Cas no 28199-69-1 ((2S,3R)-Dihydrodehydroconiferyl Alcohol)

(2S,3R)-Dihydrodehydroconiferyl Alcohol is a chiral lignan derivative with notable applications in organic synthesis and pharmaceutical research. Its stereospecific (2S,3R) configuration enhances its utility as a building block for complex molecules, particularly in the development of bioactive compounds. The compound’s rigid structure and functional groups, including hydroxyl and aromatic moieties, facilitate selective modifications, making it valuable for asymmetric synthesis. Its natural origin also positions it as an intermediate in the study of plant-derived metabolites. High purity and well-defined stereochemistry ensure reproducibility in research applications. This compound is particularly relevant in investigations of lignan biosynthesis and potential pharmacological activities.
(2S,3R)-Dihydrodehydroconiferyl Alcohol structure
28199-69-1 structure
Product Name:(2S,3R)-Dihydrodehydroconiferyl Alcohol
CAS No:28199-69-1
MF:C20H24O6
MW:360.400966644287
CID:837582
PubChem ID:384679
Update Time:2025-05-19

(2S,3R)-Dihydrodehydroconiferyl Alcohol Chemical and Physical Properties

Names and Identifiers

    • Dihydrodehydrodiconiferyl-alcohol
    • 5-Benzofuranpropanol, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-, (2R,3S)-
    • 4-[(2S,3R)-3-(Hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-di hydro-1-benzofuran-2-yl]-2-methoxyphenol
    • DIHYDRODEHYDRODICONIFERYL ALCOHOL
    • (+)-(7S,8R)-dihy
    • (6,7-diethoxy-3-methyl-1-benzofuran-2-yl)(morpholin-4-yl)methanone
    • (7S,8R)-dihydrodehydrodiconiferyl alcohol
    • 3,5'-dimethoxy-4',7-epoxy-8,3'-neolignane-4,9,9'-triol
    • 3'-methylcedrusin
    • 4-((6,7-Diethoxy-3-methyl-2-benzofuranyl)carbonyl)morpholine
    • AC1L54S6
    • AC1Q5G30
    • Betulinsaeure
    • BRN 1158591
    • CTK4I3613
    • KST-1A5484
    • Morpholine, 4-((6,7-diethoxy-3-methyl-2-benzofuranyl)carbonyl)-
    • (2S,3R)-Dihydrodehydroconiferyl alcohol
    • Dehydroconiferyl alcohol
    • FS-9708
    • XD172959
    • 28199-69-1
    • (2S,3R)-dihydrodehydrodiconiferyl alcohol
    • DTXSID501272203
    • CHEBI:143257
    • AKOS040761622
    • (+)-Dihydrodehyrodiconiferyl Alcohol
    • CS-0103769
    • NSC674906
    • 5-Benzofuranpropanol,2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-, (2S-trans)-
    • CHEMBL261907
    • SBLZVJIHPWRSQQ-HNAYVOBHSA-
    • 4-[(2S, 3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2, 3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
    • InChI=1/C20H24O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h5-6,8-10,15,19,21-23H,3-4,7,11H2,1-2H3/t15-,19+/m0/s1
    • HY-129144
    • NSC-674906
    • dihydrodehydrodiconifery alcohol
    • 4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
    • NCI60_026519
    • 4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2-methoxy-phenol
    • NCGC00385401-01
    • SCHEMBL4545346
    • 3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-1-ol
    • Di-hydrodehydrodiconiferyl alcohol
    • (+)-Dihydrodehydrodiconiferyl alcohol
    • (2S,3R)-Dihydrodehydroconiferyl Alcohol
    • Inchi: 1S/C20H24O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h5-6,8-10,15,19,21-23H,3-4,7,11H2,1-2H3/t15-,19+/m0/s1
    • InChI Key: SBLZVJIHPWRSQQ-HNAYVOBHSA-N
    • SMILES: O1C2C(=CC(CCCO)=CC=2[C@H](CO)[C@H]1C1C=CC(=C(C=1)OC)O)OC

Computed Properties

  • Exact Mass: 360.157
  • Monoisotopic Mass: 360.157
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 7
  • Complexity: 433
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 88.4A^2
  • XLogP3: 2.1

Experimental Properties

  • Color/Form: Powder
  • Density: 1.261
  • Boiling Point: 540.9 °C at 760 mmHg
  • Flash Point: 280.9 °C
  • PSA: 88.38000
  • LogP: 2.54390

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Additional information on (2S,3R)-Dihydrodehydroconiferyl Alcohol

Recent Advances in the Study of (2S,3R)-Dihydrodehydroconiferyl Alcohol (CAS: 28199-69-1): A Promising Bioactive Compound

(2S,3R)-Dihydrodehydroconiferyl Alcohol (CAS: 28199-69-1) is a naturally occurring lignan derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its diverse biological activities. Recent studies have highlighted its potential as an anti-inflammatory, antioxidant, and neuroprotective agent, making it a promising candidate for therapeutic development. This research briefing synthesizes the latest findings on this compound, focusing on its chemical properties, mechanisms of action, and potential applications in medicine.

One of the key breakthroughs in recent research is the elucidation of the compound's mechanism of action in modulating inflammatory pathways. A 2023 study published in the Journal of Natural Products demonstrated that (2S,3R)-Dihydrodehydroconiferyl Alcohol significantly inhibits the production of pro-inflammatory cytokines such as TNF-α and IL-6 in macrophage cells. The study employed a combination of molecular docking simulations and in vitro assays to identify the compound's interaction with key proteins in the NF-κB signaling pathway, providing a molecular basis for its anti-inflammatory effects.

In addition to its anti-inflammatory properties, recent investigations have explored the compound's potential in neurodegenerative diseases. Research published in Neurochemistry International (2024) revealed that (2S,3R)-Dihydrodehydroconiferyl Alcohol exhibits neuroprotective effects in models of Parkinson's disease by reducing oxidative stress and preventing dopaminergic neuron loss. The study utilized both cell culture and animal models, demonstrating dose-dependent protection against neurotoxicity induced by 6-hydroxydopamine, a commonly used Parkinson's disease model.

The compound's antioxidant capacity has also been a focus of recent research. A 2024 study in Free Radical Biology and Medicine employed advanced spectroscopic techniques to characterize the radical scavenging activity of (2S,3R)-Dihydrodehydroconiferyl Alcohol. The results showed superior antioxidant activity compared to standard antioxidants like vitamin E, particularly in lipid peroxidation systems. This finding suggests potential applications in preventing oxidative stress-related conditions, including cardiovascular diseases and aging.

From a chemical perspective, recent advances in synthetic methodologies have improved access to this compound. A 2023 publication in Organic Letters described an efficient asymmetric synthesis route for (2S,3R)-Dihydrodehydroconiferyl Alcohol with high enantiomeric purity. This development is particularly significant as it addresses previous challenges in obtaining sufficient quantities of the compound for detailed biological studies and potential clinical applications.

Looking forward, several research groups are investigating the pharmacokinetic properties and potential structural modifications of (2S,3R)-Dihydrodehydroconiferyl Alcohol to enhance its bioavailability and therapeutic efficacy. Preliminary results from animal studies suggest reasonable oral bioavailability, though further optimization may be required for clinical translation. The compound's multi-target activity profile presents both opportunities and challenges for drug development, requiring careful consideration of structure-activity relationships.

In conclusion, recent research on (2S,3R)-Dihydrodehydroconiferyl Alcohol (CAS: 28199-69-1) has significantly advanced our understanding of its therapeutic potential. The compound's diverse biological activities, coupled with improved synthetic accessibility, position it as a promising lead compound for the development of novel treatments for inflammatory, neurodegenerative, and oxidative stress-related disorders. Future research directions should focus on detailed mechanistic studies, preclinical evaluation of efficacy and safety, and exploration of potential synergistic effects with existing therapies.

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