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Raffinose

Names
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]oxymethyl]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-galactopyranosyl-(1→6)-α-D-glucopyranoside hydrate(1:5)
Identifiers
CAS Number	512-69-6 Y 17629-30-0 (pentahydrate) Y[ECHA]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16634 Y
ChEMBL	ChEMBL223844 N
ChemSpider	388379 Y
ECHA InfoCard	100.007.407
EC Number	208-146-9  Y[ECHA]
PubChem CID	439242
UNII	N5O3QU595M Y
InChI 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 Y Key: MUPFEKGTMRGPLJ-ZQSKZDJDSA-N Y 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
SMILES 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
Chemical formula	C18H32O16
Molar mass	504.438 g/mol (pentahydrate)
Melting point	118 °C
Solubility in water	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 YN ?)
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 not found in the human digestive tract. 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.

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.

Humans and other monogastric animals (pigs 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 fermented by gas-producing bacteria that do possess the α-GAL enzyme and make carbon dioxide, methane 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.

Procedures concerning cryopreservation have used raffinose to provide hypertonicity for cell desiccation prior to freezing.^[1] Either raffinose or sucrose is used as a base substance for sucralose.

See also

• Raffinose—raffinose alpha-galactosyltransferase

References