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Details

Stereochemistry RACEMIC
Molecular Formula C6H10OS2
Molecular Weight 162.2754
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLICIN

SMILES

C=CCSS(=O)CC=C

InChI

InChIKey=JDLKFOPOAOFWQN-UHFFFAOYSA-N
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2

HIDE SMILES / InChI

Molecular Formula C6H10OS2
Molecular Weight 162.2754
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of an allicin-based product on cryptosporidiosis in neonatal calves.
1998 Apr 1
Modulation of TNF-alpha-induced ICAM-1 expression, NO and H2O2 production by alginate, allicin and ascorbic acid in human endothelial cells.
2003 Mar
Quantitative determination of allicin in garlic: supercritical fluid extraction and standard addition of alliin.
2004 Feb 25
In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity.
2004 Jul-Aug
Pungent products from garlic activate the sensory ion channel TRPA1.
2005 Aug 23
The pungency of garlic: activation of TRPA1 and TRPV1 in response to allicin.
2005 May 24
Allicin-induced suppression of Mycobacterium tuberculosis 85B mRNA in human monocytes.
2007 Apr 6
4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
2007 Aug 14
Contractile effect of TRPA1 receptor agonists in the isolated mouse intestine.
2007 Dec 8
Induction of total insensitivity to capsaicin and hypersensitivity to garlic extract in human by decreased expression of TRPV1.
2007 Jan 10
A dietary agonist of transient receptor potential cation channel V3 elicits endothelium-dependent vasodilation.
2010 Apr
In vitro investigation of antifungal activity of allicin alone and in combination with azoles against Candida species.
2010 Apr
Effect of traditional Chinese medicinal herbs on Candida spp. from patients with HIV/AIDS.
2011 Apr
Comparison between efficacy of allicin and fluconazole against Candida albicans in vitro and in a systemic candidiasis mouse model.
2011 Feb
Allicin alleviates inflammation of trinitrobenzenesulfonic acid-induced rats and suppresses P38 and JNK pathways in Caco-2 cells.
2015
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:35:29 UTC 2021
Edited
by admin
on Sat Jun 26 10:35:29 UTC 2021
Record UNII
3C39BY17Y6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALLICIN
MI   WHO-DD  
Systematic Name English
ALLICIN [MI]
Common Name English
ALLICIN [WHO-DD]
Common Name English
S-2-PROPEN-1-YL 2-PROPENE-1-SULFINOTHIOATE
Systematic Name English
ALLICIN (CONSTITUENT OF GARLIC) [DSC]
Common Name English
S-ALLYL PROP-2-ENE-1-SULFINOTHIOATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C68520
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
DSLD 2437 (Number of products:54)
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
Code System Code Type Description
FDA UNII
3C39BY17Y6
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
EPA CompTox
539-86-6
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
NCI_THESAURUS
C68521
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
MESH
C006452
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
MERCK INDEX
M1523
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
208-727-7
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
DRUG BANK
DB11780
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
CAS
539-86-6
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
WIKIPEDIA
ALLICIN
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
EVMPD
SUB33584
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
PUBCHEM
65036
Created by admin on Sat Jun 26 10:35:29 UTC 2021 , Edited by admin on Sat Jun 26 10:35:29 UTC 2021
PRIMARY
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