77-53-2 Usage
Description
Cedrol is a sesquiterpene alcohol predominantly found in conifers of the genera Cupressus, Juniperus, and Cedrus. It exhibits significant anticancer properties, particularly against glioblastoma, through mechanisms such as cell growth inhibition, ROS generation, and DNA damage. Cedrol also shows synergistic effects with temozolomide in reducing drug resistance in glioblastoma treatment and has been observed to inhibit the growth of human renal adenocarcinoma, amelanotic melanoma cells, and induce autophagy and apoptosis in A549 non-small cell lung carcinoma cells.
Uses
Used in Pharmaceutical Industry:
Cedrol is used as an anticancer agent for its significant activity against glioblastoma, both in vitro and in vivo, through cell growth inhibition, ROS generation, and DNA damage.
Used in Pest Control:
Cedrol is used as an acaricide, serving as a natural alternative for pest control.
Used in Cosmetics Industry:
Cedrol is used as an enhancer for skin extracellular matrix (ECM) production, promoting skin health and regeneration.
Used in Chemical Synthesis:
(+)-Cedrol can be used as a starting material for the preparation of cedryl acetate through acetylation using acetic anhydride in the presence of an acid catalyst. Additionally, it can be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.
Preparation
From cedarwood by fractional distillation followed by recrystallization from suitable solvents of appropriate solid fractions.
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
Check Digit Verification of cas no
The CAS Registry Mumber 77-53-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 77-53:
(4*7)+(3*7)+(2*5)+(1*3)=62
62 % 10 = 2
So 77-53-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12+,14-,15+/m0/s1
77-53-2Relevant articles and documents
Characterization of a sesquiterpene cyclase from the glandular trichomes of Leucosceptrum canum for sole production of cedrol in Escherichia coli and Nicotiana benthamiana
Luo, Fei,Ling, Yi,Li, De-Sen,Tang, Ting,Liu, Yan-Chun,Liu, Yan,Li, Sheng-Hong
, p. 121 - 128 (2019)
Cedrol is an extremely versatile sesquiterpene alcohol that was approved by the Food and Drug Administration of the United States as a flavoring agent or adjuvant and has been commonly used as a flavoring ingredient in cosmetics, foods and medicine. Furthermore, cedrol possesses a wide range of pharmacological properties including sedative, anti-inflammatory and cytotoxic activities. Commercial production of cedrol relies on fractional distillation of cedar wood oils, followed by recrystallization, and little has been reported about its biosynthesis and aspects of synthetic biology. Here, we report the cloning and functional characterization of a cedrol synthase gene (Lc-CedS) from the transcriptome of the glandular trichomes of a woody Lamiaceae plant Leucosceptrum canum. The recombinant Lc-CedS protein catalyzed the in vitro conversion of farnesyl diphosphate into the single product cedrol, suggesting that Lc-CedS is a high-fidelity terpene synthase. Co-expression of Lc-CedS, a farnesyl diphosphate synthase gene and seven genes of the mevalonate (MVA) pathway responsible for converting acetyl-CoA into farnesyl diphosphate in Escherichia coli afforded 363 μg/L cedrol as the sole product under shaking flask conditions. Transient expression of Lc-CedS in Nicotiana benthamiana also resulted in a single product cedrol with a production level of 3.6 μg/g fresh weight. The sole production of cedrol by introducing of Lc-CedS in engineered E. coli and N. benthamiana suggests now alternative production systems using synthetic biology approaches that would better address sufficient supply of cedrol.
Process for the preparation of 8,14-cedranoxide
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, (2008/06/13)
Processes for the preparation of 8,14-cedranoxide are disclosed, according to which 8,14-cedrane diol is prepared by reducing 8,14-cedranolide by treatment with the aid of diisobutyl-aluminum hydride followed by acid hydrolysis, or 8,14-cedrane diol is cyclized with dimethyl sulfoxide.