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539-86-6

Basic Information
CAS No.: 539-86-6
Name: Allicin
Article Data: 41
Cas Database
Molecular Structure:
Molecular Structure of 539-86-6 (Allicin)
Formula: C6H10OS2
Molecular Weight: 162.277
Synonyms: 2-Propene-1-sulfinothioicacid, S-2-propen-1-yl ester;2-Propene-1-sulfinicacid, thio-, S-allyl ester (7CI,8CI);2-Propene-1-sulfinothioic acid,S-2-propenyl ester (9CI);Alliosan;Diallylthiosulfinate;Thio-2-propene-1-sulfinic acid S-allyl ester;
EINECS: 208-727-7
Density: 1.148 g/cm3
Melting Point: 25°C
Boiling Point: 248.6 °C at 760 mmHg
Flash Point: 104.2 °C
Solubility: slightly soluble in ethanol, insoluble in water, glycerin and propylene glycol
Appearance: Clear to slightly yellow liquid
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 61.58000
LogP: 2.62100
Synthetic route
17795-27-6

S‐allyl‐L‐cysteine sulfoxide

539-86-6

allicin

Conditions
ConditionsYield
With water extract of garlic In water at 20℃; Enzymatic reaction;99%
2179-57-9

diallyl disulphide

539-86-6

allicin

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at -50 - -20℃; for 0.75h; Product distribution / selectivity; Inert atmosphere;96%
With Peroxyformic acid In methanol at 0℃; for 0.25h; Reagent/catalyst;92%
With peracetic acid; sodium carbonate In chloroform at 0℃; 1.) 30 min; 2.) 30 min;90%

C14H30OSSi

539-86-6

allicin

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 3h;71%

C13H28OSSi

539-86-6

allicin

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 3h; Reagent/catalyst; Solvent; Temperature;64%

C10H22OSSi

539-86-6

allicin

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 3h; Reagent/catalyst; Solvent; Temperature;29%
79-21-0

peracetic acid

2179-57-9

diallyl disulphide

67-66-3

chloroform

539-86-6

allicin

93-59-4

Perbenzoic acid

2179-57-9

diallyl disulphide

67-66-3

chloroform

539-86-6

allicin

Conditions
ConditionsYield
enzymatischer Abbau durch Alliinase; (+)(2R)-2-amino-3-allylsulfinyl-propionic acid;
durch Einwirkung von Alliinase;
alliinase rich garlic juice extract at 30℃; for 3h; Product distribution / selectivity; Enzymatic reaction;
With Petiveria alliacea L. alliinase; Petiveria alliacea lachrymatory factor synthase; pyridoxal 5'-phosphate; NAD at 20℃; for 0.333333h; pH=8; aq. phosphate buffer;
1072-43-1

propylene sulphide

539-86-6

allicin

Conditions
ConditionsYield
With sodium periodate
21593-77-1, 49621-03-6

S-allyl cysteine

A

2179-57-9

diallyl disulphide

B

539-86-6

allicin

C

29418-05-1

bis-2-propenyl thiosulfonate

D

113-24-6

sodium pyruvate

Conditions
ConditionsYield
With nitrogen(II) oxide In water for 24h; Ambient temperature; Yield given. Yields of byproduct given;
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Chemistry

Structure of Allicin (CAS NO.539-86-6):

IUPAC Name: 3-prop-2-enylsulfinylsulfanylprop-1-ene 
Empirical Formula: C6H10OS2
Molecular Weight: 162.273 
EINECS: 208-727-7 
Index of Refraction: 1.567
Molar Refractivity: 46.15 cm3
Molar Volume: 141.2 cm3
Polarizability: 18.29×10-24cm3
Surface Tension: 47.3 dyne/cm
Density: 1.148 g/cm3
Flash Point: 104.2 °C
Enthalpy of Vaporization: 46.61 kJ/mol
Boiling Point: 248.6 °C at 760 mmHg
Vapour Pressure: 0.0379 mmHg at 25°C 
Product Categories: plant extract 
Canonical SMILES: C=CCSS(=O)CC=C
InChI: InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
InChIKey: JDLKFOPOAOFWQN-UHFFFAOYSA-N

History

     Allicin is an organic compound obtained from garlic. It is also obtainable from onions, and other species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito in 1944.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 60mg/kg (60mg/kg)   Journal of the American Chemical Society. Vol. 66, Pg. 1950, 1944.
mouse LD50 subcutaneous 120mg/kg (120mg/kg)   Journal of the American Chemical Society. Vol. 66, Pg. 1950, 1944.

Specification

  Allicin , its cas register number is 64058-30-6. It also can be called 4-04-00-00007 (Beilstein Handbook Reference) ; Allylthiosulphinic acid allyl ester ; Diallyl thiosulfinate ; Diallyldisulfid-S-oxid ; Thio-2-propene-1-sulfinic acid S-allyl ester .