Sclareol

Sclareol

Names
IUPAC name (1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Other names Labd-14-ene-8,13-diol
Identifiers
CAS Number	515-03-7
ChEBI	CHEBI:9053
ChemSpider	143282
Jmol interactive 3D	Image
KEGG	C09183
PubChem	163263
InChI InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1 Key: XVULBTBTFGYVRC-HHUCQEJWSA-N InChI=1/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1 Key: XVULBTBTFGYVRC-HHUCQEJWBX
SMILES CC1(C)CCC[C@@]2(C)[C@@]1([H])CC[C@@](C)(O)[C@@H]2CC[C@](O)(C)C=C
Properties
Chemical formula	C20H36O2
Molar mass	308.51 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

Sclareol is a fragrant chemical compound found in clary sage (Salvia sclarea), from which it derives its name. It is classified as a bicyclic diterpene alcohol. It is an amber colored solid with a sweet, balsamic scent.^[1]

Sclareol is used as a fragrance in cosmetics and perfumes and as flavoring in food. Sclareol and other similar substances may be prepared from sclareolide.

Sclareol is also able to kill human leukemic cells and colon cancer cells by apoptosis.^[2][3]

References

1. Good Scents Company
2. Dimas, Kostas; Kokkinopoulos, Dimitrios; Demetzos, Costas; Vaos, Basilios; Marselos, Marios; Malamas, Mixalis; Tzavaras, Theodoros (1999). "The effect of sclareol on growth and cell cycle progression of human leukemic cell lines". Leukemia Research 23 (3): 217–234. doi:10.1016/S0145-2126(98)00134-9. PMID 10071073.
3. K. Dimas; Hatziantoniou, S; Tseleni, S; Khan, H; Georgopoulos, A; Alevizopoulos, K; Wyche, JH; Pantazis, P; Demetzos, C (2007). "Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice". Apoptosis 12 (4): 685–694. doi:10.1007/s10495-006-0026-8. PMID 17260186.