| Identification | Back Directory | [Name]
3-(allylsulphinyl)-L-alanine | [CAS]
17795-26-5 | [Synonyms]
ACSO
rac-Alliin
(+/-)-L-Alliin
Einecs 241-773-6
3-(allylsulphinyl)-L-alanine
(+/-)-L-ALLIIN, >=90% (HPLC)
Alliin (Mixture of DiastereoMers)
L-Alanine, 3-(2-propenylsulfinyl)-
L-Cysteine, S-2-propen-1-yl-, S-oxide
(2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid | [EINECS(EC#)]
241-773-6 | [Molecular Formula]
C6H11NO3S | [MDL Number]
MFCD00151977 | [MOL File]
17795-26-5.mol | [Molecular Weight]
177.22 |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m0/s1 | [InChIKey]
XUHLIQGRKRUKPH-ITZCMCNPSA-N | [SMILES]
N[C@@H](CS(=O)CC=C)C(O)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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. | [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 |
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