592-88-1 Usage
General Description
Different sources of media describe the General Description of 592-88-1 differently. You can refer to the following data:
1. Diallyl 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.
2. Allyl 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.
Physical & Chemical Properties
It 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 Method
The 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
Uses
Different sources of media describe the Uses of 592-88-1 differently. You can refer to the following data:
1. Used as a reagent.?
Used in the industries such as medical and health, fodder and the like.
2. Diallyl 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.
3. antibacterial, antifungal, antineoplastic, antihypercholesterolaemic, hepatoprotectant
4. manufacture of flavors.
Toxicity
GRAS(FEMA)。
Maximum limits
FEMA (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 Properties
Different sources of media describe the Chemical Properties of 592-88-1 differently. You can refer to the following data:
1. A colorless liquid with characteristic garlic odor. Oil-soluble component of garlic
2. clear colorless liquid
Occurrence
Reported 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
Preparation
From allyl iodide plus potassium sulfide in alcoho
Aroma threshold values
Detection at 0.05 ppb
Taste threshold values
Taste characteristics at 2 ppm: sulfureous, onion–garlic and vegetative radish-like with a slightly hot nuance
Biochem/physiol Actions
Organosulfur 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 Research
It 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).
Check Digit Verification of cas no
The CAS Registry Mumber 592-88-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 2 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 592-88:
(5*5)+(4*9)+(3*2)+(2*8)+(1*8)=91
91 % 10 = 1
So 592-88-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2
592-88-1Relevant articles and documents
Regioselective reactions of sulfur, selenium and tellurium chlorides with allyl trimethyl silane
Martynov, Alexander V.,Makhaeva, Natalia A.,Larina, Lyudmila I.,Amosova, Svetlana V.
, p. 1964 - 1968 (2011)
Electrophilic addition of SCl2, SeCl2 and SeCl 4 to 2 equivalents of allyl trimethyl silane proceeds regioselectively to give bis[2-chloro-3-(trimethylsilyl)propyl] sulfide, selenide and selenium dichloride, respectively. The reaction with TeCl 4 affords only diallyl tellurium dichloride. The structures of the compounds were confirmed by 1H, 13C, 77Se and 125Te NMR techniques.
Yb(iii)-catalysedsyn-thioallylation of ynamides
Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 7521 - 7524 (2021/08/05)
Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
Efficient reduction of sulfoxides with NaHSO3 catalyzed by I2
Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moradi, Zahra
, p. 6610 - 6613 (2015/11/09)
An efficient method for the deoxygenation of sulfoxides into their corresponding sulfides at room temperature using NaHSO3 in the presence of catalytic I2 has been reported.
NaI/silica sulfuric acid as an efficient reducing system for deoxygenation of sulfoxides in poly ethylene glycol (PEG-200)
Zarei, Morteza,Ameri, Mohammad Aghil,Jamaleddini, Azar
, p. 259 - 263 (2013/08/26)
Deoxygenation of structurally diverse sulfoxides including dialkyl, diaryl, aryl alkyl and allyl sulfoxides to the corresponding sulfides were carried out using a NaI/silica sulfuric acid reducing system at room temperature in poly ethylene glycol (PEG-200) in excellent yields.
