Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Constructing conformationally constrained macrobicyclic musks.

P Kraft1, R Cadalbert

  • 1Givaudan Dübendorf Ltd., Fragrance Research, Switzerland. philip.kraft@givaudan.com

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 4, 2001
PubMed
Summary

Researchers explored structure-odor relationships in musks by synthesizing novel macrobicyclic compounds. Compound 22 exhibited the strongest musk odor, providing insights into musk receptor interactions.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Association of gene variant type and location with breast cancer risk in the general population.

Annals of oncology : official journal of the European Society for Medical Oncology·2025
Same author

The age-dependent association of risk factors with pancreatic cancer.

Annals of oncology : official journal of the European Society for Medical Oncology·2022
Same author

Detection of hidden model errors by combining single and multi-criteria calibration.

The Science of the total environment·2021
Same author

Inhibition of prostaglandin-degrading enzyme 15-PGDH rejuvenates aged muscle mass and strength.

Science (New York, N.Y.)·2020
Same author

Relationship between body mass index and atopic dermatitis: a Mendelian randomization approach in exploring causality: a critical appraisal.

The British journal of dermatology·2020
Same author

Using a Mendelian randomization approach to explore a causal relationship between vitamin D and nonmelanoma skin cancer.

The British journal of dermatology·2018

Area of Science:

  • Organic Chemistry
  • Olfactory Science
  • Computational Chemistry

Background:

  • Musk compounds are crucial in perfumery.
  • Understanding the structure-odor relationship of musks is key to designing new fragrance molecules.
  • Macrocyclic and polycyclic musks have distinct structural features influencing their scent profiles.

Purpose of the Study:

  • To investigate the structure-odor correlation of macrocyclic musks.
  • To synthesize conformationally constrained analogues of known musks to probe receptor interactions.
  • To elucidate the role of specific structural features, like methyl groups, in musk odor perception.

Main Methods:

  • Synthesis of novel [7.5.1]- and [8.4.1]-macrobicyclic compounds.
  • Utilized catalytic hydrogenation, alpha-alkylation, acid-catalyzed cyclization, oxidative cleavage, and tosylhydrazone reduction.

Related Experiment Videos

  • Conformational analysis and superposition studies with known musk odorants like Galaxolide.

    • Main Results:

    • Compound (1R,6R,9R)-(+)-6-methyl-4-oxa-bicyclo[7.5.1]pentadecan-3-one (22) displayed the most potent musk odor.
    • Stereoisomers (23) and related macrobicycles (18) with methyl groups hindering receptor interaction showed reduced or faint odors.
    • Demethyl analogues (7 and 12) exhibited only very faint odors, highlighting the importance of the methyl group.

    Conclusions:

    • The specific stereochemistry and presence of a methyl group at the C-6 position are critical for potent musk odor.
    • Conformational restriction plays a significant role in the interaction with musk receptors.
    • This study provides valuable structure-activity relationship data for the design of novel musk compounds.