Homonojirimycin | CAS#119557-99-2 | alpha-glucosidase inhibitor

MedKoo Cat#: 592674 | Name: Homonojirimycin

Description:

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

Homonojirimycin inhibits alpha-glucosidase.

Chemical Structure

Homonojirimycin

CAS#119557-99-2

Theoretical Analysis

MedKoo Cat#: 592674

Name: Homonojirimycin

CAS#: 119557-99-2

Chemical Formula: C7H15NO5

Exact Mass: 193.0950

Molecular Weight: 193.20

Elemental Analysis: C, 43.52; H, 7.83; N, 7.25; O, 41.41

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Homonojirimycin

IUPAC/Chemical Name

(2R,3S,4R,5R,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

InChi Key

CLVUFWXGNIFGNC-OVHBTUCOSA-N

InChi Code

InChI=1S/C7H15NO5/c9-1-3-5(11)7(13)6(12)4(2-10)8-3/h3-13H,1-2H2/t3-,4-,5-,6+,7+/m1/s1

SMILES Code

OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](CO)N1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 193.20 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

1: Zhang G, Zhang B, Zhang X, Bing F. Homonojirimycin, an alkaloid from dayflower inhibits the growth of influenza A virus in vitro. Acta Virol. 2013;57(1):85-6. PubMed PMID: 23530829. 2: Zhang GB, Tian LQ, Li YM, Liao YF, Li J, Bing FH. Protective effect of homonojirimycin from Commelina communis (dayflower) on influenza virus infection in mice. Phytomedicine. 2013 Aug 15;20(11):964-8. doi: 10.1016/j.phymed.2013.04.009. Epub 2013 Jun 6. PubMed PMID: 23746956. 3: Glawar AF, Jenkinson SF, Newberry SJ, Thompson AL, Nakagawa S, Yoshihara A, Akimitsu K, Izumori K, Butters TD, Kato A, Fleet GW. An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic & thermodynamic azido-γ-lactones. Org Biomol Chem. 2013 Sep 25;11(40):6886-99. doi: 10.1039/c3ob41334a. PubMed PMID: 23963282. 4: Lenagh-Snow GM, Jenkinson SF, Newberry SJ, Kato A, Nakagawa S, Adachi I, Wormald MR, Yoshihara A, Morimoto K, Akimitsu K, Izumori K, Fleet GW. Eight stereoisomers of homonojirimycin from D-mannose. Org Lett. 2012 Apr 20;14(8):2050-3. doi: 10.1021/ol3005744. Epub 2012 Apr 3. PubMed PMID: 22472134. 5: Martin OR, Compain P, Kizu H, Asano N. Revised structure of a homonojirimycin isomer from Aglaonema treubii: first example of a naturally occurring alpha-homoallonojirimycin. Bioorg Med Chem Lett. 1999 Nov 1;9(21):3171-4. PubMed PMID: 10560746. 6: Asano N, Nishida M, Kato A, Kizu H, Matsui K, Shimada Y, Itoh T, Baba M, Watson AA, Nash RJ, Lilley PM, Watkin DJ, Fleet GW. Homonojirimycin isomers and N-alkylated homonojirimycins: structural and conformational basis of inhibition of glycosidases. J Med Chem. 1998 Jul 2;41(14):2565-71. PubMed PMID: 9651160. 7: Ikeda K, Takahashi M, Nishida M, Miyauchi M, Kizu H, Kameda Y, Arisawa M, Watson AA, Nash RJ, Fleet GW, Asano N. Homonojirimycin analogues and their glucosides from Lobelia sessilifolia and Adenophora spp. (Campanulaceae). Carbohydr Res. 2000 Jan 12;323(1-4):73-80. PubMed PMID: 10782288. 8: Markad SD, Karanjule NS, Sharma T, Sabharwal SG, Dhavale DD. Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-D-gluco-homonojirimycin and N-butyl 1-deoxy-L-ido-homonojirimycin. Bioorg Med Chem. 2006 Aug 15;14(16):5535-9. Epub 2006 May 8. PubMed PMID: 16682208. 9: Zeng Y, Pan YT, Asano N, Nash RJ, Elbein AD. Homonojirimycin and N-methyl-homonojirimycin inhibit N-linked oligosaccharide processing. Glycobiology. 1997 Mar;7(2):297-304. PubMed PMID: 9134436. 10: Saavedra OM, Martin OR. Chemical Synthesis of beta-Homonojirimycin, of Its N-Butyl Derivative, and of "Methyl Homoazacellobioside" . J Org Chem. 1996 Oct 4;61(20):6987-6993. PubMed PMID: 11667597. 11: Rodríguez-Sánchez S, Martín-Ortiz A, Carrero-Carralero C, Ramos S, Sanz ML, Soria AC. Pressurized liquid extraction of Aglaonema sp. iminosugars: Chemical composition, bioactivity, cell viability and thermal stability. Food Chem. 2016 Aug 1;204:62-9. doi: 10.1016/j.foodchem.2016.02.091. Epub 2016 Feb 15. PubMed PMID: 26988476. 12: Markad SD, Karanjule NS, Sharma T, Sabharwal SG, Dhavale DD. Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: Synthesis and glycosidase inhibition study. Org Biomol Chem. 2006 Oct 7;4(19):3675-80. Epub 2006 Aug 22. PubMed PMID: 16990944. 13: Asano N, Ishii S, Kizu H, Ikeda K, Yasuda K, Kato A, Martin OR, Fan JQ. In vitro inhibition and intracellular enhancement of lysosomal alpha-galactosidase A activity in Fabry lymphoblasts by 1-deoxygalactonojirimycin and its derivatives. Eur J Biochem. 2000 Jul;267(13):4179-86. PubMed PMID: 10866822. 14: Asano N, Kato A, Miyauchi M, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GW. Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. J Nat Prod. 1998 May;61(5):625-8. PubMed PMID: 9599261. 15: Patil NT, Tilekar JN, Dhavale DD. Intermolecular Michael addition of substituted amines to a sugar-derived alpha,beta-unsaturated ester: synthesis of 1-deoxy-D-gluco- and -L-ido-homonojirimycin, 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine. J Org Chem. 2001 Feb 23;66(4):1065-74. PubMed PMID: 11312931. 16: Kim HS, Kim YH, Hong YS, Paek NS, Lee HS, Kim TH, Kim KW, Lee JJ. alpha-Glucosidase inhibitors from Commelina communis. Planta Med. 1999 Jun;65(5):437-9. PubMed PMID: 10418330. 17: Lumbroso A, Beaudet I, Toupet L, Le Grognec E, Quintard JP. Stereodivergent synthesis of iminosugars from stannylated derivatives of (S)-vinylglycinol. Org Lett. 2013 Jan 4;15(1):160-3. doi: 10.1021/ol303213r. Epub 2012 Dec 20. PubMed PMID: 23256678. 18: Asano N, Yamauchi T, Kagamifuchi K, Shimizu N, Takahashi S, Takatsuka H, Ikeda K, Kizu H, Chuakul W, Kettawan A, Okamoto T. Iminosugar-producing Thai medicinal plants. J Nat Prod. 2005 Aug;68(8):1238-42. PubMed PMID: 16124768. 19: Magalhães AF, Santos CC, Magalhães EG, Nogueira MA. Detection of polyhydroxyalkaloids in Lonchocarpus extracts by GC-MS of acetylated derivatives. Phytochem Anal. 2002 Jul-Aug;13(4):215-21. PubMed PMID: 12184175. 20: Goujon JY, Gueyrard D, Compain P, Martin OR, Ikeda K, Kato A, Asano N. General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides). Bioorg Med Chem. 2005 Mar 15;13(6):2313-24. PubMed PMID: 15727880.