Sclareol

Last updated
Sclareol
Sclareol.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 X mark.svgN
    Key: XVULBTBTFGYVRC-HHUCQEJWSA-N X mark.svgN
  • 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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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]

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. [2] 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. [3] [4]

Related Research Articles

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Free fatty acid receptor 3 protein is a G protein coupled receptor that in humans is encoded by the FFAR3 gene. GPRs reside on cell surfaces, bind specific signaling molecules, and thereby are activated to trigger certain functional responses in their parent cells. FFAR3 is a member of the free fatty acid receptor group of GPRs that includes FFAR1, FFAR2, and FFAR4. All of these FFARs are activated by fatty acids. FFAR3 and FFAR2 are activated by certain short-chain fatty acids (SC-FAs), i.e., fatty acids consisting of 2 to 6 carbon atoms whereas FFFAR1 and FFAR4 are activated by certain fatty acids that are 6 to more than 21 carbon atoms long. Hydroxycarboxylic acid receptor 2 is also activated by a SC-FA that activate FFAR3, i.e., butyric acid.

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<span class="mw-page-title-main">SUCNR1</span> Protein-coding gene in the species Homo sapiens

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Sodium-coupled monocarboxylate transporter 1 (i.e., SMCT1) and sodium-coupled monocarboxylate transporter 2 (i.e., SMCT2) are plasma membrane transport proteins in the solute carrier family. They transport sodium cations in association with the anionic forms (see conjugated base) of certain short-chain fatty acids (i.e., SC-FAs) through the plasma membrane from the outside to the inside of cells. For example, propionic acid (i.e., CH
3
CH
2
CO
2
H
) in its anionic "propionate" form (i.e., CH
3
CH
2
CO
2
) along with sodium cations (i.e., Na+) are co-transported from the extracellular fluid into a SMCT1-epxressing cell's cytoplasm. Monocarboxylate transporters (MCTs) are also transport proteins in the solute carrier family. They co-transport the anionic forms of various compounds into cells in association with proton cations (i.e. H+). Four of the 14 MCTs, i.e. SLC16A1 (i.e., MCT1), SLC16A7 (i.e., MCT22), SLC16A8 (i.e., MCT3), and SLC16A3 (i.e., MCT4), transport some of the same SC-FAs anions that the SMCTs transport into cells. SC-FAs do diffuse into cells independently of transport proteins but at the levels normally occurring in tissues far greater amounts of the SC-FAs are brought into cells that express a SC-FA transporter.

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References

  1. "Good Scents Company". Archived from the original on 2010-05-22. Retrieved 2010-03-18.
  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.