Raffinose

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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
CAS Number	512-69-6 Y (pentahydrate): 17629-30-0 Y[ECHA]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16634 Y
ChEMBL	ChEMBL603717 N
ChemSpider	388379 Y
ECHA InfoCard	100.007.407
EC Number	208-146-9  Y[ECHA] (pentahydrate): 605-771-2
KEGG	C00492
PubChem CID	439242
UNII	N5O3QU595M Y
CompTox Dashboard (EPA)	DTXSID8041111
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	594.5 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 synthesized by bacteria found in the large intestine. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. In plants, raffinose plays a significant role in stress responses, particularly temperature sensitivity, seed vigour, resistance to pathogens, and desiccation.