• Name

  (S)-3-(Allylsulphinyl)-L-alanine

• EINECS 209-118-9
• CAS No. 556-27-4
• Article Data20
• CAS DataBase
• Density 1.354 g/cm³
• Solubility
• Melting Point 165oC
• Formula C₆H₁₁NO₃S
• Boiling Point 416.1 °C at 760 mmHg
• Molecular Weight 177.224
• Flash Point 205.5 °C
• Transport Information
• Appearance White to off white crystalline powder
• Safety 26
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms Alanine,3-(allylsulfinyl)- (7CI);Alanine, 3-(allylsulfinyl)-, (S)-L- (8CI);L-Alanine,3-(2-propenylsulfinyl)-, (S)-;L-Alanine, 3-[(S)-2-propenylsulfinyl]- (9CI);(+)-L-Alliin;Alliin;S-Allyl-L-cysteine-(+)-sulfoxide;
• PSA 99.60000
• LogP 0.89900

Synthetic route

(Rc,Ss)-S-allyl-L-cysteine sulfoxide methyl ester

556-27-4

Alliin

Conditions

Conditions	Yield
With sodium methylate In methanol; water at -20℃; for 2h;	28.2%

21593-77-1, 49621-03-6

S-allyl cysteine

A

(2R)-2-amino-3-[(R)-prop-2-enylsulfinyl]propanoic acid

B

556-27-4

Alliin

Conditions

Conditions	Yield
With dihydrogen peroxide for 0.5h; Ambient temperature;
With dihydrogen peroxide for 0.75h; Ambient temperature;
With tris buffer pH 9.0; NADPH at 25℃; for 3h; cyclohexanone oxygenase (EC 1.14.13.22); Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With DL-dithiothreitol; iron(II) sulfate In aq. buffer at 28℃; for 16h; pH=6; Enzymatic reaction; diastereoselective reaction;	A n/a B n/a
With dihydrogen peroxide In water at 25℃; for 48h;

N-tert-butoxycarbonyl-S-(2-propenyl)-L-cysteine fluoren-9-ylmethyl ester S-oxide

A

(2R)-2-amino-3-[(R)-prop-2-enylsulfinyl]propanoic acid

B

556-27-4

Alliin

Conditions

Conditions	Yield
With diethylamine; trifluoroacetic acid 1) r.t., 2 h, 2) CH2Cl2, r.t., 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

328975-04-8

(2R)-3-allylsulfanyl-2-amino-propionic acid methyl ester

556-27-4

Alliin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide / water; acetonitrile / 26 h / 20 °C 2: sodium methylate / methanol; water / 2 h / -20 °C View Scheme

24424-99-5

di-tert-butyl dicarbonate

556-27-4

Alliin

C11H19NO5S

Conditions

Conditions	Yield
With triethylamine In water; acetone at 10 - 45℃; under 1520.1 Torr; for 5h;	94%

556-27-4

Alliin

A

539-86-6

allicin

B

29418-05-1

bis-2-propenyl thiosulfonate

C

127-17-3

2-oxo-propionic acid

Conditions

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

...Expand

556-27-4

Alliin

539-86-6

allicin

Conditions

Conditions	Yield
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;

75-66-1

2-methylpropan-2-thiol

556-27-4

Alliin

643-79-8

o-phthalic dicarboxaldehyde

C18H23NO3S2

Conditions

Conditions	Yield
In methanol at 20℃; for 0.5h; Darkness; aq. buffer;

...Expand

52-90-4

L-Cysteine

556-27-4

Alliin

21593-77-1, 49621-03-6

S-allyl cysteine

Conditions

Conditions	Yield
In water at 80℃; for 24h; Sealed tube;	2.1 mg

556-27-4

Alliin

C23H35N3O6S

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C View Scheme

556-27-4

Alliin

tapentadol-3-(N-methyl-N-((S)-3-(allylsulfinyl)-L-alanyl(methyl)amino))ethyl carbamate

Conditions

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 7 h / 20 °C View Scheme

556-27-4

Alliin

C15H29N3O4S

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C View Scheme

556-27-4

Alliin

C30H50N4O6S

Conditions

Conditions

Yield

Multi-step reaction with 4 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C View Scheme

556-27-4

Alliin

C25H42N4O4S*ClH

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / acetone; water / 5 h / 10 - 45 °C / 1520.1 Torr 2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 0.25 h 2.3: 3 h / 20 °C 3.1: rosenmund catalyst; hydrogen / methanol / 40 - 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 7 h / 20 °C 6.1: hydrogenchloride / water; methanol / 1 h / 40 - 45 °C / pH 1 - 2 View Scheme

(S)-3-(Allylsulphinyl)-L-alanine Chemical Properties

(S)-3-(Allylsulphinyl)-L-alanine Safety Profile

(S)-3-(Allylsulphinyl)-L-alanine Specification