546-62-3

Basic information

• Product Name: VERBASCOSE
• Synonyms: α-d-galp-(1→6)-α-d-galp-(1→6)-α-d-galp-(1→6)-α-d-glup(1←→2)-β-d-fruf;α-D-Galp-(1-6)-α-D-Galp-(1-6)-α-D-Galp-(1-6)-α-D-Glup(1↔:2)-β-D-Fruf;β-D-Fructofuranosyl 6-O-[6-O-[6-O-(α-D-galactopyranosyl)-α-D-galactopyranosyl]-α-D-galactopyranosyl]-α-D-glucopyranoside;(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-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-3,4,5-triol;(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-dimethylol-tetrahydrofuran-2-yl]oxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-3,4,5-triol;Verbascose,α-D-Galp-(1→6)-α-D-Galp-(1→6)-α-D-Galp-(1→6)-α-D-Glup(12)-β-D-Fruf
• CAS NO: 546-62-3
• Molecular Formula: C₃₀H₅₂O₂₆
• Molecular Weight: 828.715
• EINECS: 208-905-4
• Mol File: 546-62-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 219-220°; mp 253°
• Boiling Point: 1185°Cat760mmHg
• Flash Point: 670.5°C
• Appearance: /
• Density: 1.86g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.699
• PKA: 12.81±0.70(Predicted)
• CAS DataBase Reference: VERBASCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: VERBASCOSE(546-62-3)
• EPA Substance Registry System: VERBASCOSE(546-62-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 546-62-3(Hazardous Substances Data)

Usage

Description

VERBASCOSE, also known as verbascifolin, is an α-galactooligosaccharide that is widely present in legumes. It is indigestible by humans due to the lack of α-galactosidase, which leads to fermentation in the colon and the production of gases such as CO2, H2, and CH4, commonly associated with flatulence. VERBASCOSE also exhibits immunomodulatory activity in mouse macrophage RAW264.7 cells.

Uses

Used in Pharmaceutical Industry:
VERBASCOSE is used as an immunomodulatory agent for its ability to modulate the immune response in mouse macrophage RAW264.7 cells. This property makes it a potential candidate for the development of drugs targeting immune system-related conditions.
Used in Nutrition and Digestive Health:
VERBASCOSE is used as a prebiotic for promoting the growth of beneficial bacteria in the colon. Its fermentation in the colon produces gases like CO2, H2, and CH4, which can be utilized by certain gut bacteria, thus contributing to a healthy gut microbiota and potentially aiding in digestive health.

InChI:InChI=1/C30H52O26/c31-1-7-12(34)17(39)21(43)26(51-7)48-3-9-13(35)18(40)22(44)27(52-9)49-4-10-14(36)19(41)23(45)28(53-10)50-5-11-15(37)20(42)24(46)29(54-11)56-30(6-33)25(47)16(38)8(2-32)55-30/h7-29,31-47H,1-6H2/t7-,8-,9-,10-,11-,12+,13+,14+,15-,16-,17+,18+,19+,20+,21-,22-,23-,24-,25+,26+,27+,28+,29-,30+/m1/s1

Upstream product

• 512-69-6 D-raffinose 

Relevant articles and documents

Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system

A convenient approach for synthesis of raffinose, stachyose, and verbascose using sucrose as the starting material is presented. The key step is the regioselective de-O-benzylation with Co2(CO)8/Et 3SiH/CO system, followed by a high α-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose substrate is achieved in high yield.