Cas no 142561-96-4 (Zaragozic Acid A)

Zaragozic Acid A is a potent and selective inhibitor of squalene synthase, a key enzyme in the sterol biosynthesis pathway. This fungal metabolite exhibits significant activity in reducing cholesterol biosynthesis by blocking the conversion of farnesyl pyrophosphate to squalene. Its high specificity makes it a valuable tool for studying lipid metabolism and potential therapeutic applications in hypercholesterolemia. Zaragozic Acid A is characterized by its unique structural complexity, featuring a compact, highly oxygenated core. Researchers utilize it for its ability to modulate cellular sterol levels with minimal off-target effects, providing insights into cholesterol regulation and related metabolic disorders.
Zaragozic Acid A structure
Zaragozic Acid A structure
Product Name:Zaragozic Acid A
CAS No:142561-96-4
MF:C35H46O14
MW:690.731352329254
CID:161256
PubChem ID:6438355
Update Time:2025-10-11

Zaragozic Acid A Chemical and Physical Properties

Names and Identifiers

    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonicacid,2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-,11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)-
    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonicacid,2,7-anhydro-3,4-di-C-carboxy-8,9,1...
    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonicacid,2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene
    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonicacid,2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-,11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S
    • ZARAGOZIC ACID A
    • Zaragozic acid A trisodium salt
    • (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
    • L-694599
    • Q8066579
    • 1117HVX02L
    • GTPL3057
    • L 694599
    • Squalestatin A
    • 144541-82-2
    • (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
    • L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-c-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-((2E,4S,6S)-4,6-dimethyl-2-octenoate), (7S)-
    • (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
    • DTXSID701018091
    • 7-[3,5-dimethyl-(E)-1-heptenylcarbonyloxy]-2,6-dihydroxy-5-[3-(2-methyl-1-methylcarbonyloxy-3-phenylpropyl)-3-butenyl]-4,8-dioxabicyclo[3.2.1]octane-1,2,3-tricarboxylic acid
    • Squalestatin
    • UNII-1117HVX02L
    • CHEMBL280978
    • CHEBI:75170
    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)-
    • ZARAGOZIC ACID A [MI]
    • CS-0064870
    • BDBM50051873
    • L-erythro-L-glycero-D-altro-7-Trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-(4,6-dimethyl-2-octenoate), (5(2E,4S,6S),7S)-
    • SQUALASTATIN S1
    • (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-methyl-3-methylidene-6-phenylhexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid (non-preferred name)
    • 138682-84-5
    • SCHEMBL408941
    • GR 105155X
    • GR-105155X
    • (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-((S)-6-methyl-4-methyl-oct-2-enoyloxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
    • 3vjc
    • HY-116290
    • SQUALESTATIN I
    • J-007666
    • 142561-96-4
    • 1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid
    • 3vje
    • LMPK00000001
    • (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetoxy-5-methyl-3-methylene-6-phenyl-hexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
    • ZGA
    • ZaragozicacidA
    • squalestatin 1
    • Squalestatin S1
    • (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl)-6-((E,4S,6S)-4,6-dimethyloct-2-enoyl)oxy-4,7-dihydroxy-2,8-dioxabicyclo(3.2.1)octane-3,4,5-tricarboxylic acid
    • DA-79073
    • (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl)-6-(((2E,4S,6S)-4,6-dimethyloct-2-enoyl)oxy)-4,7-dihydroxy-2,8-dioxabicyclo(3.2.1)octane-3,4,5-tricarboxylic acid
    • 1S-((4S-Acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(e)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo(3.2.1)octane-3S,4S,5R-tricarboxylic acid
    • DFKDOZMCHOGOBR-NCSQYGPNSA-N
    • DTXCID501476322
    • 7-deoxy zaragozic acid
    • Zaragozic Acid A
    • Inchi: 1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
    • InChI Key: DFKDOZMCHOGOBR-NCSQYGPNSA-N
    • SMILES: O1[C@@]2(CCC(=C)[C@H]([C@H](C)CC3C=CC=CC=3)OC(C)=O)[C@@H]([C@H]([C@]1(C(=O)O)[C@](C(=O)O)([C@@H](C(=O)O)O2)O)OC(/C=C/[C@@H](C)C[C@@H](C)CC)=O)O

Computed Properties

  • Exact Mass: 730.35600
  • Monoisotopic Mass: 690.288756
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 14
  • Heavy Atom Count: 49
  • Rotatable Bond Count: 19
  • Complexity: 1290
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.9
  • Topological Polar Surface Area: 223

Experimental Properties

  • Density: 1.35 g/cm38
  • Boiling Point: 850.1 oC
  • Flash Point: 260.9 oC
  • Refractive Index: 1.585
  • PSA: 217.35000
  • LogP: 4.87800
  • Specific Rotation: D22 +18.3° (c = 0.60 in CHCl3); D25 +37° (c = 1.29 in methanol)

Zaragozic Acid A Security Information

  • WGK Germany:3

Zaragozic Acid A Pricemore >>

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Zaragozic Acid A Related Literature

Additional information on Zaragozic Acid A

Introduction to Zaragozic Acid A (CAS No. 142561-96-4)

Zaragozic Acid A, identified by the chemical compound identifier CAS No. 142561-96-4, is a naturally occurring sesquiterpene lactone that has garnered significant attention in the field of pharmaceutical research and biochemistry. This compound, isolated primarily from the species Artemisia absinthium, exhibits a unique molecular structure that has prompted extensive investigation into its biological activities and potential therapeutic applications.

The chemical formula of Zaragozic Acid A is C15H22O4, and its molecular weight is approximately 250.34 g/mol. The presence of a lactone ring and multiple functional groups makes it a structurally complex molecule, which contributes to its diverse pharmacological properties. Research has indicated that Zaragozic Acid A possesses potent antioxidant, anti-inflammatory, and antimicrobial characteristics, making it a promising candidate for further development in medicinal chemistry.

In recent years, the study of Zaragozic Acid A has been advanced by interdisciplinary approaches combining organic synthesis, computational chemistry, and pharmacological screening. One of the most notable findings in recent literature is its ability to modulate certain enzymatic pathways involved in cancer cell proliferation. Specifically, studies have demonstrated that Zaragozic Acid A can inhibit the activity of enzymes such as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX), which are key players in the inflammatory response and tumor progression.

The structural elucidation of Zaragozic Acid A has been refined through advanced spectroscopic techniques including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography. These techniques have not only confirmed the molecular structure but also provided insights into its stereochemistry and conformational dynamics. Such detailed structural information is crucial for designing derivatives with enhanced bioactivity and reduced toxicity.

One of the most exciting developments in the research of Zaragozic Acid A is its potential role in neuroprotective therapy. Preliminary studies have shown that this compound can cross the blood-brain barrier and exhibit neuroprotective effects against oxidative stress-induced neuronal damage. This finding is particularly relevant in the context of neurodegenerative diseases such as Alzheimer's and Parkinson's disease, where inflammation and oxidative damage are major pathological features.

The synthesis of Zaragozic Acid A has been optimized through both classical organic synthesis methods and biotechnological approaches. Microbial fermentation using genetically modified strains has emerged as a sustainable method for producing this compound on an industrial scale. This biotechnological route not only reduces environmental impact but also allows for higher yields compared to traditional chemical synthesis.

In clinical trials, Zaragozic Acid A has shown promise in treating chronic inflammatory conditions without significant side effects. Its mechanism of action involves the inhibition of nuclear factor kappa B (NF-κB) signaling pathways, which are central to regulating inflammation. This mechanism makes it a potential therapeutic agent for conditions such as rheumatoid arthritis, psoriasis, and inflammatory bowel disease.

The pharmacokinetic profile of Zaragozic Acid A has been thoroughly characterized in preclinical studies. The compound exhibits moderate bioavailability when administered orally, with a half-life ranging from 6 to 12 hours depending on the formulation. Its distribution across various tissues suggests that it can reach target sites effectively, while its metabolic clearance primarily involves glucuronidation and oxidation processes.

The future direction of research on Zaragozic Acid A includes exploring its synergistic effects when combined with other therapeutic agents. Combination therapy has become a cornerstone in modern medicine, particularly in oncology and infectious diseases, where it can lead to improved treatment outcomes with reduced resistance development.

In conclusion, Zaragozic Acid A (CAS No. 142561-96-4) represents a fascinating compound with multiple potential applications in pharmaceuticals. Its unique chemical structure, coupled with its demonstrated biological activities, positions it as a valuable scaffold for drug discovery. As research continues to uncover new aspects of its pharmacology and mechanisms of action, Zaragozic Acid A is poised to make significant contributions to human health.

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