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New macrocyclic musk compounds.

Hiroyuki Matsuda1, Shinya Watanabe, Kenichi Yamamoto

  • 1Takasago International Corporation, Central Research Laboratory, 1-4-11 Nishi-yawata, Hiratsuka city, Kanagawa 254-0073, Japan. hiroyuki_matsuda@takasago.com

Chemistry & Biodiversity
|December 29, 2006
PubMed
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New macrocyclic compounds with a 1,6-dioxa structure exhibit musk odors, similar to traditional musks. The most intense and pleasant musk character was observed in 16-membered rings, regardless of saturation.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Olfactory Science

Background:

  • Macrocyclic ketones and lactones are well-known for their musk fragrance.
  • The development of novel musk compounds is of interest in the fragrance industry.

Purpose of the Study:

  • To synthesize and evaluate the olfactory properties of new macrocyclic compounds.
  • To explore the potential of 1,6-dioxa macrocycles and optically active 3-methyl macrolides as musk ingredients.

Main Methods:

  • Synthesis of macrocycles using intramolecular metathesis catalyzed by the Grubbs catalyst.
  • Olfactory evaluation of synthesized unsaturated and saturated 1,6-dioxa compounds and optically active 3-methyl macrolides.

Main Results:

Related Experiment Videos

  • Eight new 1,6-dioxa macrocycles (unsaturated and saturated) were synthesized and found to possess musk odors.
  • Sixteen-membered 1,6-dioxa macrocycles exhibited intense and pleasant musk characteristics.
  • Optically active 3-methyl macrolides showed musk notes, with (R)-configured 15- and 16-membered rings being particularly pleasant.

    • Conclusions:

    • 1,6-dioxa macrocycles can serve as effective musk compounds, even without a carbonyl group.
    • Ring size and stereochemistry are critical factors influencing the intensity and quality of musk fragrance in macrocyclic compounds.