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604-68-2 molecular structure
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[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate

ChemBase ID: 102174
Molecular Formular: C16H22O11
Molecular Mass: 390.33928
Monoisotopic Mass: 390.11621152
SMILES and InChIs

SMILES:
O=C(O[C@H]1O[C@@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C)C
Canonical SMILES:
CC(=O)OC[C@H]1O[C@H](OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
InChI:
InChI=1S/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
InChIKey:
LPTITAGPBXDDGR-LJIZCISZSA-N

Cite this record

CBID:102174 http://www.chembase.cn/molecule-102174.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
IUPAC Traditional name
[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
Synonyms
α-D(+)-Glucose pentaacetate
α-D(+)-Glucose pentaacetate
1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose
Glucose pentaacetate
α-D-Glucopyranose 1,2,3,4,6-Pentaacetate
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Acetate
NSC 119335
NSC 9290
α-D-Glucopyranosyl Pentaacetate
α-D-Glucose Pentaacetate
1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose
α-D-GLUCOSE PENTAACETATE
α-D-(+)-Glucose pentaacetate
1,2,3,4,6-Pentaacetyl-alpha-D-glucose
alpha-D-Glucose pentaacetate
1,2,3,4,6-α-D(+)-葡萄糖五乙酸酯
1,2,3,4,6-α-D(+)-葡萄糖五乙酸酯
葡萄糖五乙酸酯
1,2,3,4,6-五-O-乙酰基-α-D-吡喃葡萄糖
1,2,3,4,6-α-D-(+)-葡萄糖五乙酸酯
α-D-葡糖五乙酸酯
CAS Number
604-68-2
EC Number
210-073-2
MDL Number
MFCD00064071
Beilstein Number
98852
PubChem SID
24900987
24872709
162088374
24895094
PubChem CID
2723636
FEMA ID
2524
Council of Europe Number
2524c

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.72691214  LogD (pH = 7.4) -0.72691214 
Log P -0.72691214  Molar Refractivity 81.6809 cm3
Polarizability 34.419 Å3 Polar Surface Area 140.73 Å2
Rotatable Bonds 11  Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
chloroform: soluble0.1 g/mL, clear, colorless expand Show data source
Melting Point
109-111 °C(lit.) expand Show data source
109-111°C expand Show data source
109-113°C expand Show data source
111-113 °C expand Show data source
Optical Rotation
[α]20/D +100±2°, c = 5% in chloroform expand Show data source
[α]20/D +102°, c = 1 in chloroform expand Show data source
[α]20/D +98°, c = 1 in chloroform expand Show data source
+102 (c=5 in chloroform) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥99% expand Show data source
≥99.0% (sum of enantiomers, GC) expand Show data source
99% expand Show data source
Grade
for microbiology expand Show data source
Kosher expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C16H22O11 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - G2354 external link
Packaging
25, 100 g in poly bottle
Sigma Aldrich - 49200 external link
Other Notes
Selective 1-O-deacetylation1
Toronto Research Chemicals - G596495 external link
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, th

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Carpinelli, A., et al.: Mol. Cell Endocrinol., 17, 103 (1980)
  • • Hellman, B., et al.: Diab. Metab., 20, 123 (1980)
  • • Malaisse, W., et al.: Int. J. Mol. Med., 2, 331 (1980)
  • • Sener, A., et al.: Mol. Gen. Metab., 64, 135 (1980)
  • • Regioselective 1-O-deacylation can be effected with ammonia in acetonitrile at ambient temperature: Synthesis, 1121 (1985).
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PATENTS

PATENTS

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INTERNET

INTERNET

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