3-(allylsulphinyl)-L-alanine Chemical Properties

Boiling point:

416.1±45.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

pka

1.88±0.10(Predicted)

color 

White to light yellow

BRN 

1724805

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

3-(allylsulphinyl)-L-alanine Usage And Synthesis

Description

Alliin is a cysteine sulfoxide constituent of garlic that is converted by alliinase to allicin, which imparts its pungent aroma and flavor. Alliin exhibits anti-cancer, anti-microbial, anti-hypertensive, cardioprotective, and anti-oxidant activities. It has been shown to inhibit squalene monooxygenase, a rate-limiting step in the downstream pathway of cholesterol biosynthesis, with an IC₅₀ value of 120 μM.

Uses

rac-Alliin has shown notable preventive effects on cardiac marker enzymes and lipids in isoproterenol-induced myocardial injury. rac-Alliin is also known to exhibit anticancer, antimicrobial, antihypertensive, antioxidant activities.

Uses

(±)-L-Alliin has been used in nutrient broth No. 2 (NB2) for determining the concentrations of garlic-derived products active against Clostridium jejuni.

Definition

ChEBI: 3-(Allylsulphinyl)-L-alanine is a L-alpha-amino acid.

General Description

Alliin is the precursor of allicin.

Biochem/physiol Actions

S-Allyl-L-cysteine ((±)-L-Alliin) (SAC) may be used to study its potential as an anti-Alzheimer′s factor. SAC has been shown to increase cell proliferation and neuroblast differentiation by increasing 5-HT(1A) and provide antioxidative benefit to neurons and synapses.

References

[1] TVRTKO KARLO KOVA?EVI?. The Interplay of Physiological and Biochemical Response to Short-Term Drought Exposure in Garlic (Allium sativum L.).[J]. Plants-Basel, 2023, 12 18. DOI: 10.3390/plants12183215
[2] CHIEKO OHSUMI  Konosuke S  Takahisa Hayashi. Formation of alliin in the culture tissues of Allium sativum. Oxidation of S-allyl-l-cysteine[J]. Phytochemistry, 1993, 33 1: Pages 107-111. DOI: 10.1016/0031-9422(93)85404-f
[3] S.M. ASDAQ  M. N I. Potential of garlic and its active constituent, S-allyl cysteine, as antihypertensive and cardioprotective in presence of captopril[J]. Phytomedicine, 2010, 17 13: Pages 1016-1026. DOI: 10.1016/j.phymed.2010.07.012
[4] JI-MYUNG KIM. Structure?Activity Relationship of Neuroprotective and Reactive Oxygen Species Scavenging Activities for Allium Organosulfur Compounds[J]. Journal of Agricultural and Food Chemistry, 2006, 54 18: 6547-6553. DOI: 10.1021/jf060412c
[5] XAVIER LIEBEN LOUIS. Garlic extracts prevent oxidative stress, hypertrophy and apoptosis in cardiomyocytes: a role for nitric oxide and hydrogen sulfide.[J]. BMC Complementary and Alternative Medicine, 2012, 12: 140. DOI: 10.1186/1472-6882-12-140
[6] RADU VASILE BAGIU  Monica B  Brigitha Vlaicu. Chemical composition and in vitro antifungal activity screening of the Allium ursinum L. (Liliaceae).[J]. International Journal of Molecular Sciences, 2012, 13 2: 1426-1436. DOI: 10.3390/ijms13021426

3-(allylsulphinyl)-L-alanine (17795-26-5)Related Product Information

• 3-(allylsulphinyl)-L-alanine
• 3-(ethylsulfinyl)propanoic acid
• S-Allyl-D-cysteine