Raffinose
Names
IUPAC name
β-D-Fructofuranosyl α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside
Systematic IUPAC name
(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Other names
rafinosa
D-(+)-Raffinose
D-Raffinose
D-raffinose pentahydrate
Gossypose
Melitose
Melitriose
NSC 170228
NSC 2025
6G-α-D-galactosylsucrose;
β-D-fructofuranosyl-O-α-D-glucopyranosyl-(1→6)-α-D-galactopyranoside hydrate(1:5)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.407
EC Number
  • 208-146-9  checkY[ECHA]
  • (pentahydrate): 605-771-2
KEGG
UNII
  • InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1 checkY
    Key: MUPFEKGTMRGPLJ-ZQSKZDJDSA-N checkY
  • InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
    Key: MUPFEKGTMRGPLJ-ZQSKZDJDBO
  • Key: MUPFEKGTMRGPLJ-ZQSKZDJDSA-N
  • C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)O)O)O)O)O)O)O
Properties
C18H32O16
Molar mass 594.5 g/mol (pentahydrate)
Melting point 118 °C
203 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Raffinose is a trisaccharide composed of galactose, glucose, and fructose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL), an enzyme which in the lumen of the human digestive tract is only produced by bacteria in the large intestine. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. The enzyme does not cleave β-linked galactose, as in lactose.

Chemical properties

The raffinose family of oligosaccharides (RFOs) are alpha-galactosyl derivatives of sucrose, and the most common are the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous in the plant kingdom, being found in a large variety of seeds from many different families, and they rank second only to sucrose in abundance as soluble carbohydrates.

Raffinose typically crystallises as a pentahydrate white crystalline powder.[1] It is odorless and has a sweet taste approximately 10% that of sucrose.[2]

Biochemical properties

Energy source

It is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the α-GAL enzyme to break down RFOs. These oligosaccharides pass undigested through the stomach and small intestine. In the large intestine, they are fermented by bacteria that do possess the α-GAL enzyme and make short-chain fatty acids (SCFA)(acetic, propionic, butyric acids), as well as the flatulence commonly associated with eating beans and other vegetables. These SCFAs have been recently found to impart a number of health benefits. α-GAL is present in digestive aids such as the product Beano.

Disease relevance

Research has shown that the differential ability to utilize raffinose by strains of the bacteria Streptococcus pneumoniae, impacts their ability to cause disease and the nature of the disease.[3]

Uses

Procedures concerning cryopreservation have used raffinose to provide hypertonicity for cell desiccation prior to freezing.[4] Either raffinose or sucrose is used as a base substance for sucralose.

Raffinose is also used in:[2]

See also

Further reading

References

  1. ↑ Kawasaki, T.; Takahashi, M.; Kiyanagi, R.; Ohhara, T. (2022-12-01). "Rearrangement of hydrogen bonds in dehydrated raffinose tetrahydrate: a time-of-flight neutron diffraction study". Acta Crystallographica Section C: Structural Chemistry. 78 (12): 743–748. doi:10.1107/S2053229622010828. ISSN 2053-2296. PMID 36468557. S2CID 253698466.
  2. 1 2 "D(+)-Raffinose pentahydrate | 17629-30-0". www.chemicalbook.com. Retrieved 2019-08-19.
  3. ↑ Minhas, Vikrant; Harvey, Richard M.; McAllister, Lauren J.; Seemann, Torsten; Syme, Anna E.; Baines, Sarah L.; Paton, James C.; Trappetti, Claudia (2019-01-15). McDaniel, Larry S. (ed.). "Capacity To Utilize Raffinose Dictates Pneumococcal Disease Phenotype". mBio. 10 (1). doi:10.1128/mBio.02596-18. ISSN 2150-7511. PMC 6336424. PMID 30647157.
  4. ↑ Storey B., Noiles, E., Thompson, K. (1998). "Comparison of Glycerol, Other Polyols, Trehalose, and Raffinose to Provide a Defined Cryoprotectant Medium for Mouse Sperm Cryopreservation". Cryobiology. 37 (1): 46–58. doi:10.1006/cryo.1998.2097. PMID 9698429.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Zartl, Barbara; Silberbauer, Karina; Loeppert, Renate; Viernstein, Helmut; Praznik, Werner; Mueller, Monika (2018). "Fermentation of non-digestible raffinose family oligosaccharides and galactomannans by probiotics". Food & Function. 9 (3): 1638–1646. doi:10.1039/c7fo01887h. PMID 29465736.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.