Cedrol

Description

Cedrol is a sesquiterpene alcohol found in conifers mainly of the genera Cupressus, Juniperus, and Cedrus. It has been found to possess significant anticancer activity against glioblastoma in vitro and in vivo via cell growth inhibition, ROS generation, and DNA damage.1 Cedrol also displayed synergistic effects with temozolomide against glioblastoma in vitro and in vivo via reduced expression of drug resistance proteins.1,2 Cedrol inhibited the growth of human renal adenocarcinoma and amelanotic melanoma cells3 and induced autophagy and apoptosis in A549 non-small cell lung carcinoma cells4.

Chemical properties

Colorless crystals; cedarwood odor. soluble in 11 parts of 95% alcohol. Combustible.

Occurrence

Found in the wood of several conifers, particularly cypresses and cedars, including Cedrus atlantica, Cupressus sempervirens, Juniperus virginiana (Fenarolfs Handbook of Flavor Ingredients, 1971).

The Uses of Cedrol

acaricide, enhances skin ECM production

The Uses of Cedrol

In fragrances.

The Uses of Cedrol

(+)-Cedrol can be used as a starting material for the preparation of cedryl acetate by acetylation using acetic anhydride in the presence of an acid catalyst. It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.

Definition

A tertiary terpene alcohol.

What are the applications of Application

(+)-Cedrol is a major component of cedarwood oil

Preparation

From cedarwood by fractional distillation followed by recrystallization from suitable solvents of appropriate solid fractions.

General Description

(+)-Cedrol is a crystalline hydrated product of α-cedrene, which is a sesquiterpene found in cedar-wood oil. It can be used as a fragrance ingredient in cosmetics, shampoos, and soaps as well as in non-cosmetic products such as cleaners and detergents. (±) Cedrol can be synthesized by intramolecular Diels-Alder reaction of alkyl cyclopentadiene.

Purification Methods

Purify cedrol by recrystallisation from aqueous MeOH. It is estimated colorimetrically with H3PO4 in EtOH followed by vanillin and HCl [Hayward & Seymour Anal Chem 20 572 1948]. The 3,5-dinitrobenzoyl derivative has m 92-93o. [Stork & Clarke J Am Chem Soc 83 3114 1961, Beilstein 6 III 424.]

References

Chang et al. (2020), Cedrol suppresses glioblastoma progression by triggering DNA damage and blocking nuclear translocation of the androgen receptor; Cancer Lett., 495 180 Chang et al. (2020), Cedrol, a Sesquiterpene Alcohol, Enhances the Anticancer Efficacy of Temozolomide in Attenuating Drug Resistance via Regulation of the DNA Damage Response and MGMT Expression; J. Prod., 83 3021 Loizzo et al. (2008), Antiproliferative effects of essential oils and their major constituents in human renal adenocarcinoma and amelanotic melanoma cells; Cell Prolif., 41 1002 Zhang et al. (2016), Cedrol induces autophagy and apoptotic cell death in A549 non-small cell lung carcinoma cells through the PI3K/Akt signaling pathway, the loss of mitochondrial transmembrane potential and the generation of ROS; Int. J. Mol. Med., 38 291