Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C6H10OS2 |
| Molecular Weight | 162.273 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][S+](CC=C)SCC=C
InChI
InChIKey=JDLKFOPOAOFWQN-UHFFFAOYSA-N
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
| Molecular Formula | C6H10OS2 |
| Molecular Weight | 162.273 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Allicin (diallylthiosulfinate) is a defence molecule from garlic (Allium sativum L.) with a broad range of biological activities. Allicin is produced upon tissue damage from the non-proteinogenic amino acid alliin (S-allylcysteine sulfoxide) in a reaction that is catalyzed by the enzyme alliinase. Allicin is known to be hydrophobic and can be readily absorbed through the cell membrane without inducing any damage to the phospholipid bilayer and then rapidly metabolized to exert pharmacological effects. The majority of allicin's effects are believed to be mediated via redox-dependent mechanisms. Allicin is physiologically active in microbial, plant and mammalian cells. In a dose-dependent manner allicin can inhibit the proliferation of both bacteria and fungi or kill cells outright, including antibiotic-resistant strains like methicillin-resistant Staphylococcus aureus (MRSA). In plants allicin inhibits seed germination and attenuates root-development. Furthermore, in mammalian cell lines, including cancer cells, allicin induces cell-death and inhibits cell proliferation. Allicin was found to provide cardio-protective effects by inducing vasorelaxation and alleviating various pathological conditions of CVD, including cardiac hypertrophy, angiogenesis, platelet aggregation, hyperlipidemia and hyperglycemia. Allicin was also discovered to further protect the cardiovascular system by enhancing the antioxidant status by lowering the level of reactive oxygen species and stimulating the production of glutathione.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Allicin alleviates inflammation of trinitrobenzenesulfonic acid-induced rats and suppresses P38 and JNK pathways in Caco-2 cells. | 2015 |
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| Effect of traditional Chinese medicinal herbs on Candida spp. from patients with HIV/AIDS. | 2011-04 |
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| Comparison between efficacy of allicin and fluconazole against Candida albicans in vitro and in a systemic candidiasis mouse model. | 2011-02 |
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| A dietary agonist of transient receptor potential cation channel V3 elicits endothelium-dependent vasodilation. | 2010-04 |
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| In vitro investigation of antifungal activity of allicin alone and in combination with azoles against Candida species. | 2010-04 |
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| Contractile effect of TRPA1 receptor agonists in the isolated mouse intestine. | 2007-12-08 |
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| 4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1. | 2007-08-14 |
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| Allicin-induced suppression of Mycobacterium tuberculosis 85B mRNA in human monocytes. | 2007-04-06 |
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| Induction of total insensitivity to capsaicin and hypersensitivity to garlic extract in human by decreased expression of TRPV1. | 2007-01-10 |
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| Pungent products from garlic activate the sensory ion channel TRPA1. | 2005-08-23 |
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| The pungency of garlic: activation of TRPA1 and TRPV1 in response to allicin. | 2005-05-24 |
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| In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity. | 2004-07-22 |
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| Quantitative determination of allicin in garlic: supercritical fluid extraction and standard addition of alliin. | 2004-02-25 |
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| Modulation of TNF-alpha-induced ICAM-1 expression, NO and H2O2 production by alginate, allicin and ascorbic acid in human endothelial cells. | 2003-03 |
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| Effects of an allicin-based product on cryptosporidiosis in neonatal calves. | 1998-04-01 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:08:20 GMT 2025
by
admin
on
Mon Mar 31 19:08:20 GMT 2025
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| Record UNII |
3C39BY17Y6
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| Record Status |
Validated (UNII)
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| Record Version |
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Systematic Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68520
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DSLD |
2437 (Number of products:54)
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| Code System | Code | Type | Description | ||
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3C39BY17Y6
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28411
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DTXSID6043707
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C68521
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C006452
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m1523
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208-727-7
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DB11780
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539-86-6
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100000127530
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ALLICIN
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SUB33584
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65036
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allicin
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admin on Mon Mar 31 19:08:20 GMT 2025 , Edited by admin on Mon Mar 31 19:08:20 GMT 2025
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (HPLC)
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