604-68-2

Basic information

• Product Name: Glucose pentaacetate
• Synonyms: Glucopyranose, pentaacetate, alpha-D-;1,2,3,4,6-PENTA-O-ACETYL-A-D-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-A-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-GLUCOPYRANOSE;1,2,3,4,6-PENTAACETYL-ALPHA-D-GLUCOSE;ALPHA-D-GLUCOPYRANOSE-PENTAACETATE;ALPHA-GLUCOSE PENTAACETATE
• CAS NO: 604-68-2
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 210-073-2
• Product Categories: chiral;Biochemistry;Glucose;O-Substituted Sugars;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives
• Mol File: 604-68-2.mol
• Article Data: 316

Chemical Properties

• Melting Point: 111-113 °C
• Boiling Point: 435.58°C (rough estimate)
• Flash Point: 188.1 °C
• Appearance: White to off-white/Powder
• Density: 1.3984 (rough estimate)
• Vapor Pressure: 0-0Pa at 20-50℃
• Refractive Index: 105.5 ° (C=1.5, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility: < 5 G/L (25℃)
• BRN: 98852
• CAS DataBase Reference: Glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Glucose pentaacetate(604-68-2)
• EPA Substance Registry System: Glucose pentaacetate(604-68-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 24/25-53-36/37-26-25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 604-68-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets. Only α-D-glucose pentaacetate caused an immediate increase in insulin output. The β-anomer of D-glucose pentaacetate first transiently inhibited insulin release, this initial effect being followed by a secondary rise in secretory rate.

Purification Methods

Crystallise it from MeOH, EtOH or three recrystallisations from 95% EtOH. [Wolfrom & Thompson Methods in Carbohydrate Chemistry II 212 1963, Academic Press, Beilstein 17/7 V 318.]

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12?,13-,14+,15+,16+/m1/s1

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 75474-03-2 p-nitrobenzoic acetic anhydride 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 78416-55-4 Benzyl-2,3-O-isopropyliden-5-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-ribofuranosid 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 64-19-7 acetic acid 
• 75172-83-7 3,4,6-Tri-O-acetyl-1,2-O-(1-<4-(4-biphenylyl)butyryloxy>ethyliden)-α-D-glucopyranose 
• 17460-45-6 tetra-acetyl glucosamine 
• 604-69-3 β-D-glucose pentaacetate 
• 67-56-1 methanol 

Downstream Products

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 
• 125354-48-5 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 6087-47-4 O³,O⁴,O⁶-triacetyl-O²-trichloroacetyl-β-D-mannopyranosyl chloride 
• 36215-42-6 N-<3,4,6-tri-O-acetyl-β-D-glucopyranosyl>piperidine 
• 14131-42-1 p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 84380-04-1 3-chlorophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 79444-24-9 2,3,4,6-tetra-O-acetyl-1-O-(2,4,6-trimethylbenzoyl)-α-D-glucopyranose 

Relevant articles and documents

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Isolation and characterization of triterpenoid saponins from leaves of Aralia nudicaulis L

Three new oleanolic glycosides (1–3), along with seven known saponins from various plants (4–10) were isolated for the first time from the leaves of Aralia nudicaulis. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, and HRESIMS. Nudicauloside A and B (1–2) have shown moderate anti-inflammatory activity, as demonstrated by inhibition of LPS-induced NO production in raw 264.7 murine macrophages (IC50 = 74–101 μM).