Gamma cyclodextrin | CAS#17465-86-0 | biochemical

MedKoo Cat#: 461339 | Name: Gamma cyclodextrin

Featured

Description:

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

Gamma cyclodextrin is a biochemical found in some foods.

Chemical Structure

Gamma cyclodextrin

CAS#17465-86-0

Theoretical Analysis

MedKoo Cat#: 461339

Name: Gamma cyclodextrin

CAS#: 17465-86-0

Chemical Formula: C48H80O40

Exact Mass: 1296.4226

Molecular Weight: 1297.13

Elemental Analysis: C, 44.45; H, 6.22; O, 49.34

Price and Availability

Size	Price	Availability	Quantity
25g	USD 250.00	2 Weeks
100g	USD 450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Cyclooctaamylose; gamma cyclodextrin; Cyclooctapentylose; .gamma.-Cyclodextrin; g-cyclodextrin; γ-Cyclodextrin

IUPAC/Chemical Name

A name could not be generated for this structure.

InChi Key

GDSRMADSINPKSL-HSEONFRVSA-N

InChi Code

InChI=1S/C48H80O40/c49-1-9-33-17(57)25(65)41(73-9)82-34-10(2-50)75-43(27(67)19(34)59)84-36-12(4-52)77-45(29(69)21(36)61)86-38-14(6-54)79-47(31(71)23(38)63)88-40-16(8-56)80-48(32(72)24(40)64)87-39-15(7-55)78-46(30(70)22(39)62)85-37-13(5-53)76-44(28(68)20(37)60)83-35-11(3-51)74-42(81-33)26(66)18(35)58/h9-72H,1-8H2/t9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-/m1/s1

SMILES Code

OC[C@H]1O[C@@H]2O[C@H]3[C@@H]([C@H]([C@@H](O[C@H]4[C@@H]([C@H]([C@@H](O[C@H]5[C@@H]([C@H]([C@@H](O[C@H]6[C@@H]([C@H]([C@@H](O[C@H]7[C@@H]([C@H]([C@@H](O[C@H]8[C@@H]([C@H]([C@@H](O[C@H]9[C@@H]([C@H]([C@@H](O[C@H]1[C@@H]([C@H]2O)O)O[C@@H]9CO)O)O)O[C@@H]8CO)O)O)O[C@@H]7CO)O)O)O[C@@H]6CO)O)O)O[C@@H]5CO)O)O)O[C@@H]4CO)O)O)O[C@@H]3CO)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

>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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

γ-Cyclodextrin is an endogenous metabolite.

In vitro activity:

The most remarkable result came from a third compound that showed no antiviral activity in cell assays when delivered free in solution, but its γ-cyclodextrin complex exhibited a 50% effective concentration of 5 μM. Thus, the antiviral activity of these compounds can be significantly improved, even completely rescued, using γ-cyclodextrin as carrier molecule. Reference: Int J Nanomedicine. 2015 Mar 19;10:2249-59. https://pubmed.ncbi.nlm.nih.gov/25834436/

In vivo activity:

The γCD-treated mice covered a significantly larger distance per night (CON 8.6 km, γCD 12.4 km) and were significantly longer active (CON 340 min, γCD 437 min). Moreover, γCD-treated mice significantly performed better at the inverted screen test indicated by an enhanced Kondziela score (CON 3.10, γCD 4.63). These data suggest that dietary γCD leads to an increased endurance. Reference: J Physiol Pharmacol. 2020 Jun;71(3). https://pubmed.ncbi.nlm.nih.gov/32991317/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	77.09

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,297.13 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. Claveria-Gimeno R, Vega S, Grazu V, de la Fuente JM, Lanas A, Velazquez-Campoy A, Abian O. Rescuing compound bioactivity in a secondary cell-based screening by using γ-cyclodextrin as a molecular carrier. Int J Nanomedicine. 2015 Mar 19;10:2249-59. doi: 10.2147/IJN.S79480. PMID: 25834436; PMCID: PMC4371900. 2. Kallab M, Schuetzenberger K, Hommer N, Schäfer BJ, Schmidl D, Bergmeister H, Zeitlinger M, Tan A, Jansook P, Loftsson T, Stefansson E, Garhöfer G. Bio-Distribution and Pharmacokinetics of Topically Administered γ-Cyclodextrin Based Eye Drops in Rabbits. Pharmaceuticals (Basel). 2021 May 18;14(5):480. doi: 10.3390/ph14050480. PMID: 34070168; PMCID: PMC8158513. 3. Wupper S, Fischer A, Luersen K, Ipharraguerre IR, Chikamoto K, Furune T, Ishida Y, Terao K, Rimbach G. Effects of dietary gamma-cyclodextrin on voluntary activity and muscle strength in mice. J Physiol Pharmacol. 2020 Jun;71(3). doi: 10.26402/jpp.2020.3.08. Epub 2020 Sep 26. PMID: 32991317.

In vitro protocol:

In vivo protocol:

1. Kallab M, Schuetzenberger K, Hommer N, Schäfer BJ, Schmidl D, Bergmeister H, Zeitlinger M, Tan A, Jansook P, Loftsson T, Stefansson E, Garhöfer G. Bio-Distribution and Pharmacokinetics of Topically Administered γ-Cyclodextrin Based Eye Drops in Rabbits. Pharmaceuticals (Basel). 2021 May 18;14(5):480. doi: 10.3390/ph14050480. PMID: 34070168; PMCID: PMC8158513. 2. Wupper S, Fischer A, Luersen K, Ipharraguerre IR, Chikamoto K, Furune T, Ishida Y, Terao K, Rimbach G. Effects of dietary gamma-cyclodextrin on voluntary activity and muscle strength in mice. J Physiol Pharmacol. 2020 Jun;71(3). doi: 10.26402/jpp.2020.3.08. Epub 2020 Sep 26. PMID: 32991317.

1: Cho Y, Gutierrez L, Bordonaro M, Russo D, Anzelmi F, Hooven JT, Cerra C, Lazarova DL. Effects of propolis and gamma-cyclodextrin on intestinal neoplasia in normal weight and obese mice. Cancer Med. 2016 Sep;5(9):2448-58. doi: 10.1002/cam4.787. Epub 2016 Jun 5. PubMed PMID: 27265242; PubMed Central PMCID: PMC4898980. 2: Goo BG, Hwang YJ, Park JK. Bacillus thuringiensis: a specific gamma-cyclodextrin producer strain. Carbohydr Res. 2014 Mar 11;386:12-7. doi: 10.1016/j.carres.2013.12.005. Epub 2013 Dec 11. PubMed PMID: 24456970. 3: Soica C, Danciu C, Savoiu-Balint G, Borcan F, Ambrus R, Zupko I, Bojin F, Coricovac D, Ciurlea S, Avram S, Dehelean CA, Olariu T, Matusz P. Betulinic acid in complex with a gamma-cyclodextrin derivative decreases proliferation and in vivo tumor development of non-metastatic and metastatic B164A5 cells. Int J Mol Sci. 2014 May 9;15(5):8235-55. doi: 10.3390/ijms15058235. PubMed PMID: 24821543; PubMed Central PMCID: PMC4057729. 4: Ikeda S, Uchida T, Ichikawa T, Watanabe T, Uekaji Y, Nakata D, Terao K, Yano T. Complexation of tocotrienol with gamma-cyclodextrin enhances intestinal absorption of tocotrienol in rats. Biosci Biotechnol Biochem. 2010;74(7):1452-7. Epub 2010 Jul 7. PubMed PMID: 20622447. 5: Wu D, Chen S, Wang N, Chen J, Wu J. Gamma-cyclodextrin production using cyclodextrin glycosyltransferase from Bacillus clarkii 7364. Appl Biochem Biotechnol. 2012 Aug;167(7):1954-62. doi: 10.1007/s12010-012-9741-5. Epub 2012 May 27. PubMed PMID: 22644644. 6: Ruiz HK, Serrano DR, Dea-Ayuela MA, Bilbao-Ramos PE, Bolás-Fernández F, Torrado JJ, Molero G. New amphotericin B-gamma cyclodextrin formulation for topical use with synergistic activity against diverse fungal species and Leishmania spp. Int J Pharm. 2014 Oct 1;473(1-2):148-57. doi: 10.1016/j.ijpharm.2014.07.004. Epub 2014 Jul 3. PubMed PMID: 24998510. 7: Donovan JD, Lee SY, Lee Y. R-Index Measure of Microencapsulated Tributyrin in Gamma-Cyclodextrin Influenced by Drying Method. J Food Sci. 2016 Sep;81(9):S2252-7. doi: 10.1111/1750-3841.13415. Epub 2016 Aug 16. PubMed PMID: 27527112. 8: Upreti M, Strassburger K, Chen YL, Wu S, Prakash I. Solubility enhancement of steviol glycosides and characterization of their inclusion complexes with gamma-cyclodextrin. Int J Mol Sci. 2011;12(11):7529-53. doi: 10.3390/ijms12117529. Epub 2011 Nov 3. PubMed PMID: 22174615; PubMed Central PMCID: PMC3233421. 9: Xie T, Yue Y, Song B, Chao Y, Qian S. [Increasing of product specificity of gamma-cyclodextrin by mutating the active domain of alpha-cyclodextrin glucanotransferase from Paenibacillus macerans sp. 602-1]. Sheng Wu Gong Cheng Xue Bao. 2013 Sep;29(9):1234-44. Chinese. PubMed PMID: 24409687. 10: Matilainen L, Maunu SL, Pajander J, Auriola S, Jääskeläinen I, Larsen KL, Järvinen T, Jarho P. The stability and dissolution properties of solid glucagon/gamma-cyclodextrin powder. Eur J Pharm Sci. 2009 Mar 2;36(4-5):412-20. doi: 10.1016/j.ejps.2008.11.006. Epub 2008 Nov 19. PubMed PMID: 19059479. 11: Muankaew C, Jansook P, Stefánsson E, Loftsson T. Effect of γ-cyclodextrin on solubilization and complexation of irbesartan: influence of pH and excipients. Int J Pharm. 2014 Oct 20;474(1-2):80-90. doi: 10.1016/j.ijpharm.2014.08.013. Epub 2014 Aug 13. PubMed PMID: 25128698. 12: Li Z, Wang M, Wang F, Gu Z, Du G, Wu J, Chen J. gamma-Cyclodextrin: a review on enzymatic production and applications. Appl Microbiol Biotechnol. 2007 Nov;77(2):245-55. Epub 2007 Sep 22. Review. PubMed PMID: 17891389. 13: Higashi K, Tozuka Y, Moribe K, Yamamoto K. Salicylic acid/gamma-cyclodextrin 2:1 and 4:1 complex formation by sealed-heating method. J Pharm Sci. 2010 Oct;99(10):4192-200. doi: 10.1002/jps.22133. PubMed PMID: 20737628. 14: Marshall JJ, Miwa I. Kinetic difference between hydrolyses of gamma-cyclodextrin by human salivary and pancreatic alpha-amylases. Biochim Biophys Acta. 1981 Sep 15;661(1):142-7. PubMed PMID: 6170334. 15: Créminon C, Djedaïni-Pilard F, Vienet R, Péan C, Grognet JM, Grassi J, Perly B, Pradelles P. A new specific enzyme immunoassay allowing an efficient pharmacokinetic evaluation of gamma-cyclodextrin after intravenous administration to rats. Pharm Res. 1999 Sep;16(9):1407-11. PubMed PMID: 10496657. 16: Zhao MX, Li Y, Wang CJ. [Synthesis and bioactivity of the folate receptor targeted gamma-cyclodextrin-folate inclusion-coated CdSe/ZnS quantum dots]. Yao Xue Xue Bao. 2013 Apr;48(4):566-72. Chinese. PubMed PMID: 23833947. 17: Géczy J, Bruhwyler J, Scuvée-Moreau J, Seutin V, Masset H, Van Heugen JC, Dresse A, Lejeune C, Decamp E, Szente L, Szejtli J, Liégeois JF. The inclusion of fluoxetine into gamma-cyclodextrin increases its bioavailability: behavioral, electrophysiological and pharmacokinetic studies. Psychopharmacology (Berl). 2000 Sep;151(4):328-34. PubMed PMID: 11026739. 18: Spears JK, Karr-Lilienthal LK, Fahey GC Jr. Influence of supplemental high molecular weight pullulan or gamma-cyclodextrin on ileal and total tract nutrient digestibility, fecal characteristics, and microbial populations in the dog. Arch Anim Nutr. 2005 Aug;59(4):257-70. PubMed PMID: 16320814. 19: Takeda A, Akimoto K, Kondo Y, Hamada F. Double stranded DNA discrimination by di-pyrene modified gamma-cyclodextrin. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3240-3. doi: 10.1016/j.bmcl.2010.04.066. Epub 2010 Apr 18. PubMed PMID: 20452210. 20: Serio N, Levine M. Efficient extraction and detection of aromatic toxicants from crude oil and tar balls using multiple cyclodextrin derivatives. Mar Pollut Bull. 2015 Jun 15;95(1):242-7. doi: 10.1016/j.marpolbul.2015.04.008. Epub 2015 May 5. PubMed PMID: 25956442.