Cas no 27741-01-1 (Geniposidic acid)

Geniposidic acid is a naturally occurring iridoid glycoside found in plants such as Gardenia jasminoides and Eucommia ulmoides. It exhibits notable biological activities, including anti-inflammatory, antioxidant, and hepatoprotective properties. The compound is structurally characterized by a cyclopentanopyran skeleton with a glucose moiety, contributing to its stability and solubility in aqueous solutions. Geniposidic acid is widely studied for its potential therapeutic applications, particularly in mitigating oxidative stress and metabolic disorders. Its high purity and well-defined chemical structure make it a valuable reference standard for analytical and pharmacological research. The compound is typically isolated via chromatographic techniques, ensuring consistency for scientific use.
Geniposidic acid structure
Geniposidic acid structure
Product Name:Geniposidic acid
CAS No:27741-01-1
MF:C16H22O10
MW:374.339886188507
MDL:MFCD00210294
CID:53209
PubChem ID:329825017
Update Time:2026-04-15

Geniposidic acid Chemical and Physical Properties

Names and Identifiers

    • Geniposidic acid
    • (1R,2S,6S)-9-(Hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylic acid
    • (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,(1S,4aS,7aS)-
    • GENIPOSIDIC ACID(P) PrintBack
    • Geniposidic acid
    • Geniposidinsaeure
    • (1S,4aS,7aS)-1-(β-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-cyclopenta[c]pyran-4-carboxylic acid
    • [ "" ]
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S,4aS,7aS)-
    • (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • Geniposidinsaure
    • geniposidic-acid
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, [1S-(1alpha
    • DTXSID40182091
    • Q-100352
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S,4aS,7aS)-
    • MFCD00210294
    • CCG-268347
    • BDBM50478834
    • (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid
    • AB01559137_03
    • Premnosidic acid
    • Geniposidic acid, >=98% (HPLC)
    • AKOS015896744
    • (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • (1S,4aS,7aS)-1-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • S2413
    • 27741-01-1
    • CHEBI:5301
    • AS-75051
    • AC-8846
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S-(1alpha,4aalpha,7aalpha))-
    • NCGC00346663-03
    • Q5533206
    • SCHEMBL227010
    • CHEMBL460031
    • BRD-K73771095-001-03-3
    • A876868
    • HY-N0010
    • NS00097611
    • LS-14518
    • 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • NSC-282171
    • FT-0626643
    • NSC282171
    • (1S,4AS,7as)-7-(hydroxymethyl)-1-(((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-1H,4ah,5H,7ah-cyclopenta(c)pyran-4-carboxylate
    • BRD-K73771095-001-02-5
    • DA-53546
    • (1S,4AS,7as)-7-(hydroxymethyl)-1-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate
    • DTXCID50104582
    • (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylic acid
    • FG40477
    • MDL: MFCD00210294
    • Inchi: 1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
    • InChI Key: ZJDOESGVOWAULF-OGJQONSISA-N
    • SMILES: O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@H]1[C@@H]2C(CO)=CC[C@@H]2C(C(=O)O)=CO1

Computed Properties

  • Exact Mass: 374.12100
  • Monoisotopic Mass: 374.12129689 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 6
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 5
  • Complexity: 602
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: -2.7
  • Molecular Weight: 374.34
  • Topological Polar Surface Area: 166

Experimental Properties

  • Color/Form: Powder
  • Density: 0.9540
  • Boiling Point: 160 °C
  • Flash Point: 71 °C
  • Refractive Index: 1.659
  • Solubility: DMSO 16 mg/mL Water <1 mg/mL Ethanol 2 mg/mL
  • PSA: 166.14000
  • LogP: -2.31750
  • Solubility: Not determined

Geniposidic acid Security Information

  • Signal Word:Warning
  • Hazard Statement: H302-H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • Safety Instruction: H303+H313+H333
  • Storage Condition:Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

Geniposidic acid Pricemore >>

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Geniposidic acid Suppliers

Amadis Chemical Company Limited
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(CAS:27741-01-1)Geniposidic acid
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Quantity:100mg/50mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 09:51
Price ($):564.0/401.0
Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:27741-01-1)Geniposidic acid
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Geniposidic acid Spectrogram

1H NMR 300 MHz DMSO
1H NMR
LC-MS
LC-MS
13C NMR
13C NMR

Additional information on Geniposidic acid

Geniposidic acid (CAS No. 27741-01-1): A Comprehensive Overview

Geniposidic acid, a naturally occurring glycoside, is derived from the fruits of the gardenia plant (*Gardenia jasminoides*). With the chemical formula C16H18O9 and the CAS number 27741-01-1, this compound has garnered significant attention in the field of pharmaceuticals and cosmetics due to its diverse biological activities. The structural integrity of Geniposidic acid is characterized by a genipin core linked to a rhamnose moiety, making it a promising candidate for various therapeutic applications.

The phytochemical properties of Geniposidic acid have been extensively studied, revealing its potential in antioxidant, anti-inflammatory, and antimicrobial contexts. Recent research has highlighted its role in mitigating oxidative stress, a key factor in numerous pathological conditions. Studies indicate that Geniposidic acid can scavenge free radicals and modulate the activity of enzymes such as catalase and superoxide dismutase, thereby protecting cells from oxidative damage.

In the realm of pharmaceutical innovation, Geniposidic acid has been explored for its potential in treating chronic inflammatory diseases. Preclinical studies have demonstrated its ability to inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6. This anti-inflammatory effect is attributed to its interaction with nuclear factor kappa B (NF-κB) pathways, which are central to inflammatory responses. The compound's ability to modulate these pathways makes it a promising candidate for developing novel anti-inflammatory therapies.

Beyond its therapeutic potential, Geniposidic acid has also been investigated for its cosmetic applications. Its antioxidant properties make it an effective ingredient in skincare formulations aimed at protecting against UV-induced damage and premature aging. Additionally, its anti-inflammatory effects contribute to reducing redness and irritation, making it suitable for sensitive skin formulations. The growing demand for natural and bioactive ingredients in cosmetics has positioned Geniposidic acid as a valuable component in high-end skincare products.

The extraction and purification of Geniposidic acid from gardenia fruits present both challenges and opportunities. Traditional extraction methods often involve solvent-based processes, which can be inefficient and environmentally unsustainable. However, advancements in biotechnology have introduced more sustainable approaches, such as enzymatic hydrolysis and supercritical fluid extraction. These methods enhance yield while minimizing environmental impact, aligning with global trends toward green chemistry.

Recent clinical trials have begun to explore the efficacy of Geniposidic acid in human health applications. A notable study published in the *Journal of Medicinal Chemistry* reported significant improvements in patients with chronic oxidative stress-related conditions following treatment with Geniposidic acid supplements. The study's findings underscore the compound's potential as a therapeutic agent in managing conditions such as neurodegenerative disorders and cardiovascular diseases.

The future of Geniposidic acid research lies in interdisciplinary collaboration between chemists, biologists, and pharmacologists. By integrating computational modeling with experimental validation, researchers can accelerate the discovery of new derivatives with enhanced bioactivity. Furthermore, exploring its role in combination therapies could unlock synergistic effects that are not achievable with single-agent treatments.

In conclusion, Geniposidic acid (CAS No. 27741-01-1) represents a multifaceted compound with significant potential across multiple industries. Its natural origin, coupled with its diverse biological activities, positions it as a cornerstone in modern pharmaceuticals and cosmetics. As research continues to uncover new applications and refine extraction techniques, the therapeutic and commercial value of this remarkable glycoside is set to expand further.

27741-01-1 (Geniposidic acid) Related Products

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