(+)-Alliin - 10mM in DMSO , CAS No.556-27-4

CAS: 556-27-4 Cat. No.: A424735 Molecular Weight: 177.22 EC Number: 209-118-9

GRADE & PURITY 10mM in DMSO

Synonyms

ACSO | Alliin | S-allyl-l-cysteine sulphoxide | 4-(5-formyl-2-furanyl)benzoic acid ethyl ester | Ethyl 4-hydroxy-6,8-dimethyl-3-quinolinecarboxylate | (+/-)-L-Alliin, >=90% (HPLC) | 4,4'-Ethylidenediphenol | (2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

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. S-allyl-cysteine is oxidized stereospecifically to (+)-alliin by garlic tissue cultures.
A orally acyclic nucleoside

Specifications

Synonyms

ACSO | Alliin | S-allyl-l-cysteine sulphoxide | 4-(5-formyl-2-furanyl)benzoic acid ethyl ester | Ethyl 4-hydroxy-6, 8-dimethyl-3-quinolinecarboxylate | (+/-)-L-Alliin, >=90% (HPLC) | 4, 4'-Ethylidenediphenol | (2R)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C=CCS(=O)CC(C(=O)O)N
• IUPAC Name: (2R)-2-amino-3-prop-2-enylsulfinylpropanoic acid
• InChIKey: XUHLIQGRKRUKPH-ITZCMCNPSA-N
• 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
• Isomeric SMILES: C=CCS(=O)C[C@@H](C(=O)O)N
• Molecular Weight: 177.22
• Reaxy-Rn: 3938807
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3938807&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Sulfoxides Amino acids Allyl sulfur compounds Sulfinyl compounds Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Sulfoxide - Amino acid - Allyl sulfur compound - Sulfinyl compound - Monocarboxylic acid or derivatives - Carboxylic acid - Carbonyl group - Amine - Hydrocarbon derivative - Organic nitrogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: non-proteinogenic alpha-amino acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Penicillium oxalicum (133 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Micrococcus luteus (7463 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aspergillus fumigatus (16427 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 177.220 g/mol
• XLogP3: -3.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 177.046 Da
• Monoisotopic Mass: 177.046 Da
• Topological Polar Surface Area: 99.600 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 181.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jing Nie, Rui Weng, Chunlin Li, Xiuhua Liu, Fang Wang, Karyne M. Rogers, Yongzhong Qian, Yongzhi Zhang, Yuwei Yuan.  (2022)  Chemometric origin classification of Chinese garlic using sulfur-containing compounds, assisted by stable isotopes and bioelements.  FOOD CHEMISTRY,      [PMID:35759834] [10.1016/j.foodchem.2022.133557]

2. Ruixuan Zhao, Hui Zou, Renjie Zhao, Ningyang Li, Zhenjia Zheng, Xuguang Qiao.  (2021)  Effect of amino acids on formation of pigment precursors in garlic discoloration using UPLC–ESI-Q-TOF-MS analysis.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2021.104231]

3. Wen-Qing Li, Hua Zhou, Mei-Yun Zhou, Xing-Peng Hu, Shi-Yi Ou, Ri-An Yan, Xiao-Jian Liao, Xue-Song Huang, Liang Fu.  (2015)  Characterization of Phenolic Constituents Inhibiting the Formation of Sulfur-Containing Volatiles Produced during Garlic Processing.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:25579175] [10.1021/jf505982f]

4. Shutian Ma, Enjie Diao, Hongyu Zou, Zhuang Shi, Yi Yang, Liming Zhang, Jinglin Zhang.  (2024)  Electron beam irradiation shortened the processing cycle of Chinese solo-bulb black garlic: Changes in critical physicochemical properties.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2024.106842]

5. Shutian Ma, Hongyu Zou, Manling Zhang, Jinyuan Zhang, Zhuang Shi, Yi Yang, Jinglin Zhang, Yuang Zhang, Liming Zhang, Enjie Diao.  (2026)  Effects of Processing Relative Humidity on Physicochemical Properties and Antioxidant Capacity of Black Garlic.  JOURNAL OF FOOD PROCESS ENGINEERING,  49  (2): (e70394).  [PMID:] [10.1111/jfpe.70394]