Sclareolide

Sclareolide
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	809894 ;
ECHA InfoCard	100.008.427
EC Number	209-269-0;
PubChem CID	929262;
UNII	37W4O0O6E6 ;
CompTox Dashboard (EPA)	DTXSID8047686 ;
	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/s1 Key: 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/s1 Key: IMKJGXCIJJXALX-SHUKQUCYBO;
	SMILES C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC(=O)O3)C)(C)C;
Properties
Chemical formula	C16H26O2
Molar mass	250.382 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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.

References

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.
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.
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.

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[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.

[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.