| Identification | More | [Name]
Cedrol | [CAS]
77-53-2 | [Synonyms]
(1S,2R,5S,7R,8R)-2,6,6,8-TETRAMETHYLTRICYCLO[5.3.1.01.5]UNDECAN-8-OL
(1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.0]undecan-8-ol
8-Cedren-13-ol
CEDAR CAMPHOR
CEDRENOL
CEDRENOL B
(+)-CEDROL
CEDROL
CYPRESS CAMPHOR
OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3A-7-METHANOAZULEN-6-OL
OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3ALPHA,7-METHANOAZULEN-6-OL
Octahydro-3,8,8-trimethyl-6-methylene-1H-3a,7-methanoazulen-5-ol
1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, [3R-(3alpha,3abeta,6alpha,7beta,8aalpha)]-
1h-3a,7-methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-,(3r-(3-alpha,3a-bet
1h-3a,7-methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-,[3theta-(3alpha,3
6alpha,7beta,8aalpha)]-abet
7-beta,8a-alpha))-6-alpha
7-methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-,(3r-(3-alpha,3a-beta,6-alpha,7-beta,8a-alpha))-1h-3
7-Methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-,[3R-(3.alpha.,3a.beta.,6.alpha.,7.beta.,8a.alp1H-3a
8-betah-cedran-8-ol | [EINECS(EC#)]
201-035-6 | [Molecular Formula]
C15H26O | [MDL Number]
MFCD00062952 | [Molecular Weight]
222.37 | [MOL File]
77-53-2.mol |
| Chemical Properties | Back Directory | [Definition]
A tertiary terpene alcohol. | [Appearance]
Colorless crystals; cedarwood odor. soluble in 11 parts of 95% alcohol. Combustible. | [Melting point ]
55-59 °C(lit.) | [alpha ]
D28 +9.9° (c = 5 in chloroform) | [Boiling point ]
273 °C(lit.) | [density ]
0.9479 | [FEMA ]
4503 | (+)-CEDROL | [refractive index ]
n20/D1.509-1.515 | [Fp ]
200 °F
| [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (10 mg/ml) | [form ]
neat | [pka]
15.35±0.60(Predicted) | [color ]
White | [Odor]
at 100.00 %. cedarwood woody dry sweet soft | [Odor Type]
woody | [optical activity]
[α]20/D +10.5±1°, c = 5% in chloroform | [JECFA Number]
2030 | [Merck ]
13,1923 | [BRN ]
2206347 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [LogP]
4.33 | [CAS DataBase Reference]
77-53-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Cedrol(77-53-2) | [EPA Substance Registry System]
77-53-2(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
2
| [RTECS ]
PB7728666
| [HS Code ]
29062990 | [Hazardous Substances Data]
77-53-2(Hazardous Substances Data) | [Toxicity]
LD50 skin in rabbit: > 5gm/kg |
| Hazard Information | Back Directory | [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). | [Uses]
(+)-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. | [Uses]
acaricide, enhances skin ECM production | [Uses]
In fragrances. | [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. | [storage]
4°C, protect from light | [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 |
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