Stachyose

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
CAS Number	470-55-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17164 ;
ChemSpider	388624 ;
ECHA InfoCard	100.006.754
EC Number	207-427-3;
PubChem CID	91455; 439531;
UNII	25VX64653N ;
CompTox Dashboard (EPA)	DTXSID30889345 ;
	InChI 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 Key: UQZIYBXSHAGNOE-XNSRJBNMSA-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)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
Chemical formula	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). Infobox references

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.

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]