Sclareol
Names
IUPAC name
Labd-14-ene-8,13-diol
Systematic IUPAC name
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.450
KEGG
UNII
  • 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 ☒N
    Key: XVULBTBTFGYVRC-HHUCQEJWSA-N ☒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
  • CC1(C)CCC[C@@]2(C)[C@@]1([H])CC[C@@](C)(O)[C@@H]2CC[C@](O)(C)C=C
Properties
C20H36O2
Molar mass 308.506 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 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 also able to kill human leukemic cells and colon cancer cells by apoptosis.[2][3]

It has been considered that sclareol contained in clary sage oil has estrogen-like effects and is effective for amenorrhea, menstrual irregularities, and hot flashes during menopause.

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.[4] 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.

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. S2CID 42171668.
  4. ↑ Matsumoto, Y.; Horikawa, K. Transdermal Absorption of Sclareol, an Active Ingredient in Clary Sage Oil: A Complementary and Alternative Medicine for Menopausal Symptoms. Women 2022, 2, 304-312. https://doi.org/10.3390/women2030028
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