Basic information
- Standard SMILES
C=CCSS(=O)CC=C- InChIKey
JDLKFOPOAOFWQN-UHFFFAOYSA-N- Molecular formula
- C6H10OS2
- Average molar mass
- 162.3 g/mol
- Monoisotopic mass
- 162.01730729
Names & identifiers
- Preferred name
- Allicin
- IUPAC
- 3-prop-2-enylsulfinylsulfanylprop-1-ene
- English name
- Allicin
- Molecular formula
- C6H10OS2
- Molecular weight
- 162.27
Names & synonyms
Show more names
Database identifiers
- CAS
539-86-6- PubChem CID
- 65036
- DTXSID
DTXSID6043707- ChEMBL
CHEMBL359965- ChEBI
CHEBI:28411- UNII
- 3C39BY17Y6
- EC Number
- 208-727-7
- Nikkaji
- J71.032F、J816.011B
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 61.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 120
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 25 °C · 25°C
- Boiling point
- 259 °C · 259°C (rough estimate)
- Density
- 420 · d420 1.112
- refractive index
- 20 · nD20 1.561
- storage temp.
- 4 °C, · 4°C, away from moisture and light
- solubility
- 5 mg/mL · DMSO : 5 mg/mL (30.81 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
- form
- liquid
- color
- Colorless to light yellow
- Water Solubility
- 24 g/L · 24g/L(10 ºC)
- 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(S(SCC=C)=O)C=C
- LogP
- 1.133 · 1.133 (est)
- FDA UNII
- 3 C39BY17Y6 · 3C39BY17Y6
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- HS Code
- 29329990 · 29329990
- Toxicity
- 50 in · LD50 in mice (mg/kg): 60 i.v.; 120 s.c. (Cavallito, Bailey)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Safety data
- hs_code
- 29329990
- Toxicity
- LD50 in mice (mg/kg): 60 i.v.; 120 s.c. (Cavallito, Bailey)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Substances which lower blood glucose levels.
Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.
Applications
DescriptionAllicin is one of the major allergens in garlic (Allium sativum L.). It is responsible of the characteristical fiavour of the bulbs.
DescriptionAllicin is a natural product originally isolated from A. sativum that has wide-ranging biological effects including antioxidative, anticancer, antimicrobial, and antifungal activities. It inhibits the cysteine proteases cathepsin B and L, facipain 2, and rhodesain with Ki values of 8.6 and 9.3, 1.04, and 5.31 μM, respectively. It shows antiparasitic activity against P. falciparum (IC50 = 5.2 μM) and T. b. brucei (IC50 = 13.8 μM), the parasites that cause malaria and African sleeping sickness, respectively. Allicin (5-10 μM) dose-dependently inhibits cell adhesion, invasion, and migration in various lung adenocarcinoma cell lines. It also alters the balance of tissue inhibitors of matrix metalloproteinases (TIMPs) and matrix metalloproteinases (MMPs), decreases phosphorylation of Akt, and decreases PI3K/Akt signaling.
HistoryAs the main active substance of garlic, garlic was separated by Cavallito and Bailey in 1944 from crushed garlic. Cavallito firstly clarified the physical properties and chemical structure of the scent of garlic.Fresh garlic does not contain free allicin but only its precursor material alliin. When the garlic undergoes physical mechanical crushing, garlic alliinase is activated and catalyzes the breakdown of alliin into allicin.The reported preparation methods of allicin contain extraction, biosynthesis, and chemical synthesis. Chemical synthesis starts from raw material of diallyldisulfides, m-chloroperoxy benzoic acid to get crude allicin. According to the United States patent report, biosynthesis preparation of allicin comes from natural sources or synthetic, after it is made into a certain concentration of aqueous solution, it is converted into allicin by reaction with alliinase. Extraction of allicin with low boiling nonpolar solvent can acquire pure allicin, but it must be stored at 70°C to prevent from decomposing.
UsesAllicin is naturally formed by the action of the enzyme allicinase on alliin when the tissue of the garlic bulb is disrupted. Allicin shows antibacterial activity.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionAn antibacterial substance extracted from garlic (allium).
Related reactions
Linked notes
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