Raffinose
1856589
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2008-06-28T13:44:00Z
Arcadian
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| ImageSize = 275px
| IUPACName = <small>(''2R,3R,4S,5S,6R'')-2-[(''2S,3S,4S,5R'')-3,4- Dihydroxy-2,5-bis(hydroxymethyl)<br>oxolan-2-yl]oxy-6-[ [(''2S,3R,4S,5R,6R'')-3,4,5-trihydroxy-6- (hydroxymethyl)oxan-2-yl]oxymethyl]<br>oxane-3,4,5-triol</small>| OtherNames = Melitose<br>Melitriose<br>Gossypose<br>α-D-Galactosylsucrose
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| CASNo = 512-69-6
| CASOther = <br>{{CASREF|CAS=7629-30-0}} (pentahydrate)
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| PubChem = 439242
| SMILES = C([C@@H]1[C@@H]([C@@H]([C@H]<br/>([C@H](O1)OC[C@@H]2[C@H]([C@@H]<br/>([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]<br/>([C@H](O3)CO)O)O)CO)O)O)O)O)O)O)O
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| Section2 = {{Chembox Properties
| Formula = C<sub>18</sub>H<sub>32</sub>O<sub>16</sub>
| MolarMass = 504.42 g/mol
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| Section7 = {{Chembox Hazards
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'''Raffinose''' is a [[trisaccharide]] composed of [[galactose]], [[fructose]], and [[glucose]]. It can be found in [[bean]]s, [[cabbage]], [[brussels sprout]]s, [[broccoli]], [[asparagus]], other [[vegetables]], and whole [[grain]]s. Raffinose can be [[hydrolysis|hydrolyzed]] to D-galactose and [[sucrose]] by the enzyme [[alpha galactosidase|α-galactosidase]] (α-GAL), an enzyme not found in humans. α-GAL also hydrolyzes other [[alpha galactoside|α-galactosides]] such as [[stachyose]], [[verbascose]], and [[galactinol]], if present. The enzyme does not cleave β-linked galactose, as in [[lactose]].
The raffinose family of [[oligosaccharide]]s (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]].
Humans and other monogastric animals ([[pig]]s and [[poultry]]) do not possess the α-GAL enzyme to break down RFOs and these oligosaccharides pass undigested through the stomach and upper intestine. In the lower intestine, they are [[fermentation (biochemistry)|fermented]] by gas-producing [[bacteria]] which do possess the α-GAL enzyme and make [[carbon dioxide]], [[methane]], and/or [[hydrogen]] -- leading to the [[flatulence]] commonly associated with eating beans and other vegetables. α-GAL is present in digestive aids such as the product [[Beano (dietary supplement)|Beano]].
Procedures concerning cryopreservation have utilized raffinose to provide hypertonicity for cell desiccation prior to freezing <ref>{{cite journal| author=Storey B., Noiles, E., Thompson, K. | title=Comparison of Glycerol, Other Polyols, Trehalose, and Raffinose to Progive a defined cryoprotectant Medium for Mouse Sperm Cryopreservation|journal= Cryobiology|volume= 37| pages=46–58 |year=1998 | doi=10.1006/cryo.1998.2097}}</ref>. Either raffinose or [[sucrose]] is used as a base substance for [[sucralose]].
==See also==
* [[Raffinose-raffinose alpha-galactosyltransferase]]
==References==
{{Reflist}}
{{Carbohydrates}}
[[Category: Carbohydrates]]
[[Category: Oligosaccharides]]
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