Sclareolide

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  Y
3D model (JSmol)	Interactive image
ChemSpider	809894  N
ECHA InfoCard	100.008.427
EC Number	209-269-0
PubChem CID	929262
UNII	37W4O0O6E6  Y
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 N Key: IMKJGXCIJJXALX-SHUKQUCYSA-N 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
Density	0.55–0.65 g/cm3
Melting point	123 °C (253 °F; 396 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) 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 ^[4] 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.