Misplaced Pages

Sclareolide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Sclareolide
Sclareolide
Names
IUPAC name 3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphthofuran-2-one
Other names Norambreinolide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.427 Edit this at Wikidata
EC Number
  • 209-269-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1Key: IMKJGXCIJJXALX-SHUKQUCYSA-N
  • InChI=1/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1Key: IMKJGXCIJJXALX-SHUKQUCYBO
SMILES
  • C12CCCC(1CC3(2CC(=O)O3)C)(C)C
Properties
Chemical formula C16H26O2
Molar mass 250.382 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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.

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. doi:10.1080/00021369.1971.10860098. S2CID 82467628.
  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.
  4. Api, A.M.; et al. (2022). "RIFM fragrance ingredient safety assessment, sclareolide, CAS Registry Number 564-20-5". Food and Chemical Toxicology. 167: 113379. doi:10.1016/j.fct.2022.113379. PMID 35995076. S2CID 251696291.
Categories: