Cas no 33228-65-8 (Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-)

Benzoic acid, 4-(β-D-glucopyranosyloxy)-3,5-dimethoxy-, is a glycosylated derivative of benzoic acid featuring a β-D-glucopyranosyl moiety attached to the aromatic ring. This compound combines the structural characteristics of benzoic acid with the solubility-enhancing properties of the glucose unit, making it particularly useful in applications requiring improved hydrophilicity. The presence of methoxy groups at the 3- and 5-positions further influences its reactivity and stability. This derivative is of interest in pharmaceutical and biochemical research, where its glycosidic linkage may enhance bioavailability or serve as a prodrug intermediate. Its well-defined structure also makes it a valuable reference standard in analytical chemistry.
Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- structure
33228-65-8 structure
Product Name:Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-
CAS No:33228-65-8
MF:C15H20O10
MW:360.313305854797
CID:308408
PubChem ID:10383888
Update Time:2025-11-02

Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-
    • Glucosyringic acid
    • 3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
    • [ "" ]
    • CHEMBL5082798
    • AKOS030573575
    • 4-(beta-d-glucopyranosyloxy)-3,5-dimethoxybenzoic acid
    • FS-9763
    • SCHEMBL19806792
    • Syringic acid-4--D-glucopyranoside
    • Gluco-syringic acid
    • EX-A4054
    • Syringic acid 4--glucopyranoside; Syringic acid glucoside
    • DTXSID20186870
    • Benzoic acid, 4-(beta-D-glucopyranosyloxy)-3,5-dimethoxy-
    • Glucosyringicacid
    • 33228-65-8
    • Syringin 4-O-beta-glucoside
    • DA-73777
    • 3,5-dimethoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxybenzoic acid
    • G89291
    • Glucosyringate
    • 3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
    • DTXCID60109361
    • Inchi: 1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)/t9-,10-,11+,12-,15+/m1/s1
    • InChI Key: BLKMDORKRDACEI-OVKLUEDNSA-N
    • SMILES: O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)OC1C(=CC(C(=O)O)=CC=1OC)OC

Computed Properties

  • Exact Mass: 360.10600
  • Monoisotopic Mass: 360.10564683g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 6
  • Complexity: 432
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1
  • Topological Polar Surface Area: 155?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.5±0.1 g/cm3
  • Boiling Point: 611.1±55.0 °C at 760 mmHg
  • Flash Point: 224.7±25.0 °C
  • PSA: 155.14000
  • LogP: -1.41930
  • Vapor Pressure: 0.0±1.8 mmHg at 25°C

Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- Security Information

Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- Pricemore >>

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Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- Production Method

Additional information on Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-

Exploring Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- (CAS No. 33228-65-8): Properties, Applications, and Market Insights

Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- (CAS No. 33228-65-8) is a naturally occurring glycosylated derivative of benzoic acid, widely studied for its unique chemical properties and potential applications in pharmaceuticals, cosmetics, and food industries. This compound, characterized by the presence of a β-D-glucopyranosyl moiety attached to a dimethoxy-substituted benzoic acid, has garnered significant attention due to its bioactive potential and structural complexity.

The molecular structure of Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- combines the aromatic properties of benzoic acid with the hydrophilic nature of glucose, making it an interesting subject for research in drug delivery systems. Recent studies highlight its potential as a natural preservative and antioxidant, aligning with the growing consumer demand for clean-label ingredients in food and personal care products.

From a chemical perspective, the presence of both glucopyranosyl and methoxy groups in this compound contributes to its solubility profile and stability. The CAS 33228-65-8 compound exhibits moderate water solubility due to the glycosidic bond, while the aromatic ring structure provides thermal stability, making it suitable for various industrial applications. Researchers are particularly interested in its structure-activity relationship, especially in relation to its potential biological effects.

In the pharmaceutical sector, Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- has shown promise in preliminary studies for its bioavailability enhancement properties. The glucose moiety may improve the absorption of certain active compounds, addressing one of the key challenges in drug development. This aligns with current trends in precision medicine and targeted drug delivery, topics frequently searched in scientific databases and AI platforms.

The cosmetic industry has shown growing interest in this compound due to its potential as a natural alternative to synthetic preservatives. With increasing consumer awareness about clean beauty and green chemistry, the demand for naturally derived ingredients like CAS 33228-65-8 has surged. Formulators are exploring its use in skincare products for its possible antioxidant and anti-aging properties.

Market analysis indicates that the global demand for specialized benzoic acid derivatives, including Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-, is expected to grow steadily in the coming years. This growth is driven by the expanding nutraceutical sector and increasing research into plant-derived bioactive compounds. The compound's potential applications in functional foods and dietary supplements make it particularly relevant to current health and wellness trends.

From a regulatory standpoint, CAS 33228-65-8 is generally recognized as safe for various applications, though specific usage guidelines may vary by region and application. Manufacturers and researchers should consult current regulations when considering this compound for commercial products. The safety profile of this glucosylated benzoic acid derivative makes it attractive compared to some synthetic alternatives.

Recent advancements in extraction and synthesis methods have improved the commercial viability of Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy-. Modern biotechnological approaches, including enzymatic synthesis and fermentation technologies, are being explored to produce this compound more efficiently. These developments respond to the increasing need for sustainable production methods in the chemical industry.

In research settings, this compound serves as an important chemical reference standard and intermediate for various synthetic pathways. Its unique structure makes it valuable for studying glycosylation reactions and aromatic compound metabolism. These research applications contribute to its importance in academic and industrial laboratories worldwide.

The future prospects for Benzoic acid, 4-(b-D-glucopyranosyloxy)-3,5-dimethoxy- appear promising, with ongoing research exploring its potential in nutraceuticals, cosmeceuticals, and pharmaceutical formulations. As consumer preferences continue to shift toward natural and sustainable ingredients, this compound is well-positioned to meet market demands. Its versatility and relatively safe profile make it a compound worth watching in the evolving landscape of specialty chemicals.

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