Allicin

HCID 65036CAS 539-86-6

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

Allicin539-86-6Diallyl thiosulfinateThio-2-propene-1-sulfinic acid S-allyl esterAllylthiosulphinic acid allyl ester3-prop-2-enylsulfinylsulfanylprop-1-ene2-Propene-1-sulfinothioic acid S-2-propenyl esterDTXSID60437073C39BY17Y6CHEBI:284113-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene3-((prop-2-ene-1-sulfinyl)sulfanyl)prop-1-ene
Show more names
Allitridgarlic mealAlliMedalliosanC6H10S2OAllisatinARICINE(P)ALLICIN(SH)Allicin 10%
RefChem:5523DTXCID4023707208-727-7S-allyl prop-2-ene-1-sulfinothioateDiallyldisulfid-S-oxid2-Propene-1-sulfinothioic acid, S-2-propenyl esterC6H10OS2S-Allyl acrylo-1-sulphinothioate

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

Experimental & physicochemical properties

Solubility24 mg/mL at 10 °C
Melting Point25 °C
Physical DescriptionSolid

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)

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Hazard Classes and CategoriesSkin Irrit. 2 (100%);Eye Irrit. 2 (100%);STOT SE 3 (100%)

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

Metabolism/MetabolitesDADSO is a known human metabolite of diallyl disulfide.
MeSH Pharmacological Classification · 5 items

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.

Cellular LocationsCytoplasm;Extracellular
Applications · 4 items

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

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017; +8613259417953 · [email protected]

Additional notes

DefinitionAn antibacterial substance extracted from garlic (allium).

Related reactions

5 records

Linked notes

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