Description
D-
(+)-
Raffinose is a trisaccharide composed of galactose, glucose, and fructose that occurs naturally in a variety of vegetables and grains. It is hydrolyzed to galactose and sucrose by α-
galactosidase.
Chemical Properties
Raffinose is a white crystalline powder. It is odorless and has a sweet
taste approximately 10% that of sucrose.
Uses
D-(+)-Raffinose is a trisaccharide built from 1 mol each of D-galactose, D-glucose, and D-fructose which are obtained from it by acid hydrolysis. Invertase splits it into melibiose and saccharose. D-(+)-Raffinose occurs in Australian manna; in cottonseed meal.
Uses
moisturizes and smoothes skin, prevents skin ageing, promotes skin regeneration: non-digestible with lower efficiency than lactose or sucrose; prebiotic stimulates growth of lactobacilli and bifidobacteria; additive in low-cariogenic food or drinks
Production Methods
Raffinose occurs naturally in Australian manna, cottonseed meal,
and seeds of various food legumes. It can be isolated from beet sugar
molasses through sucrose separation, seed-crystallization, and
filtration.
Pharmaceutical Applications
Raffinose is a trisaccharide carbohydrate that is used as a bulking
agent, blood substitute, stabilizing agent, and water scavenger in
freeze-drying where it acts as a stabilizer for freeze-dried formulations. It is also used as a crystallization inhibitor in sucrose
solutions.
Biochem/physiol Actions
Raffinose is a trisaccharide composed of galactose, fructose, and glucose. Raffinose is hydrolysed to D-galactose and sucrose by D-galactosidase.
Safety
Raffinose is a naturally occurring trisaccharide investigated for use
in freeze-dried pharmaceutical formulations. It occurs in a number
of plants that are consumed widely.
storage
Raffinose is stable under ordinary conditions of use and storage.
Excessive heat should be avoided to prevent degradation. Thermal decomposition products are carbon monoxide and carbon dioxide.
Purification Methods
fructo-furanose [17629-30-0 (5H2O), 512-69-6 (anhydrous)] M 594.5, m 8 0o, 80 -82o, +124o (c 10, H2O), [ ] D +105o (c 1 for pentahydrate, H2O), pK 1 12.40, pK 2 13.44, pK 3 13.52. D(+)-Raffinose crystallises from H2O, 90% aqueous EtOH or MeOH as the pentahydrate. The anhydrous sugar has m 132-135o. It has RF 0.8 on TLC (Silica Gel, and 1:3:3 CHCl3/butanone:/MeOH). The undecaacetate has been purified through an alumina column by elution with CHCl3, and recrystallised from EtOH/MeOH/H2O (3:2:5), with m 99-100o, [] D +92.8o (c 5.14, EtOH). [pK : Coccioli & Vicedomini Ann Chim (Rome) 66 269, 275 1976, 1H NMR: Suami et al. Carbohydr Research 26 234 1973, Beilstein 17 III/IV 3801, 17/8 V 403.]
Incompatibilities
Raffinose is incompatible with strong oxidizers.
Regulatory Status
Raffinose is a naturally occurring trisaccharide and is consumed as
part of a normal diet.
