Basic information General Description Physical & Chemical Properties Preparation Method Uses Toxicity Maximum limits Safety Related Supplier
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Diallyl sulfide

Basic information General Description Physical & Chemical Properties Preparation Method Uses Toxicity Maximum limits Safety Related Supplier
Diallyl sulfide Basic information
Diallyl sulfide Chemical Properties
  • Melting point:-83 °C
  • Boiling point:138 °C(lit.)
  • Density 0.887 g/mL at 25 °C(lit.)
  • vapor density 3.9 (vs air)
  • vapor pressure 7 mm Hg ( 20 °C)
  • refractive index n20/D 1.490(lit.)
  • Flash point:115 °F
  • storage temp. 2-8°C
  • form Liquid
  • color Clear colorless
  • explosive limit1.1%(V)
  • Water Solubility Soluble in alcohol, chloroform, ether, and carbon tetrachloride. Insoluble in water.
  • Merck 14,297
  • JECFA Number458
  • BRN 1736016
  • CAS DataBase Reference592-88-1(CAS DataBase Reference)
  • NIST Chemistry Reference1-Propene, 3,3'-thiobis-(592-88-1)
  • EPA Substance Registry System1-Propene, 3,3'-thiobis-(592-88-1)
Safety Information
Diallyl sulfide Usage And Synthesis
  • General DescriptionDiallyl sulfide refers to the following 4 ingredients: diallyl monosulfide, diallyl disulfide, diallyl trisulfide and diallyl tetrasulfide, which exist in putrefaction decomposer of vegetables, green onion and the fruit of.cruciferous plants. As the main component of garlic extract, it is featured with strong anti-cancer, anti-virus, antibacterial activity, strong inhibition of platelet aggregation and immunity improvement. It has been widely used in the industries such as medical and health, fodder and the like.
  • Physical & Chemical PropertiesIt is an oily substance scented with garlic. Boiling point: 139 ° C (101.056Pa), relative density: 0.8876, refractive index: 1.4877. Soluble in organic solvents such as ether and the like, insoluble in water. Also it can be oxidized to diallyl sulfone. Figure 1: Diallyl Disulfide Figure 2: Diallyl trisulfide
  • Preparation MethodThe two main methods for preparation of diallyl sulfide are: biological extraction and chemical synthesis.
    • Biological extraction
    The more common biological extraction methods are steam distillation, organic solvent extraction and supercritical CO2 extraction. Steam distillation is to use water as a solvent, then heat under a certain pressure to extract the soluble active ingredients from the natural products. The advantage of this method is that it is simple to operate and suitable for the extraction of active ingredients that are generally easier to extract. Its disadvantages include the greater loss of the active ingredients in the thermosensitives, lower yield, and that the active ingredients in the extract are not easily separated.
    Process for allicin extraction: fermentation temperature:  50 ~ 55 ℃, fermentation duration: 2h ~ 3h, add water into the garlic with the proportion of 1: 4 water, distilled for the duration of 1.5h ~ 2h.
    Organic solvent extraction method is to use organic solvent as extraction agent, and extract the active ingredients of natural products at a certain temperature and extraction duration.  Usually methanol, ethanol, acetone, ethyl ether or the mixture of these solvents are used as the organic solvents. Compared withthe steam distillation extraction, the advantage of the organic solvent extraction is that the extract has higher purity. Also it is one of the traditional extraction methods.
    Use ethanol with volume fraction of 95% as the extraction solvent, and add the extractant in proportion of 1g: 4mL. First the enzymolysis time was 0.5h when the temperature is set to 40 ℃; then have the extraction for 1.5h when the temperature is set to 30 ℃; finally set the temperature at 50 ℃, and have it concentrated under reduced pressure in a steamer rotating at a speed of 4500r / min to extract allicin. The extraction rate can reach 0.24%.
    • Chemical synthesis
    Mix Na2S2O3•5H2O62g (0.25mol) and 3-bromopropene 24g (0.20mol) in ethanol - water (V ethanol: V water = 60:40) evenly and reflux to homogeneity. Add 30mL of concentrated hydrochloric acid, reflux for 5h, standing still, then separate the upper layer and put it into 100mL10% NaOH solution placed in an ice bath, add 80mL of 25% K3Fe (CN) 6 (6mmol) aqueous solution while stirring and stop after 2.5h. Separate the organic layer and dry it over anhydrous sodium sulfate. Then filter off the desiccant, recover the solvent, and finally 6.6 g of pale yellow oily substance will be obtained. 
    Figure 3: Synthetic route
  • UsesUsed as a reagent. 
    Used in the industries such as medical and health, fodder and the like.
  • ToxicityGRAS(FEMA)。
  • Maximum limitsFEMA (mg / kg): Drinks 0.04; Cold Drink 0.06; Confectionery 0.07; Bakery Products 0.05; Seasoning 13; Meat 3.7.
    FDA, § 172.515: Appropriate amount.
  • Chemical Propertiesclear colorless liquid
  • Chemical PropertiesA colorless liquid with characteristic garlic odor. Oil-soluble component of garlic
  • OccurrenceReported found in garlic (Allium sativum L.), onion (Allium cepa L.), nira (Allium tuberosum Rottl.), caucas (Allium victoralis L.), mustard (Brassica species) and cooked/boiled beef
  • Usesantibacterial, antifungal, antineoplastic, antihypercholesterolaemic, hepatoprotectant
  • Usesmanufacture of flavors.
  • PreparationFrom allyl iodide plus potassium sulfide in alcoho
  • Aroma threshold valuesDetection at 0.05 ppb
  • Taste threshold valuesTaste characteristics at 2 ppm: sulfureous, onion–garlic and vegetative radish-like with a slightly hot nuance
  • Anticancer ResearchIt is a thioether, found in garlic, inhibits cytochrome P450 IIE1 isoform, and therebysuppresses carcinogenesis (Aggarwal and Shishodia 2004). The consumption ofgarlic provides protection from gastrointestinal cancers and also suppresses theprogression of colorectal adenomas (Hosseini and Ghorbani 2015).
Diallyl sulfide Preparation Products And Raw materials
Diallyl sulfide(592-88-1)Related Product Information
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