The cysteine sulfoxide constituent of garlic
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Isomer(s)
14002(+)-Alliin
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(±)-Alliin

Item No. 14001

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-2-propen-1-yl-L-cysteine, S-oxide
CAS Number
17795-26-5
Synonyms
  • (±)-Allyl-L-cysteine sulfoxide
Molecular Formula
C6H11NO3S
Formula Weight
177.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
C=CCS(C[C@H](N)C(O)=O)=O
InChi Code
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
InChi Key
XUHLIQGRKRUKPH-ITZCMCNPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $94

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    10 mg

    $179

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    50 mg

    $742

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    Cayman Chemical
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    Product Description

    Alliin is a cysteine sulfoxide constituent of garlic that is converted by alliinase to allicin, which imparts its pungent aroma and flavor.1,2 Alliin exhibits anti-cancer, anti-microbial, anti-hypertensive, cardioprotective, and anti-oxidant activities.3,4,5 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.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jones, M.G., Collin, H.A., Tregova, A., et al. The biochemical and physiological genesis of alliin in garlic. Intl. J. Biomed. Pharma. Sci. 1(1), 21-24 (2007).

    2. Ohsumi, C., Hayashi, T., and Sano, K. Formation of alliin in the culture tissues of Allium sativum. Oxidation of S-allyl-L-cysteine. Phytochemistry 33(1), 107-111 (1993).

    3. Asdaq, S.M., and Inamdar, M.N. Potential of garlic and its active constituent, S-allyl cysteine, as antihypertensive and cardioprotective in presence of captopril. Phytomedicine 17(13), 1016-1026 (2010).

    4. Kim, J.M., Chang, H.J., Kim, W.K., et al. Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds. J. Agric. Food Chem. 54, 6547-6553 (2006).

    5. Louis, X.L., Murphy, R., Thandapilly, S.J., et al. Garlic extracts prevent oxidative stress, hypertrophy and apoptosis in cardiomyocytes: A role for nitric oxide and hydrogen sulfide. BMC Complement. Altern. Med. 12, 140 (2012).

    6. Bagiu, R.V., Vlaicu, B., and Butnariu, M. Chemical composition and in vitro antifungal activity screening of the Allium ursinum L. (Liliaceae). Int. J. Mol. Sci. 13, 1426-1436 (2012).

    7. Gupta, N., and Porter, T.D. Garlic and garlic-derived compounds inhibit human squalene monooxygenase. J. Nutr. 131(6), 1662-1667 (2001).