Sclareolide

Sclareolide
IUPAC name

3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[8,7-d]furan-2-one
Other names

Norambreinolide
Identifiers
CAS number 564-20-5 Y
PubChem 61129
UNII 37W4O0O6E6 Y
Jmol-3D images Image 1
Properties
Molecular formula C16H26O2
Molar mass 250.38 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sclareolide is a sesquiterpene lactone natural product derived from various plant sources including Salvia sclarea, Salvia yosgadensis,[1] and cigar tobacco.[2] It is a close analog of sclareol, a plant antifungal compound.[3]

It is used as a fragrance in cosmetics and has been more recently marketed as a weight loss supplement, though there is no clinical evidence to support this effect.

The company WILD believes and presumably tries to use sclareolide to hypothetically block the perception of "off" flavors in potassium chloride when used as a table salt substitute.[4]

References

  1. ^ Topcu, Guelacti; Ulubelen, Ayhan; Tam, Timothy Chit-Ming; Che, Chun-Tao (1996). "Norditerpenes and Norsesterterpenes from Salvia yosgadensis". Journal of Natural Products 59 (2): 113–116. doi:10.1021/np960028h. 
  2. ^ Kaneko, Hajime (1971). "Aroma of cigar tobacco. II. Isolation of norambreinolide from cigar tobacco". Agricultural and Biological Chemistry 35 (9): 1461–1462. 
  3. ^ Jasiński M, Stukkens Y, Degand H, Purnelle B, Marchand-Brynaert J, Boutry M (2001). "A Plant Plasma Membrane ATP Binding Cassette–Type Transporter Is Involved in Antifungal Terpenoid Secretion". Plant Cell 13 (5): 1095–107. doi:10.1105/tpc.13.5.1095. PMC 135550. PMID 11340184. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=135550. 
  4. ^ http://www.wildflavors.com/index.cfm?fuseaction=news.item&newsCategoryID=B57723F5-CF1C-2465-18BFD630DB5F7B15&newsItemID=F75F69F9-AF3A-F845-BB676985C8D284E2