Cas no 22149-28-6 (16-Hydroxytabersonine)

16-Hydroxytabersonine is a monoterpenoid indole alkaloid derived from the tabersonine framework, featuring a hydroxyl group at the C-16 position. This structural modification enhances its reactivity and potential as a key intermediate in the synthesis of complex natural products and pharmaceuticals. Its well-defined stereochemistry and functional group make it valuable for research in alkaloid chemistry, particularly in studies involving biosynthetic pathways or medicinal chemistry applications. The compound’s purity and stability under controlled conditions ensure reliable performance in experimental settings. Researchers utilize 16-Hydroxytabersonine for its role in exploring structure-activity relationships and developing novel bioactive molecules.
16-Hydroxytabersonine structure
16-Hydroxytabersonine structure
Product Name:16-Hydroxytabersonine
CAS No:22149-28-6
MF:C21H24N2O3
MW:352.426865577698
CID:239020
PubChem ID:443326
Update Time:2025-05-22

16-Hydroxytabersonine Chemical and Physical Properties

Names and Identifiers

    • Aspidospermidine-3-carboxylicacid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5a,12R,19a)-
    • 11-Hydroxytabersonine
    • Methyl (5α,12β,19α)-16-hydroxy-2,3,6,7-tetradehydroaspidospermidi ne-3-carboxylate
    • 11-hydroxyoleic acid
    • 9-Octadecenoic acid, 11-hydroxy-
    • 9-Octadecenoic acid, 11-hydroxy-, (Z)-
    • AGN-PC-0CPW4C
    • CTK3F8137
    • [ "" ]
    • 16-Hydroxytabersonine
    • W1101
    • C11643
    • Q20179989
    • HY-N1021
    • methyl (1R,12R,19S)-12-ethyl-5-hydroxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate
    • CS-0016257
    • methyl (1R, 12R, 19S)-12-ethyl-5-hydroxy-8, 16-diazapentacyclo[10.6.1.01, 9.02, 7.016, 19]nonadeca-2(7), 3, 5, 9, 13-pentaene-10-carboxylate
    • DTXSID601032123
    • AKOS032962286
    • UNII-GV2G76UPD2
    • 1H-Indolizino(8,1-cd)carbazole, aspidospermidine-3-carboxylic acid deriv.
    • ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-16-HYDROXY-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-
    • methyl 16-hydroxy-2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate
    • CHEMBL2011510
    • CHEBI:17699
    • 22149-28-6
    • GV2G76UPD2
    • Tabersonine, 11-hydroxy-
    • NSC-815331
    • SCHEMBL4131340
    • Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5alpha,12R,19alpha)-
    • FS-9603
    • NSC815331
    • NS00094508
    • Methyl 12-ethyl-5-hydroxy-8,16-diazapentacyclo(10.6.1.0,.0,.0,)nonadeca-2(7),3,5,9,13-pentaene-10-carboxylic acid
    • methyl (1R,12R,19S)-12-ethyl-5-hydroxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate
    • Methyl 12-ethyl-5-hydroxy-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylic acid
    • DA-69443
    • Inchi: 1S/C21H24N2O3/c1-3-20-7-4-9-23-10-8-21(19(20)23)15-6-5-13(24)11-16(15)22-17(21)14(12-20)18(25)26-2/h4-7,11,19,22,24H,3,8-10,12H2,1-2H3/t19-,20-,21-/m0/s1
    • InChI Key: FXUFRJQCBVSCRZ-ACRUOGEOSA-N
    • SMILES: O(C)C(C1C[C@@]2(C=CCN3CC[C@@]4(C5C=CC(=CC=5NC4=1)O)[C@@H]32)CC)=O

Computed Properties

  • Exact Mass: 352.17869263g/mol
  • Monoisotopic Mass: 352.17869263g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 3
  • Complexity: 701
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3
  • Topological Polar Surface Area: 61.8

Experimental Properties

  • Color/Form: Powder

16-Hydroxytabersonine Security Information

  • Storage Condition:Store at room temperature, 2-8 ℃ is better

16-Hydroxytabersonine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd.
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Aspidospermidine-3-carboxylicacid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5a,12R,19a)-
22149-28-6
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Additional information on 16-Hydroxytabersonine

Recent Advances in the Study of 16-Hydroxytabersonine (CAS: 22149-28-6): A Promising Compound in Chemical Biology and Medicine

In recent years, the compound 16-Hydroxytabersonine (CAS: 22149-28-6) has garnered significant attention in the field of chemical biology and medicinal research. This monoterpenoid indole alkaloid, derived from the Tabernaemontana genus, has shown promising pharmacological properties, particularly in the context of anticancer and neuroprotective activities. The renewed interest in this compound is driven by its unique structural features and its potential as a scaffold for drug development. This research brief aims to synthesize the latest findings on 16-Hydroxytabersonine, highlighting its mechanisms of action, therapeutic applications, and recent advancements in synthesis and modification.

One of the most notable breakthroughs in the study of 16-Hydroxytabersonine is its role in modulating cellular pathways associated with apoptosis and autophagy. Recent in vitro studies have demonstrated that this compound exhibits selective cytotoxicity against various cancer cell lines, including breast, lung, and glioblastoma models. Researchers have identified its ability to inhibit key signaling molecules such as PI3K/AKT and mTOR, which are critical for tumor survival and proliferation. Furthermore, 16-Hydroxytabersonine has been shown to induce oxidative stress in cancer cells, leading to DNA damage and subsequent cell death. These findings underscore its potential as a lead compound for developing novel chemotherapeutic agents.

In addition to its anticancer properties, 16-Hydroxytabersonine has also been investigated for its neuroprotective effects. A 2023 study published in the Journal of Natural Products revealed that this compound can cross the blood-brain barrier and exert protective effects against neurodegenerative conditions such as Alzheimer's and Parkinson's diseases. The study attributed these effects to the compound's ability to reduce neuroinflammation and inhibit the aggregation of amyloid-beta plaques. These results open new avenues for exploring 16-Hydroxytabersonine as a therapeutic agent for central nervous system disorders.

From a chemical synthesis perspective, recent efforts have focused on optimizing the production of 16-Hydroxytabersonine to improve yield and scalability. A team at the University of Cambridge reported a novel biocatalytic approach using engineered enzymes to facilitate the hydroxylation of tabersonine at the C-16 position. This method not only enhances the efficiency of synthesis but also reduces the reliance on traditional plant extraction methods, which are often limited by low yields and environmental concerns. Such advancements are critical for ensuring a sustainable supply of this compound for further research and clinical applications.

Despite these promising developments, challenges remain in the clinical translation of 16-Hydroxytabersonine. Issues such as bioavailability, pharmacokinetics, and potential off-target effects need to be addressed through rigorous preclinical studies. However, the growing body of evidence supporting its therapeutic potential makes it a compelling candidate for future drug development. As research continues to unravel the multifaceted properties of this compound, 16-Hydroxytabersonine is poised to play a pivotal role in the next generation of biologically active molecules in medicine.

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