Allicin (90percent)

• CAT Number: R054984
• CAS Number: 539-86-6
• Molecular Formula: C6H10OS2
• Molecular Weight: 162.265
• Purity: ≥95%
• Storage: -80°C
• IUPAC Name: 3-prop-2-enylsulfinylsulfanylprop-1-ene
• InChI: InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
• InChIKey: JDLKFOPOAOFWQN-UHFFFAOYSA-N
• SMILES: C=CCSS(=O)CC=C

Allicin (CAS 539-86-6) is a synthetic compound found in garlic that binds nitrogen bases and phosphate backbones in DNA, activates inwardly K-channels, and blocks L-type Ca channels. It has many biological properties such as: inducing autophagy and apoptosis, lowering systolic blood pressure and triglyceride levels. It inhibites the LPS-induced dimerization of TLR4, resulting in the inhibition of NF-kB activation and the expression of COX-2.

Reference

1: Yang D, Lv Z, Zhang H, Liu B, Jiang H, Tan X, Lu J, Baiyun R, Zhang Z. Activation of the Nrf2 Signaling Pathway Involving KLF9 Plays a Critical Role in Allicin Resisting Against Arsenic Trioxide-Induced Hepatotoxicity in Rats. Biol Trace Elem Res. 2017 Mar;176(1):192-200. doi: 10.1007/s12011-016-0821-1. Epub 2016 Aug 25. PubMed PMID: 27561292.
2: Zhong J, Xian D, Xiong X, Liu J. Therapeutic Hotline. Oral allicin in the treatment of Behcet/'s disease through attenuating oxidative stress: A pilot study in 20 patients with mucocutaneous lesions. Dermatol Ther. 2017 Jan;30(1). doi: 10.1111/dth.12429. Epub 2016 Oct 9. PubMed PMID: 27723197.
3: Li S, Chen S, Yang W, Liao L, Li S, Li J, Zheng Y, Zhu D. Allicin relaxes isolated mesenteric arteries through activation of PKA-K(ATP) channel in rat. J Recept Signal Transduct Res. 2017 Feb;37(1):17-24. doi: 10.3109/10799893.2016.1155065. Epub 2016 Apr 6. PubMed PMID: 27049346.
4: Panyod S, Wu WK, Ho CT, Lu KH, Liu CT, Chu YL, Lai YS, Chen WC, Lin YE, Lin SH, Sheen LY. Diet Supplementation with Allicin Protects against Alcoholic Fatty Liver Disease in Mice by Improving Anti-inflammation and Antioxidative Functions. J Agric Food Chem. 2016 Sep 28;64(38):7104-13. doi: 10.1021/acs.jafc.6b02763. Epub 2016 Sep 19. PubMed PMID: 27584700.
5: Yang X, Sha K, Xu G, Tian H, Wang X, Chen S, Wang Y, Li J, Chen J, Huang N. Subinhibitory Concentrations of Allicin Decrease Uropathogenic Escherichia coli (UPEC) Biofilm Formation, Adhesion Ability, and Swimming Motility. Int J Mol Sci. 2016 Jun 29;17(7). pii: E979. doi: 10.3390/ijms17070979. PubMed PMID: 27367677; PubMed Central PMCID: PMC4964365.
6: Chen X, Pang S, Lin J, Xia J, Wang Y. Allicin prevents oxidized low-density lipoprotein-induced endothelial cell injury by inhibiting apoptosis and oxidative stress pathway. BMC Complement Altern Med. 2016 May 20;16:133. doi: 10.1186/s12906-016-1126-9. PubMed PMID: 27207282; PubMed Central PMCID: PMC4875621.
7: Arzanlou M. Inhibition of streptococcal pyrogenic exotoxin B using allicin from garlic. Microb Pathog. 2016 Apr;93:166-71. doi: 10.1016/j.micpath.2016.02.010. Epub 2016 Feb 18. PubMed PMID: 26911644.
8: Müller A, Eller J, Albrecht F, Prochnow P, Kuhlmann K, Bandow JE, Slusarenko AJ, Leichert LI. Allicin Induces Thiol Stress in Bacteria through S-Allylmercapto Modification of Protein Cysteines. J Biol Chem. 2016 May 27;291(22):11477-90. doi: 10.1074/jbc.M115.702308. Epub 2016 Mar 23. PubMed PMID: 27008862; PubMed Central PMCID: PMC4882420.
9: Wang W, Du Z, Nimiya Y, Sukamtoh E, Kim D, Zhang G. Allicin inhibits lymphangiogenesis through suppressing activation of vascular endothelial growth factor (VEGF) receptor. J Nutr Biochem. 2016 Mar;29:83-9. doi: 10.1016/j.jnutbio.2015.11.004. Epub 2015 Nov 24. PubMed PMID: 26895668.
10: Lv R, Mao N, Wu J, Lu C, Ding M, Gu X, Wu Y, Shi Z. Neuroprotective effect of allicin in a rat model of acute spinal cord injury. Life Sci. 2015 Dec 15;143:114-23. doi: 10.1016/j.lfs.2015.11.001. Epub 2015 Nov 3. PubMed PMID: 26546416.
11: El-Kashef DH, El-Kenawi AE, Suddek GM, Salem HA. Protective effect of allicin against gentamicin-induced nephrotoxicity in rats. Int Immunopharmacol. 2015 Dec;29(2):679-86. doi: 10.1016/j.intimp.2015.09.010. Epub 2015 Sep 29. PubMed PMID: 26391062.
12: Jiang X, Zhang Y, Li F, Zhu Y, Chen Y, Yang S, Sun G. Allicin as a possible adjunctive therapeutic drug for stage II oral submucous fibrosis: a preliminary clinical trial in a Chinese cohort. Int J Oral Maxillofac Surg. 2015 Dec;44(12):1540-6. doi: 10.1016/j.ijom.2015.06.015. Epub 2015 Jul 10. PubMed PMID: 26165773.
13: Lin JJ, Chang T, Cai WK, Zhang Z, Yang YX, Sun C, Li ZY, Li WX. Post-injury administration of allicin attenuates ischemic brain injury through sphingosine kinase 2: In vivo and in vitro studies. Neurochem Int. 2015 Oct;89:92-100. doi: 10.1016/j.neuint.2015.07.022. Epub 2015 Aug 12. PubMed PMID: 26275594.
14: Wang H, Li X, Liu X, Shen D, Qiu Y, Zhang X, Song J. Influence of pH, concentration and light on stability of allicin in garlic (Allium sativum L.) aqueous extract as measured by UPLC. J Sci Food Agric. 2015 Jul;95(9):1838-44. doi: 10.1002/jsfa.6884. Epub 2014 Sep 25. PubMed PMID: 25205359.
15: Wilde SC, Keppler JK, Palani K, Schwarz K. β-Lactoglobulin as nanotransporter for allicin: Sensory properties and applicability in food. Food Chem. 2016 May 15;199:667-74. doi: 10.1016/j.foodchem.2015.12.055. Epub 2015 Dec 11. PubMed PMID: 26776023.
16: Wu X, Li X, Song Y, Li H, Bai X, Liu W, Han Y, Xu L, Li J, Zhang D, Wang H, Fan Z. Allicin protects auditory hair cells and spiral ganglion neurons from cisplatin – Induced apoptosis. Neuropharmacology. 2017 Apr;116:429-440. doi: 10.1016/j.neuropharm.2017.01.001. Epub 2017 Jan 3. PubMed PMID: 28062185.
17: Ranjbar-Omid M, Arzanlou M, Amani M, Shokri Al-Hashem SK, Amir Mozafari N, Peeri Doghaheh H. Allicin from garlic inhibits the biofilm formation and urease activity of Proteus mirabilis in vitro. FEMS Microbiol Lett. 2015 May;362(9). pii: fnv049. doi: 10.1093/femsle/fnv049. Epub 2015 Apr 2. PubMed PMID: 25837813.
18: Zhuang J, Li Y, Chi Y. Role of p38 MAPK activation and mitochondrial cytochrome-c release in allicin-induced apoptosis in SK-N-SH cells. Anticancer Drugs. 2016 Apr;27(4):312-7. doi: 10.1097/CAD.0000000000000340. PubMed PMID: 26771864.
19: Abu El Hammed W, Soufy H, El-Shemy A, Nasr SM, Dessouky MI. Use of allicin as feed additive to enhance vaccination capacity of Clostridium perfringens toxoid in rabbits. Vaccine. 2016 Apr 12;34(17):2000-7. doi: 10.1016/j.vaccine.2016.02.073. Epub 2016 Mar 11. PubMed PMID: 26973070.
20: Gruhlke MC, Hemmis B, Noll U, Wagner R, Lühring H, Slusarenko AJ. The defense substance allicin from garlic permeabilizes membranes of Beta vulgaris, Rhoeo discolor, Chara corallina and artificial lipid bilayers. Biochim Biophys Acta. 2015 Apr;1850(4):602-11. doi: 10.1016/j.bbagen.2014.11.020. Epub 2014 Dec 4. PubMed PMID: 25484312.