in murine hepatoma cells by 6-(methylsufinyl)hexyl isothiocyanate, an active principle of wasabi (Eutrema wasabi Maxim).
PubMed:
Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice.
PubMed:
Formate assay in body fluids: application in methanol poisoning.