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

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-S1001

  • Specification : 98%

  • CAS number : 556-27-4

  • Formula : C6H11NO3S

  • Molecular Weight : 177.22

  • PUBCHEM ID : 9576089

  • Volume : 20mg

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Catalogue Number

BF-S1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

177.22

Appearance

Colorless massive crystals

Botanical Source

bulb of Allium sativum

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C=CCS(=O)CC(C(=O)O)N

Synonyms

(+)-L-Alliin/(2R)-3-(Allylsulfinyl)-2-aminopropanoic acid/(+/-)-S-2-propenyl-L-cysteine sulfoxide/alliin/3-((S)-allylsulfinyl)-L-alanine/3-(Allylsulfinyl)-L-alanine/L-Alanine, 3-[(S)-(1S)-2-propen-1-ylsulfinyl]-/L-Alanine, 3-(2-propenylsulfinyl)-, (S)-/alliin zwitterion/3-(2-Propen-1-ylsulfinyl)-L-alanine/Alliin (25 mg)/3-(prop-2-en-1-ylsulfinyl)-L-alanine/S-Allyl-L-cysteine Sulfoxide/(S)-3-(Allylsulphiny/3-[(S)-Allylsulfinyl]-L-alanine/L-(+)-S-2-(propenyl)cysteine sulfoxide/L-Alanine, 3-[(S)-2-propenylsulfinyl]-/ALLIIN(P)/3-(2-Propenylsulfinyl)-L-alanine/L-Alanine, 3-(2-propen-1-ylsulfinyl)-/(2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid

IUPAC Name

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

Density

1.4±0.1 g/cm3

Solubility

Flash Point

205.5±28.7 °C

Boiling Point

416.1±45.0 °C at 760 mmHg

Melting Point

165ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2942000000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:556-27-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31091093

Abstract

Several families of 3,4-dimethylthiolane-based compounds spontaneously formed upon cutting of onion (Allium cepa) were studied. We report the isolation of the first known example of a naturally occurring dithiolactone, 5-hydroxy-3,4-dimethylthiolane-2-thione (cepadithiolactone A, C6H10OS2). Furthermore, on the basis of conceivable spectroscopic evidence (MS, NMR, IR), we could disprove the structure previously proposed for onionin A (C9H16O2S2), which is shown to be in fact (E)-3,4-dimethyl-5-(1-propenylsulfinyl)thiolane-2-ol. The identification of hitherto unknown methyl and propyl homologues of onionin A (dubbed onionins B and C, respectively) is also reported. Furthermore, the existence of the methyl and propyl homologues of cepathiolanes A (C9H16O2S3), trivially named cepathiolanes B and C, respectively, has been newly revealed. The organoleptic properties of these 3,4-dimethylthiolanes and their role in the formation of the pink discoloration of processed onion were also evaluated.

KEYWORDS

3,4-dimethylthiolane; ajothiolane; allithiolane; cepadithiolactone; cepathiolane; discoloration; dithiolactone; garlicnin; isoalliin; onion; onionin; pinking; zwiebelane isomer

Title

Isoalliin-Derived Thiolanes Formed in Homogenized Onion.

Author

Štefanova I1, Zapal J2, Moos M3, Kuzma M2, Kubec R1.

Publish date

2019 Sep 4

PMID

31038061

Abstract

BACKGROUND:
Lower human salivary aldehyde dehydrogenase (hsALDH) activity increases the risk of aldehyde mediated pathogenesis including oral cancer. Alliin, the bioactive compound of garlic, exhibits many beneficial health effects.

OBJECTIVE:
To study the effect of alliin on hsALDH activity.

METHODS:
Enzyme kinetics was performed to study the effect of alliin on the activity of hsALDH. Different biophysical techniques were employed for structural and binding studies. Docking analysis was done to predict the binding region and the type of binding forces.

RESULTS:
Alliin enhanced the dehydrogenase activity of the enzyme. It slightly reduced the Km and significantly enhanced the Vmax value. At 1 µM alliin concentration, the initial reaction rate increased by about two times. Further, it enhanced the hsALDH esterase activity. Biophysical studies indicated a strong complex formation between the enzyme and alliin (binding constant, Kb: 2.35 ± 0.14 x 103 M-1). It changes the secondary structure of hsALDH. Molecular docking study indicated that alliin interacts to the enzyme near the substrate binding region involving some active site residues that are evolutionary conserved. There was a slight increase in the nucleophilicity of active site cysteine in the presence of alliin. Ligand efficiency metrics values indicate that alliin is an efficient ligand for the enzyme.

CONCLUSION:
Alliin activates the catalytic activity of the enzyme. Hence, consumption of alliincontaining garlic preparations or alliin supplements and use of alliin in pure form may lower aldehyde related pathogenesis including oral carcinogenesis.

Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.

KEYWORDS

Human salivary aldehyde dehydrogenase; activity; aldehyde; alliin; binding; ligand efficiency; oral carcinogenesis.

Title

Enhancement in the Catalytic Activity of Human Salivary Aldehyde Dehydrogenase by Alliin from Garlic: Implications in Aldehyde Toxicity and Oral Health.

Author

Laskar AA1, Danishuddin2, Khan SH1, Subbarao N2, Younus H1.

Publish date

2019

PMID

30885435

Abstract

Alliin is an important organosulfur compound derived from garlic. In this study, the role of alliin in myocardial ischemia-reperfusion (I/R) injury and its underlying mechanisms were investigated. Treatment with alliin significantly reduced the area at risk and the infarct area in a mouse model of I/R injury. Besides, compared with I/R group, the cardiac function was significantly improved in I/R + alliin group. Treatment with alliin attenuated hypoxia/reoxygenation (H/R) induced apoptosis of cardiomyocytes. The results of the following high throughput RNA-sequencing revealed that autophagy participates in the myocardial protection role of alliin. Treatment with alliin decreased apoptosis and increased the autophagy activity in vivo. Autophagic flux in primary mouse cardiomyocytes was monitored using mRFP-GFP-LC3 adenovirus, and the results indicated that alliin could increase the autophagic flux. Moreover, the myocardial protective effect of alliin could be reversed by administration of autophagy inhibitor 3-MA. In conclusion, all the results indicated that alliin alleviates myocardial ischemia-reperfusion injury by promoting autophagy.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Alliin; Apoptosis; Autophagy; Myocardial ischemia-reperfusion injury

Title

Alliin alleviates myocardial ischemia-reperfusion injury by promoting autophagy.

Author

Zhao R1, Xie E1, Yang X2, Gong B3.

Publish date

2019 Apr 30


Description :

Alliin, an orally active sulfoxide compound derived from garlic, exhibits hypoglycemic, antioxidant and anti-inflammatory activities[1][2].