CAS 604-68-2|[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate|[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate|1,2,3,4,6-Penta-O-acetyl-α-D-glucopyran...

General Information

Structure

Molecular Formula

C₁₆H₂₂O₁₁

Molecular Mass

390.33928

Exact Mass

390.11621152

Charge

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

Canonic 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

Isomeric 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

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

Polarizability

34.419

Polar Surface Area

140.73

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranoseα-D-GLUCOSE PENTAACETATE1,2,3,4,6-α-D-(+)-葡萄糖五乙酸酯1,2,3,4,6-五-O-乙酰基-α-D-吡喃葡萄糖α-D-(+)-Glucose pentaacetate1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose葡萄糖五乙酸酯α-D(+)-Glucose pentaacetate1,2,3,4,6-α-D(+)-葡萄糖五乙酸酯Glucose pentaacetateα-D(+)-Glucose pentaacetate1,2,3,4,6-α-D(+)-葡萄糖五乙酸酯NSC 119335α-D-Glucopyranose 1,2,3,4,6-Pentaacetate2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Acetateα-D-Glucopyranosyl PentaacetateNSC 9290α-D-Glucose Pentaacetate1,2,3,4,6-Pentaacetyl-alpha-D-glucoseα-D-葡糖五乙酸酯alpha-D-Glucose pentaacetate

Names and Identifiers

Registration numbers

EC Number

210-073-2

CAS Number

604-68-2

PubChem CID

2723636

PubChem SID

162088374248950942490098724872709

MDL Number

MFCD00064071

Beilstein Number

98852

FEMA ID

2524

Council of Europe Number

2524c

Registration numbers

Properties

Safety Information

Storage Condition

Room Temperature (15-30°C)

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

TSCA Listed

是

Physical Property

Melting Point

109-111°C

109-111 °C(lit.)

111-113 °C

109-113°C

Optical Rotation

[α]20/D +98°, c = 1 in chloroform

[α]20/D +102°, c = 1 in chloroform

[α]20/D +100±2°, c = 5% in chloroform

+102 (c=5 in chloroform)

chloroform: soluble0.1 g/mL, clear, colorless

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02100470

Crystalline

Sigma Aldrich

G2354

Packaging
25, 100 g in poly bottle

49200

Other Notes
Selective 1-O-deacetylation1

TRC

G596495

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

Molecule Details

References

PubChem Literature

From Data Sources

• Hellman, B., et al.: Diab. Metab., 20, 123 (1980)

• Carpinelli, A., et al.: Mol. Cell Endocrinol., 17, 103 (1980)

• Sener, A., et al.: Mol. Gen. Metab., 64, 135 (1980)

• Malaisse, W., et al.: Int. J. Mol. Med., 2, 331 (1980)

• Regioselective 1-O-deacylation can be effected with ammonia in acetonitrile at ambient temperature: Synthesis, 1121 (1985).

References

Bioactivity

PubChem BioAssay