| Record Information |
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| Version | 1.0 |
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| Created at | 2006-05-22 15:12:41 UTC |
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| Updated at | 2024-04-19 10:02:29 UTC |
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| NP-MRD ID | NP0000023 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Raffinose |
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| Description | Raffinose is a complex carbohydrate. It is a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose is hydrolyzed to D-galactose and sucrose by D-galactosidase (D-GAL). D-GAL also hydrolyzes other D-galactosides such as stachyose, verbascose, and galactinol [1-O-(D-galactosyl)-myoinositol], if present. The enzyme does not cleave linked galactose, as in lactose. Raffinose is also known as melitose and may be thought of as galactose and sucrose connected via an alpha(1->6) glycosidic linkage. Thus, raffinose can be broken down into galactose and sucrose via the enzyme alpha-galactosidase. Human intestines do not contain this enzyme. Raffinose is a trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 6g-alpha-D-Galactosylsucrose | ChEBI | | alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside | ChEBI | | alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-fruf | ChEBI | | Gossypose | ChEBI | | Melitose | ChEBI | | Melitriose | ChEBI | | Rafinose | ChEBI | | Raflinose | ChEBI | | 6g-a-D-Galactosylsucrose | Generator | | 6g-Α-D-galactosylsucrose | Generator | | a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranoside | Generator | | Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranoside | Generator | | a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-fruf | Generator | | Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-fruf | Generator | | D-(+)-Raffinose | HMDB | | D-Raffinose | HMDB | | beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranoside | HMDB | | Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside | HMDB | | Raffinose | HMDB |
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| Chemical Formula | C18H32O16 |
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| Average Mass | 504.4371 Da |
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| Monoisotopic Mass | 504.16903 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 512-69-6 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1 |
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| InChI Key | MUPFEKGTMRGPLJ-ZQSKZDJDSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-02 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-02 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-02 | View Spectrum | | 1D NMR | [13C, ] NMR Spectrum (2D, 201 MHz, C2D6OS, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-02 | View Spectrum | | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-02 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Oligosaccharides |
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| Alternative Parents | |
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| Substituents | - Oligosaccharide
- C-glycosyl compound
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Oxane
- Tetrahydrofuran
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 80 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 203 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | Not Available |
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| General References | - Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7. [PubMed:16187674 ]
- Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
- Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
- Toussaint M, Latger-Cannard V, Caron A, Lecompte T, Vigneron C, Menu P: Hemoglobin-based oxygen carriers do not alter platelet functions: study of three chemically modified hemoglobin solutions. Intensive Care Med. 2003 Jan;29(1):62-8. Epub 2002 Nov 30. [PubMed:12528024 ]
- Xue S, Paterson W, Valdez D, Miller D, Christoff B, Wong LT, Diamant NE: Effect of an o-raffinose cross-linked haemoglobin product on oesophageal and lower oesophageal sphincter motor function. Neurogastroenterol Motil. 1999 Dec;11(6):421-30. [PubMed:10583849 ]
- Persson AE, Schnermann J, Agerup B, Eriksson NE: The hydraulic conductivity of the rat proximal tubular wall determined with colloidal solutions. Pflugers Arch. 1975 Oct 16;360(1):25-44. [PubMed:1237863 ]
- Hessels J, Snoeyink EJ, Platenkamp AJ, Voortman G, Steggink J, Eidhof HH: Assessment of intestinal permeability: enzymatic determination of urinary mannitol, raffinose, sucrose and lactose on Hitachi analyzer. Clin Chem Lab Med. 2003 Jan;41(1):33-8. [PubMed:12636047 ]
- Horodniceanu T, Delbos F: [Group D streptococci in human infections: identification and sensitivity to antibiotics (author's transl)]. Ann Microbiol (Paris). 1980 Sep-Oct;131B(2):131-44. [PubMed:7458116 ]
- Lieberthal W, Fuhro R, Alam H, Rhee P, Szebeni J, Hechtman HB, Favuzza J, Veech RL, Valeri CR: Comparison of the effects of a 50% exchange-transfusion with albumin, hetastarch, and modified hemoglobin solutions. Shock. 2002 Jan;17(1):61-9. [PubMed:11795671 ]
- Gundermann KJ, Lie TS: Problems of competition in charcoal hemoperfusion for the treatment of intoxications. Artif Organs. 1979 Nov;3(4):346-9. [PubMed:533425 ]
- Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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