WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H540006
CAS#: 556-27-4
Description: Alliin is an optically active synthetic cysteine derivative, NMDA receptor agonist and antioxidant. It also inhibits VEGF-induced angiogenesis in fibrosarcoma cells.
Hodoodo Cat#: H540006
Name: Alliin
CAS#: 556-27-4
Chemical Formula: C6H11NO3S
Exact Mass: 177.05
Molecular Weight: 177.218
Elemental Analysis: C, 40.67; H, 6.26; N, 7.90; O, 27.08; S, 18.09
Synonym: EINECS 209-118-9; S-Allyl-L-cysteine-S-oxide; Alliin
IUPAC/Chemical Name: ((S)-allylsulfinyl)-D-alanine
InChi Key: XUHLIQGRKRUKPH-DYEAUMGKSA-N
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
SMILES Code: N[C@@H](C[S@](CC=C)=O)C(O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | The cysteine sulfoxide constituent of garlic. |
| In vitro activity: | 3T3-L1 cells showed fibroblastic-like morphology before adipogenic induction (Fig. 1A-a and -b). Then, the suppression effect of alliin on adipogenic differentiation was examined. During adipogenic differentiation, the 3T3-L1 cells were treated with different concentrations of alliin (10, 20, 40 µg/ml) for 7 days, and the cells treated without alliin were used as control. 3T3-L1 cells showed a morphological change from fibroblastic-shape to round-shape, and then oil droplets were formed and maintained after 7 days of induction (Fig. 1A-c-f). The Oil red O-stained area decreased significantly in the alliin-treated groups compared with the control group (Fig. 1A-g-j). Meanwhile, quantitative analysis showed that alliin-treated group displayed dramatically lower lipid accumulation in a dose-dependent manner compared to the control group. 40 µg/ml alliin treatment showed the greatest effects on the lipid accumulation which level dropped to 39.5% (Fig. 1B). The effect of alliin on cell viability was examined. 3T3-L1 cells were treated with different concentrations of alliin (10-40 µg/ml) for 7 days. Alliin has no effect on cell viability even at a concentration of 40 µg/ml (Fig. 1C). These data indicated that alliin may contain anti-adipogenic potential. Reference: Exp Ther Med. 2021 Jun; 21(6): 563. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8027764/ |
| In vivo activity: | The weight of the adipose deposit of the epididymis was differently affected in relation to the type of diet administered, but alliin treatment did not show an effect in any of the groups (Table 2). This notwithstanding, at the cellular level, the high-fat diet increased the size of the adipocytes of the HFD group compared to the STD group (p < 0.0001). When alliin was administered in the HFD+A group, the size of the adipocytes decreased significantly (HFD+A vs. HFD p < 0.0001), although the HFD+A group still presented a greater size than the control groups (both STD or STD+A; p < 0.0001) (Figure 4). Reference: Nutrients. 2020 Mar; 12(3): 624. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146142/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 3.0 | 16.93 | |
| PBS (pH 7.2) | 10.0 | 56.43 |
The following data is based on the product molecular weight 177.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Li N, Chen K, Dong H, Yang J, Yoshizawa M, Kagami H, Li X. Alliin inhibits adipocyte differentiation by downregulating Akt expression: Implications for metabolic disease. Exp Ther Med. 2021 Jun;21(6):563. doi: 10.3892/etm.2021.9995. Epub 2021 Mar 26. PMID: 33850535; PMCID: PMC8027764. 2. Cheng B, Li T. Discovery of alliin as a putative inhibitor of the main protease of SARS-CoV-2 by molecular docking. Biotechniques. 2020 Aug;69(2):108-112. doi: 10.2144/btn-2020-0038. Epub 2020 May 27. PMID: 32459144; PMCID: PMC7273901. 3. Sánchez-Sánchez MA, Zepeda-Morales ASM, Carrera-Quintanar L, Viveros-Paredes JM, Franco-Arroyo NN, Godínez-Rubí M, Ortuño-Sahagun D, López-Roa RI. Alliin, an Allium sativum Nutraceutical, Reduces Metaflammation Markers in DIO Mice. Nutrients. 2020 Feb 27;12(3):624. doi: 10.3390/nu12030624. PMID: 32120804; PMCID: PMC7146142. 4. Yue LJ, Zhu XY, Li RS, Chang HJ, Gong B, Tian CC, Liu C, Xue YX, Zhou Q, Xu TS, Wang DJ. S‑allyl‑cysteine sulfoxide (alliin) alleviates myocardial infarction by modulating cardiomyocyte necroptosis and autophagy. Int J Mol Med. 2019 Nov;44(5):1943-1951. doi: 10.3892/ijmm.2019.4351. Epub 2019 Sep 26. PMID: 31573046; PMCID: PMC6777694. |
| In vitro protocol: | 1. Li N, Chen K, Dong H, Yang J, Yoshizawa M, Kagami H, Li X. Alliin inhibits adipocyte differentiation by downregulating Akt expression: Implications for metabolic disease. Exp Ther Med. 2021 Jun;21(6):563. doi: 10.3892/etm.2021.9995. Epub 2021 Mar 26. PMID: 33850535; PMCID: PMC8027764. 2. Cheng B, Li T. Discovery of alliin as a putative inhibitor of the main protease of SARS-CoV-2 by molecular docking. Biotechniques. 2020 Aug;69(2):108-112. doi: 10.2144/btn-2020-0038. Epub 2020 May 27. PMID: 32459144; PMCID: PMC7273901. |
| In vivo protocol: | 1. Sánchez-Sánchez MA, Zepeda-Morales ASM, Carrera-Quintanar L, Viveros-Paredes JM, Franco-Arroyo NN, Godínez-Rubí M, Ortuño-Sahagun D, López-Roa RI. Alliin, an Allium sativum Nutraceutical, Reduces Metaflammation Markers in DIO Mice. Nutrients. 2020 Feb 27;12(3):624. doi: 10.3390/nu12030624. PMID: 32120804; PMCID: PMC7146142. 2. Yue LJ, Zhu XY, Li RS, Chang HJ, Gong B, Tian CC, Liu C, Xue YX, Zhou Q, Xu TS, Wang DJ. S‑allyl‑cysteine sulfoxide (alliin) alleviates myocardial infarction by modulating cardiomyocyte necroptosis and autophagy. Int J Mol Med. 2019 Nov;44(5):1943-1951. doi: 10.3892/ijmm.2019.4351. Epub 2019 Sep 26. PMID: 31573046; PMCID: PMC6777694. |
1: Chen Z, Xu M, Wang C, Zhou H, Fan L, Huang X. Thermolysis kinetics and thermal degradation compounds of alliin. Food Chem. 2017 May 15;223:25-30. doi: 10.1016/j.foodchem.2016.12.011. Epub 2016 Dec 9. PubMed PMID: 28069119.
2: Yoshimoto N, Onuma M, Mizuno S, Sugino Y, Nakabayashi R, Imai S, Tsuneyoshi T, Sumi S, Saito K. Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic. Plant J. 2015 Sep;83(6):941-51. doi: 10.1111/tpj.12954. PubMed PMID: 26345717.
3: Hakamata W, Koyama R, Tanida M, Haga T, Hirano T, Akao M, Kumagai H, Nishio T. A Simple Synthesis of Alliin and allo-Alliin: X-ray Diffraction Analysis and Determination of Their Absolute Configurations. J Agric Food Chem. 2015 Dec 23;63(50):10778-84. doi: 10.1021/acs.jafc.5b05501. Epub 2015 Dec 15. PubMed PMID: 26638713.
4: Shi L, Lin Q, Li X, Nie Y, Sun S, Deng X, Wang L, Lu J, Tang Y, Luo F. Alliin, a garlic organosulfur compound, ameliorates gut inflammation through MAPK-NF-κB/AP-1/STAT-1 inactivation and PPAR-γ activation. Mol Nutr Food Res. 2017 Mar 30. doi: 10.1002/mnfr.201601013. [Epub ahead of print] PubMed PMID: 28371322.
5: Jiang XM, Lu YM, Tan CP, -Liang Y, Cui B. Combination of aqueous two-phase extraction and cation-exchange chromatography: new strategies for separation and purification of alliin from garlic powder. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Apr 15;957:60-7. doi: 10.1016/j.jchromb.2014.02.037. Epub 2014 Mar 2. PubMed PMID: 24657412.
6: Morozova EA, Revtovich SV, Anufrieva NV, Kulikova VV, Nikulin AD, Demidkina TV. Alliin is a suicide substrate of Citrobacter freundii methionine γ-lyase: structural bases of inactivation of the enzyme. Acta Crystallogr D Biol Crystallogr. 2014 Nov;70(Pt 11):3034-42. doi: 10.1107/S1399004714020938. Epub 2014 Oct 29. PubMed PMID: 25372692.
7: Geng J, Zhang ZC, Zhang HB, Li XX, Chen J. [Determination of intrinsic alliin dissolution rates with fiber-optic sensing process analysis]. Yao Xue Xue Bao. 2014 Oct;49(10):1475-8. Chinese. PubMed PMID: 25577881.
8: Chen Y, Sun J, Dou C, Li N, Kang F, Wang Y, Cao Z, Yang X, Dong S. Alliin Attenuated RANKL-Induced Osteoclastogenesis by Scavenging Reactive Oxygen Species through Inhibiting Nox1. Int J Mol Sci. 2016 Sep 20;17(9). pii: E1516. PubMed PMID: 27657047; PubMed Central PMCID: PMC5037793.
9: Nasim SA, Dhir B, Kapoor R, Fatima S, Mahmooduzzafar, Mujib A. Alliin obtained from leaf extract of garlic grown under in situ conditions possess higher therapeutic potency as analyzed in alloxan-induced diabetic rats. Pharm Biol. 2011 Apr;49(4):416-21. doi: 10.3109/13880209.2010.521163. Epub 2011 Mar 11. PubMed PMID: 21391887.
10: Izdebska M, Grzanka D, Gagat M, Hałas-Wiśniewska M, Grzanka A. Downregulation of importin-9 protects MCF-7 cells against apoptosis induced by the combination of garlic-derived alliin and paclitaxel. Oncol Rep. 2016 May;35(5):3084-93. doi: 10.3892/or.2016.4628. Epub 2016 Feb 22. PubMed PMID: 26934847.
11: Quintero-Fabián S, Ortuño-Sahagún D, Vázquez-Carrera M, López-Roa RI. Alliin, a garlic (Allium sativum) compound, prevents LPS-induced inflammation in 3T3-L1 adipocytes. Mediators Inflamm. 2013;2013:381815. doi: 10.1155/2013/381815. Epub 2013 Dec 26. PubMed PMID: 24453416; PubMed Central PMCID: PMC3888727.
12: Tao D, Zhou B, Zhang L, Hu X, Liao X, Zhang Y. 'Laba' garlic processed by dense phase carbon dioxide: the relation between green colour generation and cellular structure, alliin consumption and alliinase activity. J Sci Food Agric. 2016 Jul;96(9):2969-75. doi: 10.1002/jsfa.7463. Epub 2015 Oct 21. PubMed PMID: 26374695.
13: Yoshimoto N, Yabe A, Sugino Y, Murakami S, Sai-Ngam N, Sumi S, Tsuneyoshi T, Saito K. Garlic γ-glutamyl transpeptidases that catalyze deglutamylation of biosynthetic intermediate of alliin. Front Plant Sci. 2015 Jan 8;5:758. doi: 10.3389/fpls.2014.00758. eCollection 2014. PubMed PMID: 25620969; PubMed Central PMCID: PMC4288057.
14: Wu T, Chen N, Liu C, Liu R, Zhang J, Xie X, Zhang M. Investigating the chemical constituent and the suppressive effects of alliin hydrolysate on E.coli. Nat Prod Res. 2017 Mar 2:0-4. doi: 10.1080/14786419.2017.1297440. [Epub ahead of print] PubMed PMID: 28278629.
15: Appel E, Vallon-Eberhard A, Rabinkov A, Brenner O, Shin I, Sasson K, Shadkchan Y, Osherov N, Jung S, Mirelman D. Therapy of murine pulmonary aspergillosis with antibody-alliinase conjugates and alliin. Antimicrob Agents Chemother. 2010 Feb;54(2):898-906. doi: 10.1128/AAC.01267-09. Epub 2009 Nov 30. PubMed PMID: 19949059; PubMed Central PMCID: PMC2812126.
16: Nasim SA, Dhir B, Samar F, Rashmi K, Mahmooduzzafa, Mujib A. Sulphur treatment alters the therapeutic potency of alliin obtained from garlic leaf extract. Food Chem Toxicol. 2009 Apr;47(4):888-92. PubMed PMID: 19271323.
17: Dethier B, Laloux M, Hanon E, Nott K, Heuskin S, Wathelet JP. Analysis of the diastereoisomers of alliin by HPLC. Talanta. 2012 Nov 15;101:447-52. doi: 10.1016/j.talanta.2012.09.058. Epub 2012 Oct 5. PubMed PMID: 23158347.
18: Chung LY. The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide. J Med Food. 2006 Summer;9(2):205-13. PubMed PMID: 16822206.
19: Yuan YZ, Gu J, Hang TJ, Chen J, Zhang ZX. [Related substances in purified alliin determined by HPLC-MS/MS]. Yao Xue Xue Bao. 2007 Jun;42(6):639-42. Chinese. PubMed PMID: 17702402.
20: Yuan Y, Hang T, Ji Y, Zhang Z. [Determination of alliin and its related substances in garlic using pre-column derivatization and reversed-phase high performance liquid chromatography]. Se Pu. 2008 Mar;26(2):242-5. Chinese. PubMed PMID: 18581860.
