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Diallyl sulfide

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  • Diallyl sulfide
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  • 2023-08-24
  • CAS:592-88-1
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  • Allyl Sulfide
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  • 2023-02-13
  • CAS:592-88-1
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  • Allyl Sulfide
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  • 2021-08-31
  • CAS:592-88-1
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Diallyl sulfide Basic information
General Description Physical & Chemical Properties Preparation Method Uses Toxicity Maximum limits
Product Name:Diallyl sulfide
Synonyms:(CH2=CHCH2)2S;1-propene,3,3’-thiobis-;3-(Allylsulfanyl)-1-propene;3,3’-thiobis-1-propen;3,3’-thiobis-1-Propene;3-Prop-2-enylsulfanylprop-1-ene;Bis(2-propenyl) sulfide;3-(2-Propenylthio)propan-1-ene
CAS:592-88-1
MF:C6H10S
MW:114.21
EINECS:209-775-1
Product Categories:sulfide Flavor;Allium cepa (Onion);Allium sativum (Garlic);Armoracia rusticana (Horseradish);Building Blocks;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Sulfides/Disulfides;Sulfur Compounds
Mol File:592-88-1.mol
Diallyl sulfide Structure
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)
FEMA 2042 | ALLYL SULFIDE
refractive index n20/D 1.490(lit.)
Fp 115 °F
storage temp. 2-8°C
solubility 3mg/mL in ethanol;5mg/mL in DMSO;10mg/mL in dimethyl formamide
form Liquid
color Clear colorless
Odorat 0.10 % in propylene glycol. sulfurous onion garlic horseradish metallic
Odor Typesulfurous
Odor Threshold0.00022ppm
explosive limit1.1%(V)
Water Solubility Soluble in alcohol, chloroform, ether, and carbon tetrachloride. Insoluble in water.
Merck 14,297
JECFA Number458
BRN 1736016
Dielectric constant4.9(20℃)
InChIKeyUBJVUCKUDDKUJF-UHFFFAOYSA-N
LogP2.61
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
Hazard Codes Xi
Risk Statements 10-36/37/38
Safety Statements 26-36-37/39-23-16
RIDADR UN 1993 3/PG 3
WGK Germany 2
RTECS BC4900000
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29309070
Hazardous Substances Data592-88-1(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Allyl sulfide English
SigmaAldrich English
ACROS English
ALFA English
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.
Diallyl Disulfide
Figure 1: Diallyl Disulfide
Diallyl trisulfide
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
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 PropertiesA colorless liquid with characteristic garlic odor. Oil-soluble component of garlic
Chemical Propertiesclear colorless liquid
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.
UsesDiallyl sulfide is a modulator of drug metabolizing enzyme P450 system and inducer of the phase II detoxifying enzyme GST. Diallyl sulfide is also an inhibitor of CYP2E1 and believed to prevent chemically-induced carcinogenesis in many tissues. It is also used as a food additive. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
DefinitionChEBI: Diallyl sulfide is an organic sulfide.
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
General DescriptionAllyl sulfide is a volatile flavor compound naturally found in Allium species such as garlic and onion. It is has a characteristic garlic odor and is used as a flavoring agent in meat and condiments.
Biochem/physiol ActionsOrganosulfur compound from garlic that inhibits chemically-induced carcinogenesis in experimental animals. Competitive inhibitor of Cytochrome P450 2E1 (CYP2E1) that, in turn, blocks the activation of several chemcal carcinogens.
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
Raw materialsSodium sulfide-->Sodium sulfide nonahydrate-->CAPSAICIN/CAPSICUM-->Garlic P.E
Preparation Productsclopenthixol-->2-METHYL-PENT-4-ENAL-->1,3-Dimercaptopropane-->Diallyldisulfide
Tag:Diallyl sulfide(592-88-1) Related Product Information
Diallylamine Allyl ether Diallyl trisulfide Allyl mercaptan 1,5-HEXADIENE Allyl chloride 2,2'-Thiobisethylamine Dimethyl sulfide Allyl glycidyl ether Sodium sulfide CARBONYL SULFIDE Sodium allylsulfonate Diphenyl sulfide Borane-methyl sulfide complex Allyl bromide Hydrogen Sulfide Allicin Diallyldisulfide, remainder mainly diallyl sulfide,Diallyldisulfide, 70%, remainder mainly diallyl sulfide