Raffinose

Raffinose
Names
	Preferred 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 ; 17629-30-0 (pentahydrate) [ECHA];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16634 ;
ChemSpider	388379 ;
ECHA InfoCard	100.007.407
EC Number	208-146-9 [ECHA];
PubChem CID	439242;
UNII	N5O3QU595M ;
CompTox Dashboard (EPA)	DTXSID8041111 ;
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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).
	(what is ?)
	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 not found in the human digestive tract. α-GAL also hydrolyzes other such as stachyose, , and , if present. The enzyme does not cleave β-linked galactose, as in lactose.

Chemical properties[]

The raffinose family of oligosaccharides (RFOs) are alpha-galactosyl derivatives of sucrose, and the most common are the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous in the plant kingdom, being found in a large variety of seeds from many different families, and they rank second only to sucrose in abundance as .

Raffinose may have a form of a white crystalline powder. It is odorless and has a sweet taste approximately 10% that of sucrose.^[1]

Biochemical properties[]

Energy source[]

It is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the α-GAL enzyme to break down RFOs. These oligosaccharides pass undigested through the stomach and small intestine. In the large intestine, they are fermented by bacteria that do possess the α-GAL enzyme and make short-chain fatty acids (SCFA)(acetic, propionic, butyric acids), as well as the flatulence commonly associated with eating beans and other vegetables. These SCFAs have been recently found to impart a number of health benefits. α-GAL is present in digestive aids such as the product Beano.

Disease relevance[]

Research has shown that the differential ability to utilize raffinose by strains of the bacteria Streptococcus pneumoniae, impacts their ability to cause disease.^[2]

Uses[]

Procedures concerning cryopreservation have used raffinose to provide hypertonicity for cell desiccation prior to freezing.^[3] Either raffinose or sucrose is used as a base substance for sucralose.

Raffinose is also used in:^[1]

skin moisturizers and smoothers
prebiotics (it allegedly promotes growth of lactobacilli and bifidobacteria)^[4]
food or drinks additive

References[]

^ Jump up to: ^a ^b "D(+)-Raffinose pentahydrate | 17629-30-0". www.chemicalbook.com. Retrieved 2019-08-19.
^ Minhas, Vikrant; Harvey, Richard M.; McAllister, Lauren J.; Seemann, Torsten; Syme, Anna E.; Baines, Sarah L.; Paton, James C.; Trappetti, Claudia (2019-01-15). McDaniel, Larry S. (ed.). "Capacity To Utilize Raffinose Dictates Pneumococcal Disease Phenotype". mBio. 10 (1). doi:10.1128/mBio.02596-18. ISSN 2150-7511.
^ Storey B., Noiles, E., Thompson, K. (1998). "Comparison of Glycerol, Other Polyols, Trehalose, and Raffinose to Provide a Defined Cryoprotectant Medium for Mouse Sperm Cryopreservation". Cryobiology. 37 (1): 46–58. doi:10.1006/cryo.1998.2097. PMID 9698429.CS1 maint: multiple names: authors list (link)
^ Zartl B, Silberbauer K, Loeppert R, Viernstein H, Praznik W, Mueller M. Fermentation of non-digestible raffinose family oligosaccharides and galactomannans by probiotics. Food Funct. 2018 Mar 1;9(3):1638-1646. doi: 10.1039/c7fo01887h. Epub 2018 Feb 21. PMID: 29465

[:0-1] Jump up to: ^a ^b "D(+)-Raffinose pentahydrate | 17629-30-0". www.chemicalbook.com. Retrieved 2019-08-19.

[2] Minhas, Vikrant; Harvey, Richard M.; McAllister, Lauren J.; Seemann, Torsten; Syme, Anna E.; Baines, Sarah L.; Paton, James C.; Trappetti, Claudia (2019-01-15). McDaniel, Larry S. (ed.). "Capacity To Utilize Raffinose Dictates Pneumococcal Disease Phenotype". mBio. 10 (1). doi:10.1128/mBio.02596-18. ISSN 2150-7511.

[3] Storey B., Noiles, E., Thompson, K. (1998). "Comparison of Glycerol, Other Polyols, Trehalose, and Raffinose to Provide a Defined Cryoprotectant Medium for Mouse Sperm Cryopreservation". Cryobiology. 37 (1): 46–58. doi:10.1006/cryo.1998.2097. PMID 9698429.CS1 maint: multiple names: authors list (link)

[:1-4] Zartl B, Silberbauer K, Loeppert R, Viernstein H, Praznik W, Mueller M. Fermentation of non-digestible raffinose family oligosaccharides and galactomannans by probiotics. Food Funct. 2018 Mar 1;9(3):1638-1646. doi: 10.1039/c7fo01887h. Epub 2018 Feb 21. PMID: 29465

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