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Stachyose

Chemical compound From Wikipedia, the free encyclopedia

Stachyose is a tetrasaccharide consisting of two α-D-galactose units, one α-D-glucose unit, and one β-D-fructose unit sequentially linked as Gal(α1→6)Gal(α1→6)Glc(α1↔2β)Fruf.[1] Together with related oligosaccharides such as raffinose, stachyose occurs naturally in numerous vegetables (e.g. green beans, soybeans and other beans) and other plants.

Quick facts Names, Identifiers ...
Stachyose
Names
IUPAC name
β-D-Fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside
Systematic IUPAC name
(12S,13S,14S,15R,32R,33R,34S,35S,36R,62S,63R,64S,65R,66R,92S,93R,94S,95R,96R)-12,15,96-Tris(hydroxymethyl)-2,5,8-trioxa-3,6(2,6),9(2)-tris(oxana)-1(2)-oxolananonaphane-13,14,33,34,35,63,64,65,93,94,95-undecol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.754 Edit this at Wikidata
EC Number
  • 207-427-3
UNII
  • InChI=1S/C24H42O21/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24/h6-23,25-38H,1-5H2/t6-,7-,8-,9-,10+,11+,12-,13-,14+,15+,16+,17-,18-,19-,20+,21+,22+,23-,24+/m1/s1 checkY
    Key: UQZIYBXSHAGNOE-XNSRJBNMSA-N checkY
  • 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)OC[C@@H]3[C@H]([C@@H]([C@H]([C@H](O3)O[C@]4([C@H]([C@@H]([C@H](O4)CO)O)O)CO)O)O)O)O)O)O)O)O)O)O
Properties
C24H42O21
Molar mass 666.578 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Stachyose is less sweet than sucrose, at about 28% on a weight basis. It is mainly used as a bulk sweetener or for its functional oligosaccharide properties.[2][additional citation(s) needed] Stachyose is not completely digestible by humans and delivers 1.5 to 2.4 kcal/g (6 to 10 kJ/g).

Biosynthesis

In plants such as Vicia faba, stachyose is biosynthesized from the trisaccharide, raffinose, by the enzyme galactinol-raffinose galactosyltransferase. This uses galactinol as the source of the galactose unit, with inositol (myo-inositol) as a byproduct.[3] [4]

2D representation of the chemical structure of Q27102430.
galactinol
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