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Diallyl Trisulfide

Cat No.:V40474 Purity: ≥98%
Diallyl Trisulfide is extracted from garlic.
Diallyl Trisulfide
Diallyl Trisulfide Chemical Structure CAS No.: 2050-87-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Diallyl Trisulfide is extracted from garlic. Diallyl Trisulfide suppresses the growth of Penicillium expansile (MFC99 value: ≤ 90 μg/mL) and promotes cell apoptosis by producing reactive oxygen species (ROS) and damaging cell ultrastructure, and has anti-cancer capabilities.
Biological Activity I Assay Protocols (From Reference)
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Garlic (Allium sativum) contains alliin, which is metabolized by the enzyme alliinase to allicin, thought to be responsible for most of garlic's medicinal properties and odor. Garlic’s odor in milk is attributed to allyl methyl sulfide. Garlic has been used to lower cholesterol and blood pressure. It has no specific indications for use during lactation in western countries. Garlic has been used as a galactogogue in India and Türkiye, although no good scientific data could be located on its use alone as a galactogogue. Galactogogues should never replace evaluation and counseling on modifiable factors that affect milk production. Garlic has a long history of use as a food and medicine and is "generally recognized as safe" (GRAS) as a food flavoring by the U.S. Food and Drug Administration, including during lactation. Garlic's odor is transmitted to breastmilk, which may increase infant sucking time acutely and might enhance the breastfed infant's food choices in the long term. Some mothers in Türkiye reportedly use garlic to improve the taste and quality of their milk. Limited scientific data found that a few days of oral garlic supplementation caused no adverse effects in nursing mothers or infants. When used as a medicinal, garlic is generally well tolerated in adults, but gastrointestinal side effects and bad breath and body odor may occur. Garlic has anti-platelet effects and should be used cautiously by women at risk for bleeding. Garlic can cause allergies and should be avoided by persons allergic to garlic or other members of the lily family, such as hyacinth, tulip, onion, leek, and chives. Topical application of garlic can cause dermatitis and burns and should be used with caution, especially in infants. One nursing mother received severe burns to the breast from prolonged (2 days) application of a poultice of raw, crushed garlic to treat a self-diagnosed Candida infection.
Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site.
◉ Effects in Breastfed Infants
Maternal garlic ingestion has a reputation for causing colic in breastfed infants. Two papers tend to refute this claim. In one, 153 mothers who answered a questionnaire were no more likely to report colic in their infants in the previous week if they had ingested garlic than if they had not.
In another study, mothers who were given either 1.5 grams of garlic or placebo capsules once daily in a blinded fashion for 3 days were asked if their infants had exhibited any signs of colic (were fussier, cried more or had more gas) after capsule ingestion. Four of 20 women who ingested garlic thought their infants had colic; however, 4 of 10 women who received placebo thought they had received garlic and reported colic in their infants.
◉ Effects on Lactation and Breastmilk
Forty women who complained of an insufficient milk supply at 5 days postpartum were given a combination herbal supplement as 2 capsules of Lactare (Pharma Private Ltd., Madras, India) 3 times daily. Each capsule contained wild asparagus 200 mg, ashwagandha (Withania somnifera) 100 mg, fenugreek 50 mg, licorice 50 mg, and garlic 20 mg. By day 4 of therapy, no infants required supplementary feeding. Infants were weighed before and after each feeding on the fifth day of maternal therapy to determine the amount of milk ingested. On the day of the test weighing, infants' milk intake averaged 388 mL, and the fluid and caloric intake was considered adequate. This study cannot be considered as valid evidence of a galactogogue effect of these herbs because it lacks randomization, blinding, a placebo control, and maternal instruction in breastfeeding technique. Additionally, infants were breastfed only 6 to 8 times daily, which is insufficient to maximize milk supply.
In two studies conducted by the same investigators, capsules containing 1.5 g of garlic extract (General Nutrition Center, Pittsburgh, PA) were given to nursing mothers. In the first experiment, 8 mothers receive a garlic capsule or placebo once daily in a crossover fashion. Garlic-naive infants whose mothers ingested garlic capsules spent more time (33 vs 27 minutes) attached to the nipple during the time period of 1.5 to 3 hours after garlic ingestion when garlic odor in milk was maximal than in those whose mothers received a placebo; however, total number of nursings or total amount of milk ingestion did not differ between groups. A study randomized nursing mothers to receive garlic capsules or placebo for 3 days before testing with a single capsule as in the study above. Infants who received garlic in the milk for the first time spent 30% more time nursing than after placebo. Infants who had been previously exposed to garlic in milk, did not spend more time nursing after subsequent garlic exposure in milk. The authors interpreted the results of these studies as having a positive effect on infants' later food choices (i.e., being less "picky" about foods).
References

[1]. Diallyl trisulfide induces apoptosis and inhibits proliferation of A549 cells in vitro and in vivo. Acta Biochim Biophys Sin (Shanghai). 2012 Jul;44(7):577-83.

[2]. Diallyl trisulfide inhibits naphthalene-induced oxidative injury and the production of inflammatory responses in A549 cells and mice. Int Immunopharmacol. 2015 Dec;29(2):326-333.

[3]. Antiviral activity of diallyl trisulfide against H9N2 avian influenza virus infection in vitro and in vivo. Virol J. 2021 Aug 19;18(1):171.

[4]. Diallyl trisulfide (DATS) effectively induced apoptosis of postharvest diseasePenicillium expansum of citrus. Annals of Microbiology. December 2009, Volume 59, Issue 4, pp 675-679.

Additional Infomation
Diallyl trisulfide is an organic trisulfide that is trisulfane in which both of the hydrogens are replaced by allyl groups. A component of the essential oil of garlic and a major component of the traditional Chinese medicine allitridium, it exhibits antifungal, antitumour and antioxidant activity It has a role as an apoptosis inducer, an estrogen receptor antagonist, an antineoplastic agent, a vasodilator agent, an antioxidant, an anti-inflammatory agent, an insecticide, an antiprotozoal drug, a platelet aggregation inhibitor and an antilipemic drug.
Diallyl trisulfide has been reported in Allium ursinum, Allium victorialis, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H10S3
Molecular Weight
178.3386
Exact Mass
177.994
CAS #
2050-87-5
PubChem CID
16315
Appearance
Colorless to light yellow liquid
Density
1.1±0.1 g/cm3
Boiling Point
229.5±43.0 °C at 760 mmHg
Flash Point
87.8±25.2 °C
Vapour Pressure
0.1±0.4 mmHg at 25°C
Index of Refraction
1.582
LogP
4.59
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
6
Heavy Atom Count
9
Complexity
70.4
Defined Atom Stereocenter Count
0
SMILES
S(C([H])([H])C([H])=C([H])[H])SSC([H])([H])C([H])=C([H])[H]
InChi Key
UBAXRAHSPKWNCX-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2
Chemical Name
3-(prop-2-enyltrisulfanyl)prop-1-ene
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~560.73 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (14.02 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (14.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (14.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.6073 mL 28.0363 mL 56.0727 mL
5 mM 1.1215 mL 5.6073 mL 11.2145 mL
10 mM 0.5607 mL 2.8036 mL 5.6073 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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