Ajoene | CAS#92285-01-3 | anticancer disulfide

MedKoo Cat#: 462141 | Name: Ajoene

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ajoene is a disulfide that has been found in A. sativum and has diverse biological activities, including antibacterial, anticancer, antiplatelet, and antioxidant properties. Note: this product is supplied as a solution in ethyl acetate.

Chemical Structure

Ajoene

CAS#92285-01-3

Theoretical Analysis

MedKoo Cat#: 462141

Name: Ajoene

CAS#: 92285-01-3

Chemical Formula: C9H14OS3

Exact Mass: 234.0207

Molecular Weight: 234.39

Elemental Analysis: C, 46.12; H, 6.02; O, 6.83; S, 41.03

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Ajoene; (E/Z)-Ajoene

IUPAC/Chemical Name

2-propen-1-yl [3-(2-propen-1-ylsulfinyl)-1-propen-1-yl] disulfide

InChi Key

IXELFRRANAOWSF-FNORWQNLSA-N

InChi Code

InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+

SMILES Code

O=S(C/C=C/SSCC=C)CC=C

Appearance

Solution in ethyl acetate

Purity

>95% (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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 234.39 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

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Rev Iberoam Micol. 2006 Jun;23(2):75-80. Spanish. doi: 10.1016/s1130-1406(06)70017-1. PMID: 16854181. 5: Kaschula CH, Hunter R, Parker MI. Garlic-derived anticancer agents: structure and biological activity of ajoene. Biofactors. 2010 Jan-Feb;36(1):78-85. doi: 10.1002/biof.76. PMID: 20108330. 6: Li H, Jeong JH, Kwon SW, Lee SK, Lee HJ, Ryu JH. Z-Ajoene Inhibits Growth of Colon Cancer by Promotion of CK1α Dependent β-Catenin Phosphorylation. Molecules. 2020 Feb 6;25(3):703. doi: 10.3390/molecules25030703. PMID: 32041324; PMCID: PMC7037095. 7: Kaschula CH, Hunter R, Hassan HT, Stellenboom N, Cotton J, Zhai XQ, Parker MI. Anti-proliferation activity of synthetic ajoene analogues on cancer cell- lines. Anticancer Agents Med Chem. 2011 Mar;11(3):260-6. doi: 10.2174/187152011795347450. PMID: 21269251. 8: Yamamoto Raynbird M, Khokhar SS, Neef D, Evans GJS, Wirth T. Synthesis of Ajoene Analogues by Novel Synthetic Strategies. Chemistry. 2021 Feb 10;27(9):3008-3012. doi: 10.1002/chem.202005023. Epub 2021 Jan 19. PMID: 33283953. 9: Lee H, Heo JW, Kim AR, Kweon M, Nam S, Lim JS, Sung MK, Kim SE, Ryu JH. Z-ajoene from Crushed Garlic Alleviates Cancer-Induced Skeletal Muscle Atrophy. Nutrients. 2019 Nov 10;11(11):2724. doi: 10.3390/nu11112724. PMID: 31717643; PMCID: PMC6893518. 10: Nakamoto M, Kunimura K, Suzuki JI, Kodera Y. Antimicrobial properties of hydrophobic compounds in garlic: Allicin, vinyldithiin, ajoene and diallyl polysulfides. Exp Ther Med. 2020 Feb;19(2):1550-1553. doi: 10.3892/etm.2019.8388. Epub 2019 Dec 27. PMID: 32010337; PMCID: PMC6966194. 11: Choi JA, Cho SN, Lim YJ, Lee J, Go D, Kim SH, Song CH. Enhancement of the antimycobacterial activity of macrophages by ajoene. Innate Immun. 2018 Jan;24(1):79-88. doi: 10.1177/1753425917747975. Epub 2017 Dec 14. PMID: 29239661; PMCID: PMC6830758. 12: Kaschula CH, Tuveri R, Ngarande E, Dzobo K, Barnett C, Kusza DA, Graham LM, Katz AA, Rafudeen MS, Parker MI, Hunter R, Schäfer G. The garlic compound ajoene covalently binds vimentin, disrupts the vimentin network and exerts anti- metastatic activity in cancer cells. BMC Cancer. 2019 Mar 20;19(1):248. doi: 10.1186/s12885-019-5388-8. PMID: 30894168; PMCID: PMC6425727. 13: Silva F, Khokhar SS, Williams DM, Saunders R, Evans GJS, Graz M, Wirth T. Short Total Synthesis of Ajoene. Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12290-12293. doi: 10.1002/anie.201808605. Epub 2018 Aug 19. PMID: 30079981; PMCID: PMC6221122. 14: Hitchcock JK, Mkwanazi N, Barnett C, Graham LM, Katz AA, Hunter R, Schäfer G, Kaschula CH. The Garlic Compound Z-Ajoene, S-Thiolates COX2 and STAT3 and Dampens the Inflammatory Response in RAW264.7 Macrophages. Mol Nutr Food Res. 2021 Feb;65(3):e2000854. doi: 10.1002/mnfr.202000854. Epub 2020 Dec 18. PMID: 33274836. 15: Zhu ML, Zheng Z, Lou EZ, Zhao KT, He SY, Chen JY. [Anti-gastric cancer effects of Z Ajoene and its molecular mechanisms]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2021 Sep;37(5):514-519. Chinese. doi: 10.12047/j.cjap.6122.2021.069. PMID: 34816664. 16: Dirsch VM, Antlsperger DS, Hentze H, Vollmar AM. Ajoene, an experimental anti-leukemic drug: mechanism of cell death. Leukemia. 2002 Jan;16(1):74-83. doi: 10.1038/sj.leu.2402337. PMID: 11840266. 17: Cho SJ, Ryu JH, Surh YJ. Ajoene, a Major Organosulfide Found in Crushed Garlic, Induces NAD(P)H:quinone Oxidoreductase Expression Through Nuclear Factor E2-related Factor-2 Activation in Human Breast Epithelial Cells. J Cancer Prev. 2019 Jun;24(2):112-122. doi: 10.15430/JCP.2019.24.2.112. Epub 2019 Jun 30. PMID: 31360690; PMCID: PMC6619855. 18: Kusza DA, Hunter R, Schäfer G, Smith M, Katz AA, Kaschula CH. Activity-Based Proteomic Identification of the S-Thiolation Targets of Ajoene in MDA- MB-231 Breast Cancer Cells. J Agric Food Chem. 2022 Nov 23;70(46):14679-14692. doi: 10.1021/acs.jafc.2c04972. Epub 2022 Nov 9. PMID: 36351177. 19: Jakobsen TH, van Gennip M, Phipps RK, Shanmugham MS, Christensen LD, Alhede M, Skindersoe ME, Rasmussen TB, Friedrich K, Uthe F, Jensen PØ, Moser C, Nielsen KF, Eberl L, Larsen TO, Tanner D, Høiby N, Bjarnsholt T, Givskov M. Ajoene, a sulfur-rich molecule from garlic, inhibits genes controlled by quorum sensing. Antimicrob Agents Chemother. 2012 May;56(5):2314-25. doi: 10.1128/AAC.05919-11. Epub 2012 Feb 6. PMID: 22314537; PMCID: PMC3346669. 20: Han CY, Ki SH, Kim YW, Noh K, Lee DY, Kang B, Ryu JH, Jeon R, Kim EH, Hwang SJ, Kim SG. Ajoene, a stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activation. Antioxid Redox Signal. 2011 Jan 15;14(2):187-202. doi: 10.1089/ars.2010.3190. Epub 2010 Sep 6. PMID: 20560786.