12-Crown-4
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561223

CAS#: 294-93-9

Description: 12-Crown-4 disrupts Aβ40 fibrils. 12-Crown-4 can enter into the hydrophobic core region and form competitive, hydrophobic interactions with key hydrophobic residues.


Price and Availability

Size
Price

1g
USD 180
Size
Price

5g
USD 340
Size
Price

12-Crown-4, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561223
Name: 12-Crown-4
CAS#: 294-93-9
Chemical Formula: C8H16O4
Exact Mass: 176.1049
Molecular Weight: 176.21
Elemental Analysis: C, 54.53; H, 9.15; O, 36.32


Synonym: 12-Crown-4; 12Crown4; 12 Crown 4; 12-C-4; 12C4; 12 C 4; 12-Crown-4 ether

IUPAC/Chemical Name: 1,4,7,10-Tetraoxacyclododecane

InChi Key: XQQZRZQVBFHBHL-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2

SMILES Code: O1CCOCCOCCOCC1


Technical Data

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).

Harmonized System Code:
293490


References

1: Wang YM, Ju XJ, Liu Z, Xie R, Wang W, Wu JF, Zhang YQ, Chu LY. Competitive molecular-/ion-recognition responsive characteristics of poly(N-isopropylacrylamide-co-benzo-12-crown-4-acrylamide) copolymers with benzo-12-crown-4 as both guest and host units. Macromol Rapid Commun. 2014 Jul;35(14):1280-6. doi: 10.1002/marc.201400054. Epub 2014 Apr 9. Erratum in: Macromol Rapid Commun. 2014 Dec;35(24):2101. PubMed PMID: 24719381.

2: Tripathi G, Ramanathan G. Structures and conformation of a benzo-12-crown-4 containing dipeptide. Biopolymers. 2015 May;104(3):148-55. doi: 10.1002/bip.22614. PubMed PMID: 25645572.

3: Agrawal N, Skelton AA. 12-Crown-4 Ether Disrupts the Patient Brain-Derived Amyloid-β-Fibril Trimer: Insight from All-Atom Molecular Dynamics Simulations. ACS Chem Neurosci. 2016 Oct 19;7(10):1433-1441. Epub 2016 Aug 11. PubMed PMID: 27454141.

4: Reuter K, Buchner MR, Thiele G, von Hänisch C. Stable Alkali-Metal Complexes of Hybrid Disila-Crown Ethers. Inorg Chem. 2016 May 2;55(9):4441-7. doi: 10.1021/acs.inorgchem.6b00267. Epub 2016 Apr 15. PubMed PMID: 27082743.

5: Elvidge BR, Arndt S, Zeimentz PM, Spaniol TP, Okuda J. Cationic rare-earth metal trimethylsilylmethyl complexes supported by THF and 12-crown-4 ligands: synthesis and structural characterization. Inorg Chem. 2005 Sep 19;44(19):6777-88. PubMed PMID: 16156637.

6: Kaneko F, Kashihara N, Tsuchida T, Okuyama K. Complexation of syndiotactic polystyrene with 12-crown-4. Macromol Rapid Commun. 2010 Mar 16;31(6):554-7. doi: 10.1002/marc.200900719. Epub 2009 Dec 23. PubMed PMID: 21590941.

7: Esenpınar AA, Durmuş M, Bulut M. Chromenone 12-crown-4 substituted zinc phthalocyanine complexes: investigation of spectral, photophysical and photochemical properties. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Oct 15;81(1):690-7. doi: 10.1016/j.saa.2011.07.003. Epub 2011 Jul 7. PubMed PMID: 21795111.

8: Akutagawa T, Hasegawa T, Nakamura T, Takeda S, Inabe T, Sugiura K, Sakata Y, Underhill AE. M+(12-crown-4) supramolecular cations (M+ = Na+, K+, Rb+, and NH4+) within Ni(2-thioxo-1,3-dithiole-4,5-dithiolate)2 molecular conductor. Inorg Chem. 2000 Jun 12;39(12):2645-51. PubMed PMID: 11197021.

9: Akutagawa T, Motokizawa T, Matsuura K, Nishihara S, Noro S, Nakamura T. Structural phase transition of magnetic [Ni(dmit)2]- salts induced by supramolecular cation structures of (M+)([12]crown-4)2. J Phys Chem B. 2006 Mar 30;110(12):5897-904. PubMed PMID: 16553396.

10: Wilcox K, Pacey GE. Chromogenic benzo- and monoaza-12-crown-4, 13-crown-4 and 14-crown-4 lithium-selective crown ethers. Talanta. 1991 Nov;38(11):1315-24. PubMed PMID: 18965304.

11: Masiker MC, Mayne CL, Boone BJ, Orendt AM, Eyring EM. 7Li NMR chemical shift titration and theoretical DFT calculation studies: solvent and anion effects on second-order complexation of 12-crown-4 and 1-aza-12-crown-4 with lithium cation in several aprotic solvents. Magn Reson Chem. 2010 Feb;48(2):94-100. doi: 10.1002/mrc.2542. PubMed PMID: 19950215.

12: Gao K, Xu C, Cui Z, Liu C, Gao L, Li C, Wu D, Cai HL, Wu XS. The growth mechanism and ferroelectric domains of diisopropylammonium bromide films synthesized via 12-crown-4 addition at room temperature. Phys Chem Chem Phys. 2016 Mar 21;18(11):7626-31. doi: 10.1039/c6cp00568c. PubMed PMID: 26956668.

13: Chu IK, Siu SO, Lam CN, Chan JC, Rodriquez CF. Formation of molecular radical cations of aliphatic tripeptides from their complexes with CuII(12-crown-4). Rapid Commun Mass Spectrom. 2004;18(16):1798-802. PubMed PMID: 15329872.

14: Harrington JM, Jones SB, White PH, Hancock RD. Possible role of relativistic effects in the plasticity of the coordination geometry of cadmium(II). A voltammetric study of the stability of the complexes of cadmium(II) with 12-crown-4,15-crown-5 and 18-crown-6 in aqueous solution and the structures of [Cd(benzo-18-crown-6)(NCS)(2)] and [K(18-crown-6)][Cd(SCN)(3)]. Inorg Chem. 2004 Jul 12;43(14):4456-63. PubMed PMID: 15236559.

15: Inokuchi Y, Nakatsuma M, Kida M, Ebata T. Conformation of Alkali Metal Ion-Benzo-12-Crown-4 Complexes Investigated by UV Photodissociation and UV-UV Hole-Burning Spectroscopy. J Phys Chem A. 2016 Aug 18;120(32):6394-401. doi: 10.1021/acs.jpca.6b06626. Epub 2016 Aug 4. PubMed PMID: 27459367.

16: Habata Y, Yamada S, Osaka F. Crown bowl: metallocyclophane by self-assembly of 4'-pyridylmethyl-armed 12-crown-4 ethers with Ag+ ions. Inorg Chem. 2006 Feb 6;45(3):987-91. PubMed PMID: 16441104.

17: Alizadeh N. A comparison of complexation of Li+ ion with macrocyclic ligands 15-crown-5 and 12-crown-4 in binary nitromethane-acetonitrile mixtures by using lithium-7 NMR technique and ab initio calculation. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Jan;78(1):488-93. doi: 10.1016/j.saa.2010.11.014. Epub 2010 Nov 23. PubMed PMID: 21146449.

18: Yu HR, Hu JQ, Lu XH, Ju XJ, Liu Z, Xie R, Wang W, Chu LY. Insights into the effects of 2:1 "sandwich-type" crown-ether/metal-ion complexes in responsive host-guest systems. J Phys Chem B. 2015 Jan 29;119(4):1696-705. doi: 10.1021/jp5079423. Epub 2015 Jan 17. PubMed PMID: 25562507.

19: Pacey GE, Wu YP. Ion-pair extractions with 12-crown-4 and its analogues. Talanta. 1984 Mar;31(3):165-8. PubMed PMID: 18963560.

20: Danis JA, Lin MR, Scott BL, Eichhorn BW, Runde WH. Coordination trends in alkali metal crown ether uranyl halide complexes: the series [A(crown)]2[UO(2)X(4)] where A=Li, Na, K and X=Cl, Br. Inorg Chem. 2001 Jul 2;40(14):3389-94. PubMed PMID: 11421684.