AllicinA compound that exhibits antimicrobial, antioxidant, antiproliferative activity

Allicin (CAS 539-86-6)

Allicin | CAS 539-86-6 is rated 5.0 out of 5 by 1.
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Synonym: Diallyl thiosulfinate; Allylthiosulphinic acid allyl ester
Application: A compound that exhibits antimicrobial, antioxidant, antiproliferative activity
CAS Number: 539-86-6
Purity: ≥98%
Molecular Weight: 162.27
Molecular Formula: C6H10OS2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Allicin, an active compound of garlic, is unstable in aqueous solution without formic acid. It rapidly decomposes mainly to diallyl sulfide (DAS), diallyl disulfide (DADS), diallyl trisulfide (DATS), and ajoene. DATS and DADS act as donors of H2S donors, which plays a cell signaling role similar to NO and CO. Allicin exhibits antimicrobial, antioxidant, antiproliferative, chemopreventive, antihyperlipidaemic and antihypertensive effects. Additionally, allicin inhibits telomerase activity and inducible nitric oxide synthase (iNOS; NOS II) expression and promotes apoptosis.


References

1. Ankri, S., et al., 1997. Allicin from garlic strongly inhibits cysteine proteinases and cytopathic effects of Entamoeba histolytica. Antimicrobial agents and chemotherapy. 41(10): 2286-8. PMID: 9333064

2. Dirsch, V M., et al., 1998. Effect of allicin and ajoene, two compounds of garlic, on inducible nitric oxide synthase. Atherosclerosis. 139(2): 333-9. PMID: 9712340

3. Ankri, S., et al., 1999. Antimicrobial properties of allicin from garlic. Microbes and infection / Institut Pasteur. 1(2): 125-9. PMID: 10594976

4. Elkayam, A., et al., 2001. The effects of allicin and enalapril in fructose-induced hyperinsulinemic hyperlipidemic hypertensive rats. American journal of hypertension. 14(4 Pt 1): 377-81. PMID: 11336185

5. Hirsch, K., et al., 2000. Effect of purified allicin, the major ingredient of freshly crushed garlic, on cancer cell proliferation. Nutrition and cancer. 38(2): 245-54. PMID: 11525603

6. Sun, Li., et al., 2003. Effects of allicin on both telomerase activity and apoptosis in gastric cancer SGC-7901 cells. World journal of gastroenterology : WJG. 9(9): 1930-4. PMID: 12970878

7. Oommen, Suby., et al., 2004. Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. European journal of pharmacology. 485(1-3): 97-103. PMID: 14757128

8. Cutler, R R., et al., 2004. Antibacterial activity of a new, stable, aqueous extract of allicin against methicillin-resistant Staphylococcus aureus. British journal of biomedical science. 61(2): 71-4. PMID: 15250668

9. Davis, Stephen R., et al., 2005. An overview of the antifungal properties of allicin and its breakdown products--the possibility of a safe and effective antifungal prophylactic. Mycoses. 48(2): 95-100. PMID: 15743425

10. Chung, Lip Yong., et al., 2006. The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide. Journal of medicinal food. 9(2): 205-13. PMID: 16822206

11. Gardner, Christopher D., et al., 2007. Effect of raw garlic vs commercial garlic supplements on plasma lipid concentrations in adults with moderate hypercholesterolemia: a randomized clinical trial. Archives of internal medicine. 167(4): 346-53. PMID: 17325296

12. Benavides, Gloria A., et al., 2007. Hydrogen sulfide mediates the vasoactivity of garlic. Proceedings of the National Academy of Sciences of the United States of America. 104(46): 17977-82. PMID: 17951430

13. El-Kashef, D.H. et al. 2015. Int. Immunopharmacol. 29(2): 679-686. PMID: 26391062

Formulation :
supplied in a Methanol: H2O: Formic acid (60:40:0.1) solution at a concentration of 10mg/mL
Physical State :
Liquid
Solubility :
Soluble in chloroform, water (slightly), alcohol, ether, and benzene.
Storage :
Store at -80° C
Melting Point :
25° C
Boiling Point :
262.21° C (Predicted)
Refractive Index :
n20D 1.56
IC50 :
Induction of apoptosis: IC50 = 20 nM (B-CLL cells); Plasmodium falciparum: IC50 = 5.21 µM; HL-60: IC50 = 5.5 µM (human); Plasmodium berghei: IC50 = 6.8 µM; Trypanosoma brucei brucei: IC50 = 13.8 µM
Ki Data :
Rhodesain: Ki= 5.31 µM (Trypanosoma brucei rhodesiense); cathepsin B: Ki= 8.6 µM (human); cathepsin L: Ki= 9.3 µM (human)
pK Values :
pKa: -7.86 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
65036
MDL Number :
MFCD00468100
EC Number :
208-727-7
SMILES :
C=CCSS(=O)CC=C

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Certificate of Analysis

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Allicin  Product Citations

See how others have used Allicin. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 30537531  Dwivedi, VP.|Bhattacharya, D.|Singh, M.|Bhaskar, A.|Kumar, S.|Fatima, S.|Sobia, P.|Kaer, LV.|Das, G.| et al. 2018. J Ethnopharmacol. 243: 111634.

PMID: # 28693193  Huang, L. et al. 2017. Oncol Lett. 14: 468-474.

Citations 1 to 2 of 2 total

Ratio of which measure do you mean? Volume or concentration?

Asked by: Narges
This product is an aqueous solution (with 0.1 % formic acid as a stabilizer) of allicin at 10 mg/mL.
Answered by: Technical Support
Date published: 2019-11-06

What do you mean with Methanol, H2O, Formic acid (60:40:0.1). Is this procent?

Asked by: Narges
Thank you for your question. I am not sure what you are asking, but I assume you are asking about the ratio. It's a solution with ~60 parts Methanol, ~40 parts Water and 0.1 parts Formic acid.
Answered by: Tech Service
Date published: 2019-10-31

What is the solubility of this product?

Asked by: hawkeye11
This chemical, Allicin (CAS 539-86-6), is supplied in a Methanol: H2O: Formic acid (60:40:0.1) solution at a concentration of 10mg/mL. Allicin itself is miscible in alcohol.
Answered by: Chemical Support 1
Date published: 2018-06-01

Is this product HPLC grade?

Asked by: hawkeye11
This chemical, Allicin (CAS 539-86-6), is not specified as HPLC grade?
Answered by: Chemical Support 1
Date published: 2017-03-29

Is Allicin supplied with a stabilizing reagent present in solution?

Asked by: ChemSynth123
Thank you for your question. The compound, sc-202449, is provided in solution with formic acid, which acts as a stabilizer. But, the storage temperature of -80ºC plays a more crucial role in preventing the decomposition of the compound. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-03-31
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Rated 5 out of 5 by from El El-Kashef, DH. et al. (PubMed 26391062) reported that Allicin exhibited a protective effect against gentamicin-induced nephrotoxicity in rats. -SCBT Publication Review
Date published: 2015-02-07
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