raffinose

Also known as alpha-D-Galp-(1->6)-alpha-D-Glcp-(1<->2)-beta-D-Fruf, alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside, raflinose, rafinose, (2R,3R,4S,5R,6R)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]oxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3,4,5-triol, (2R,3R,4S,5R,6R)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-3,4,5-triol, (2R,3R,4S,5R,6R)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-2,5-dimethylol-tetrahydrofuran-2-yl]oxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3,4,5-triol, Raffinose hydrate

Raffinose is a trisaccharide derived from galactose, glucose, and fructose. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme alpha galactosidase (α-GAL), an enzyme synthesized by bacteria found in the large intestine. α-GAL also hydrolyzes other alpha 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. It can be found in beans, cabbage, Brussels sprouts, broccoli, asparagus, other vegetables, and

Chemical data

Formula: C18H32O16
Molecular weight: 504.4 g/mol
IUPAC name: (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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
InChIKey: MUPFEKGTMRGPLJ-ZQSKZDJDSA-N
XLogP: -5.8
Polar surface area: 269 Å²
H-bond donors: 11
H-bond acceptors: 16
Formal charge: 0

via PubChem

Research

5,285 papers

via PubMed

Wikidata facts

Mass: 504.169

Show 4 more facts

chemical formula: C₁₈H₃₂O₁₆
canonical SMILES: C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3(C(C(C(O3)CO)O)O)CO)O)O)O)O)O)O)O
isomeric 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
Commons category: Raffinose

Sources (4)

via Wikidata · CC0

~5 min read

Article

9 sections

Contents

Chemical properties
Biochemical properties
Energy source
Plant health
Disease relevance
Uses
See also
Further reading
References

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464379815 | ImageFile = Raffinose.svg | ImageFile2 = Raffinose-3D-balls.png | ImageSize = 275px | IUPACName = β-D-Fructofuranosyl α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside | SystematicName = (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 | OtherNames = 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)

|Section1=