4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Basic Information

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CAS Number

64291-41-4

Molecular Formula

C21H26O11

Molecular Weight

454.43 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Physical State

Powder

Boiling Point

551.4°C at 760 mmHg

SMILES

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OCC1=CC=C(O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O2)C=C1

InChI

InChI=1S/C21H26O11/c1-11(23)27-10-17-18(28-12(2)24)19(29-13(3)25)20(30-14(4)26)21(32-17)31-16-7-5-15(9-22)6-8-16/h5-8,17-22H,9-10H2,1-4H3/t17-,18-,19+,20-,21-/m1/s1

InChIKey

HGUDVDQXCUHOED-YMQHIKHWSA-N

LogP

0.6408

Topological Polar Surface Area

143.89000000000001 Å²

Hydrogen Bond Donor/Acceptor

1 / 11

Complexity

671

Synonyms & References

English

(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
b-D-Glucopyranoside,4-(hydroxymethyl)phenyl, 2,3,4,6-tetraacetate
Acegastrodine
ACETAGASTRODINE
4-Cyanobenzyl alcohol
4-hydroxymethylbenzenecarbonitrile
p-cyanobenzyl alcohol
p-hydroxymethylbenzonitrile
[(2R,3R,4S,5R,6S)-3,4,5-Triacetyloxy-6-[4-(hydroxymethyl)phenoxy]oxan-2-yl]methyl acetate
Acetagastrodin
2,3,4,6-Tetra-O-acetyl-4-(hydroxymethyl)phenyl-b-D-glucopyranoside
beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl, 2,3,4,6-tetro-O-acetate
Acegastrodin
STL507266
API0016803
AK141997
AX8112046
V0268
4-(Hydroxymethyl)phenyl-beta-Dglucopyranoside tetraacetate
b-D-G

MDL Number

MFCD01725344

FAQ

What are the physical and chemical properties of 4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (CAS: 64291-41-4)?

4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside is a white crystalline solid with a molecular weight of approximately 617.6 g/mol. It has limited water solubility but is soluble in various organic solvents. Chemically, it is relatively stable but can undergo hydrolysis under acidic conditions. Its reactivity is moderate, and it is typically used in synthetic chemistry and pharmaceutical applications.

How is 4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (CAS: 64291-41-4) typically synthesized?

4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside is typically synthesized via a multi-step process involving the acetylation of a glucopyranoside with 4-hydroxymethylphenol. This involves the use of acetic anhydride and a suitable catalyst, such as acetic acid or a Lewis acid. The reaction yields a white solid with high purity, and the process is carried out under mild conditions to ensure high selectivity and yield.

What industries use 4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (CAS: 64291-41-4)?

4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside is primarily used in the pharmaceutical and chemical industries for the synthesis of complex molecules and in research applications. It is also utilized in the production of certain materials, including polymers and sensors, due to its unique chemical structure and reactivity.

What precautions should be taken when handling 4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (CAS: 64291-41-4)?

When handling 4-(Hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside, it is essential to use personal protective equipment (PPE), including gloves and goggles, to protect against skin and eye contact. The compound should be stored in a cool, dry place away from direct sunlight and sources of heat. In case of spillage, it should be cleaned up using appropriate methods and materials, and the area should be thoroughly ventilated. Always refer to the Safety Data Sheet (SDS) for detailed handling and emergency procedures.