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Sclareol

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Sclareol
Names
IUPAC name Labd-14-ene-8,13-diol
Systematic IUPAC name (1R,2R,4aS,8aS)-1--2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.450 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: XVULBTBTFGYVRC-HHUCQEJWBX
SMILES
  • CC1(C)CCC2(C)1()CC(C)(O)2CC(O)(C)C=C
Properties
Chemical formula C20H36O2
Molar mass 308.506 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

Sclareol is a fragrant chemical compound found in 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.

In an experiment in which sclareol was dissolved in jojoba oil and applied to mice, sclareol was detected in the blood (transdermal absorption) 30 minutes after application. In this study, higher concentrations of sclareol were detected in liver homogenates than in blood. Although sclareol accumulation in the liver was suggested, it was concluded that no acute liver dysfunction was seen because AST and ALT were not elevated. Sclareol is also able to kill human leukemic cells and colon cancer cells in vitro by apoptosis.

References

  1. Good Scents Company
  2. Matsumoto, Yutaka; Horikawa, Kazumasa (2022). "Transdermal Absorption of Sclareol, an Active Ingredient in Clary Sage Oil: A Complementary and Alternative Medicine for Menopausal Symptoms". Women. 2 (3): 304–312. doi:10.3390/women2030028.
  3. 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.
  4. 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. S2CID 42171668.
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