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539-86-6

Basic Information
CAS No.: 539-86-6
Name: Allicin
Molecular Structure:
Molecular Structure of 539-86-6 (Allicin)
Formula: C6H10OS2
Molecular Weight: 162.273
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:
Risk Codes:
Safety:
Transport Information:
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;
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

127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With nitrogen(II) oxide; trifluoroacetic acid In water for 5h; Mechanism; Ambient temperature; other time; also in absence of CF3COOH;
106-95-6

allyl bromide

539-86-6

allicin

Conditions
ConditionsYield
With sodium hydrogensulfide; dihydrogen peroxide Yield given. Multistep reaction;
556-27-4

Alliin

539-86-6

allicin

Conditions
ConditionsYield
With immobilized alliinase
Immobilized alliinase column;
With alliinase In water at 25 - 35℃; for 0.5h; pH=6.5 - 8.5; Time; Enzymatic reaction; Inert atmosphere;
870-23-5

prop-2-ene-1-thiol

A

2179-57-9

diallyl disulphide

B

539-86-6

allicin

Conditions
ConditionsYield
With dihydrogen peroxide for 0.25h; Product distribution / selectivity;
1195577-61-7

(S)-allyl-L-cysteine sulfoxide

A

539-86-6

allicin

B

127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With alliinase In water at 25 - 35℃; for 0.5h; pH=6.5 - 8.5; Enzymatic reaction; Inert atmosphere;

A

539-86-6

allicin

B

127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; water; Allium sativum alliinase Enzymatic reaction;
539-86-6

allicin

401567-22-4

6-(trifluoromethyl)benzo[d]thiazole-2-thiol

2-(allyldisulfanyl)-6-(trifluoromethyl)benzo[d]thiazole

Conditions
ConditionsYield
In methanol at 20℃;97%
539-86-6

allicin

120-53-6

6-ethoxy-2-mercaptobenzothiazole

2-(allyldisulfanyl)-6-ethoxybenzo[d]thiazole

Conditions
ConditionsYield
In methanol at 20℃;95%
539-86-6

allicin

52-89-1

l-cysteine hydrochloride

2281-22-3

(R)-2-amino-3-(allyldithio)propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 0.33h;90%
With sodium hydrogencarbonate
With sodium hydrogencarbonate In water for 0.33h; pH=6;480 mg
2268-79-3

2-mercapto-6-methylbenzothiazole

539-86-6

allicin

2-(allyldisulfanyl)-6-methylbenzo[d]thiazole

Conditions
ConditionsYield
In methanol at 20℃;90%
539-86-6

allicin

149-30-4

2-Mercaptobenzothiazole

2-(allyldisulfanyl)benzothiazole

Conditions
ConditionsYield
In methanol at 20℃;90%
539-86-6

allicin

15639-75-5

6-mercaptopurine riboside

S-allylthio-6-mercaptopurine riboside

Conditions
ConditionsYield
In ethanol for 4h; pH=7.2; aq. phosphate buffer;85%
In ethanol; water at 4℃; for 4h; pH=7.2; Phosphate buffer;85%
Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water pH=8.0 - 8.4;80%
With sodium hydrogencarbonate In ethanol; water at 20℃; for 10h; pH=8 - 8.4;80%
In ethanol at 20℃; pH=6.5; aq. phosphate buffer;
539-86-6

allicin

184826-39-9

(3,5,6-Trimethyl-pyrazin-2-yl)-methanethiol

2-((allyldisulfanyl)methyl)-3,5,6-trimethylpyrazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water at 60℃; for 10h; pH=8 - 8.4;49%
539-86-6

allicin

51618-29-2

6-chloro-2-mercaptobenzothiazole

2-(allyldisulfanyl)-6-chlorobenzo[d]thiazole

Conditions
ConditionsYield
In methanol at 20℃;40%
539-86-6

allicin

22876-20-6

6-chloro-2-mercaptobenzoxazole

2-(allyldisulfanyl)-6-chlorobenzoxazole

Conditions
ConditionsYield
In methanol at 20℃;40%
539-86-6

allicin

49559-83-3

2-mercapto-5-metossi-benzossazolo

2-(allyldisulfanyl)-5-methoxybenzoxazole

Conditions
ConditionsYield
In methanol at 20℃;31%
539-86-6

allicin

100-53-8

phenylmethanethiol

1-allyl-2-benzyldisulfane

Conditions
ConditionsYield
In methanol at 20℃;30%
539-86-6

allicin

67-03-8

Thiamine hydrochloride

554-44-9

N-(2-allyldisulfanyl-4-hydroxy-1-methyl-but-1-en-t-yl)-N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-formamide

Conditions
ConditionsYield
With sodium hydroxide; ethanol; water bei pH 8;
2179-57-9

diallyl disulphide

539-86-6

allicin

A

2-(2',3'-dithia-5'-hexenyl)-3,4-dihydro-2H-thiopyran

B

3-(2',3'-dithia-5'-hexenyl)-3,4-dihydro-2H-thiopyran

Conditions
ConditionsYield
at 100℃; for 0.25h; Product distribution; Mechanism; copyrolysis;A 0.22 % Chromat.
B 0.26 % Chromat.
52-90-4

L-Cysteine

539-86-6

allicin

2281-22-3

(R)-2-amino-3-(allyldithio)propionic acid

Conditions
ConditionsYield
In water 1.) r.t., 40 min, 2.) 0 deg C, overnight; Yield given;
In water for 0.5h;5.7 mmol
In water at 23 - 25℃;
In water at 20℃; for 2h;
539-86-6

allicin

A

62488-53-3

3-vinyl-4H-<1,2>-dithiin

B

2179-57-9

diallyl disulphide

C

2050-87-5

diallyl trisulfide

D

80028-57-5

2‐ethenyl‐4H‐1,3‐dithiine

Conditions
ConditionsYield
In chloroform-d1 at 25℃; for 144h;A 0.008 g
B 0.03 g
C 0.01 g
D 0.015 g
539-86-6

allicin

A

62488-53-3

3-vinyl-4H-<1,2>-dithiin

B

2179-57-9

diallyl disulphide

C

2050-87-5

diallyl trisulfide

D

80028-57-5

2‐ethenyl‐4H‐1,3‐dithiine

E

92285-00-2

(Z)-ajoene

F

92284-99-6

(E)-ajoene

Conditions
ConditionsYield
at 37℃; for 48h; Product distribution; other temperatures, other times;
539-86-6

allicin

A

104228-61-7

4,5,9-trithiadodeca-1,11-diene 9-oxide

B

92284-99-6

(E)-ajoene

Conditions
ConditionsYield
With acetic acid at 25℃; for 120h;A 0.220 g
B 0.024 g
539-86-6

allicin

A

92285-00-2

(Z)-ajoene

B

92284-99-6

(E)-ajoene

Conditions
ConditionsYield
In water; acetone at 63 - 64℃; for 4h; Mechanism; Product distribution; Heating; in water-benzene, 37 deg C, 48 h;
In water; benzene at 37℃; for 48h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
In water; acetone for 4h; Heating; Yield given. Yields of byproduct given;
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    Allicin Basic information Product Name: Allicin Synonyms: 2-propene-1-sulfinothioicacid,s-2-propenylester;alliosan;ALLICIN;ALLICIN(SH);ARICINE(P);Dianyctrsnlgide;Allisatin;DIALLYLTHIOSULPHINATE CAS: 539-86-6 MF: C6H10OS2 MW: 162.27 EINE

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    539-86-6

    Allicin 539-86-6

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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 .