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MedKoo Cat#: 146297 | Name: Melibiose

Description:

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

Melibiose is a disaccharide composed of galactose and glucose linked by an α-1,6-glycosidic bond. It is formed during the enzymatic hydrolysis of raffinose by the enzyme invertase. Melibiose is used in microbiological media to study carbohydrate metabolism and to differentiate microbial species based on their ability to ferment it. Its digestion in organisms capable of utilizing it involves the enzyme α-galactosidase, which breaks the glycosidic bond to release the monosaccharides.

Chemical Structure

Melibiose
Melibiose
CAS#585-99-9

Theoretical Analysis

MedKoo Cat#: 146297

Name: Melibiose

CAS#: 585-99-9

Chemical Formula: C12H22O11

Exact Mass: 342.1162

Molecular Weight: 342.30

Elemental Analysis: C, 42.11; H, 6.48; O, 51.41

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Melibiose;
IUPAC/Chemical Name
(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal
InChi Key
AYRXSINWFIIFAE-GFRRCQKTSA-N
InChi Code
1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9-,10-,11+,12-/m0/s1
SMILES Code
OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@@H](O)[C@H]1O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 342.30 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.

Recalculate based on batch purity %
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: Pourcher T, Bassilana M, Sarkar HK, Kaback HR, Leblanc G. The melibiose/Na+ symporter of Escherichia coli: kinetic and molecular properties. Philos Trans R Soc Lond B Biol Sci. 1990 Jan 30;326(1236):411-23. doi: 10.1098/rstb.1990.0021. PMID: 1970646. 2: Botfield MC, Wilson DM, Wilson TH. The melibiose carrier of Escherichia coli. Res Microbiol. 1990 Mar-Apr;141(3):328-31. doi: 10.1016/0923-2508(90)90006-c. PMID: 2281192. 3: Denner C, Gintner M, Kählig H, Schmid W. Indium-mediated C-allylation of melibiose. Beilstein J Org Chem. 2019 Oct 16;15:2458-2464. doi: 10.3762/bjoc.15.238. PMID: 31666880; PMCID: PMC6808214. 4: Wu Z, Zhang Y, Liu Y, Chen X, Huang Z, Zhao X, He H, Deng Y. Melibiose Confers a Neuroprotection against Cerebral Ischemia/Reperfusion Injury by Ameliorating Autophagy Flux via Facilitation of TFEB Nuclear Translocation in Neurons. Life (Basel). 2021 Sep 10;11(9):948. doi: 10.3390/life11090948. PMID: 34575099; PMCID: PMC8465207. 5: Staniszewska M, Bronowicka-Szydełko A, Gostomska-Pampuch K, Szkudlarek J, Bartyś A, Bieg T, Gamian E, Kochman A, Picur B, Pietkiewicz J, Kuropka P, Szeja W, Wiśniewski J, Ziółkowski P, Gamian A. The melibiose-derived glycation product mimics a unique epitope present in human and animal tissues. Sci Rep. 2021 Feb 3;11(1):2940. doi: 10.1038/s41598-021-82585-7. PMID: 33536563; PMCID: PMC7859244. 6: Hariharan P, Guan L. Cooperative binding ensures the obligatory melibiose/Na+ cotransport in MelB. J Gen Physiol. 2021 Aug 2;153(8):e202012710. doi: 10.1085/jgp.202012710. Epub 2021 Jun 10. PMID: 34110360; PMCID: PMC8200842. 7: Blaimschein N, Hariharan P, Manioglu S, Guan L, Müller DJ. Substrate-binding guides individual melibiose permeases MelB to structurally soften and to destabilize cytoplasmic middle-loop C3. Structure. 2023 Jan 5;31(1):58-67.e4. doi: 10.1016/j.str.2022.11.011. Epub 2022 Dec 15. PMID: 36525976; PMCID: PMC9825662. 8: Palomäki EAK, Lipiäinen T, Strachan CJ, Yliruusi JK. Effect of trehalose and melibiose on crystallization of amorphous paracetamol. Int J Pharm. 2020 Nov 30;590:119878. doi: 10.1016/j.ijpharm.2020.119878. Epub 2020 Sep 12. PMID: 32927005. 9: Tanaka S, Shinoki A, Hara H. Melibiose, a Nondigestible Disaccharide, Promotes Absorption of Quercetin Glycosides in Rat Small Intestine. J Agric Food Chem. 2016 Dec 14;64(49):9335-9341. doi: 10.1021/acs.jafc.6b03714. Epub 2016 Dec 5. PMID: 27794607. 10: Tamura C, Matsushita O. Melibiose transport system in Lactobacillus plantarum. Microbiol Immunol. 1992;36(11):1119-28. doi: 10.1111/j.1348-0421.1992.tb02116.x. PMID: 1337134. 11: Chen CM, Lin CH, Wu YR, Yen CY, Huang YT, Lin JL, Lin CY, Chen WL, Chao CY, Lee-Chen GJ, Su MT, Chang KH. Lactulose and Melibiose Inhibit α-Synuclein Aggregation and Up-Regulate Autophagy to Reduce Neuronal Vulnerability. Cells. 2020 May 16;9(5):1230. doi: 10.3390/cells9051230. PMID: 32429337; PMCID: PMC7290909. 12: Venkatesh A, Murray AL, Coughlan AY, Wolfe KH. Giant GAL gene clusters for the melibiose-galactose pathway in Torulaspora. Yeast. 2021 Jan;38(1):117-126. doi: 10.1002/yea.3532. Epub 2020 Dec 7. PMID: 33141945; PMCID: PMC7898345. 13: Leblanc G, Pourcher T, Zani ML. The melibiose permease of Escherichia coli: importance of the NH2-terminal domains for cation recognition by the Na+/sugar cotransporter. Soc Gen Physiol Ser. 1993;48:213-27. PMID: 8099233. 14: Markham KJ, Tikhonova EB, Scarpa AC, Hariharan P, Katsube S, Guan L. Complete cysteine-scanning mutagenesis of the Salmonella typhimurium melibiose permease. J Biol Chem. 2021 Sep;297(3):101090. doi: 10.1016/j.jbc.2021.101090. Epub 2021 Aug 18. PMID: 34416232; PMCID: PMC8437787. 15: Katsube S, Liang R, Amin A, Hariharan P, Guan L. Molecular Basis for the Cation Selectivity of Salmonella typhimurium Melibiose Permease. J Mol Biol. 2022 Jun 30;434(12):167598. doi: 10.1016/j.jmb.2022.167598. Epub 2022 Apr 22. PMID: 35461877; PMCID: PMC9177823. 16: Gostomska-Pampuch K, Wiśniewski JR, Sowiński K, Gruszecki WI, Gamian A, Staniszewska M. Analysis of the Site-Specific Myoglobin Modifications in the Melibiose-Derived Novel Advanced Glycation End-Product. Int J Mol Sci. 2022 Oct 27;23(21):13036. doi: 10.3390/ijms232113036. PMID: 36361822; PMCID: PMC9655033. 17: Tanaka K, Niiya S, Tsuchiya T. Melibiose transport of Escherichia coli. J Bacteriol. 1980 Mar;141(3):1031-6. doi: 10.1128/jb.141.3.1031-1036.1980. PMID: 6988398; PMCID: PMC293773. 18: Santalova EA, Denisenko VA, Dmitrenok PS, Ha DT, Hung NA, Drozdov AL, Malyarenko OS, Thuy TTT, Quan PM, Long PQ. Occurrence of Melibiose-Containing Glycosphingolipids in a Sample of a Sponge-Coral Association (Desmapsamma anchorata/Carijoa riisei). Chem Biodivers. 2019 Jan;16(1):e1800401. doi: 10.1002/cbdv.201800401. Epub 2019 Jan 17. PMID: 30417533. 19: Katsube S, Willibal K, Vemulapally S, Hariharan P, Tikhonova E, Pardon E, Kaback HR, Steyaert J, Guan L. In vivo and in vitro characterizations of melibiose permease (MelB) conformation-dependent nanobodies reveal sugar-binding mechanisms. J Biol Chem. 2023 Aug;299(8):104967. doi: 10.1016/j.jbc.2023.104967. Epub 2023 Jun 26. PMID: 37380079; PMCID: PMC10374971. 20: Ethayathulla AS, Yousef MS, Amin A, Leblanc G, Kaback HR, Guan L. Structure- based mechanism for Na(+)/melibiose symport by MelB. Nat Commun. 2014;5:3009. doi: 10.1038/ncomms4009. PMID: 24389923; PMCID: PMC4026327.