Cedrol
- Product Name
- Cedrol
- CAS No.
- 77-53-2
- Chemical Name
- Cedrol
- Synonyms
- CEDROL CRYSTALS;alpha-Cedrol;CEDRENOL B;(+)-CEDROL;Cedrol crystal;(1S,2R,5S,7R,8R)-2,6,6,8-TETRAMETHYLTRICYCLO[5.3.1.01.5]UNDECAN-8-OL;1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-;CEDROL;Cedrol >Cedran-8-ol
- CBNumber
- CB1165544
- Molecular Formula
- C15H26O
- Formula Weight
- 222.37
- MOL File
- 77-53-2.mol
Cedrol Property
- Melting point:
- 55-59 °C(lit.)
- Boiling point:
- 273 °C(lit.)
- alpha
- D28 +9.9° (c = 5 in chloroform)
- Density
- 0.9479
- FEMA
- 4503 | (+)-CEDROL
- refractive index
- n20/D1.509-1.515
- Flash point:
- 200 °F
- storage temp.
- 2-8°C
- solubility
- Soluble in DMSO (10 mg/ml)
- 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
- 14,1911
- 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
- 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)- (77-53-2)
Safety
- Safety Statements
- 22-24/25
- 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 and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 22135
- Product name
- (+)-Cedrol
- Purity
- ≥99.0% (sum of enantiomers, GC)
- Packaging
- 5g
- Price
- $109
- Updated
- 2024/03/01
- Product number
- CRM40903
- Product name
- (+)-Cedrol solution
- Purity
- certified reference material, 2000?μg/mL in methanol, ampule of 1?mL
- Packaging
- 1mL
- Price
- $109
- Updated
- 2022/05/15
- Product number
- C2854
- Product name
- Cedrol
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $112
- Updated
- 2024/03/01
- Product number
- C2854
- Product name
- Cedrol
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $247
- Updated
- 2024/03/01
- Product number
- 25769
- Product name
- (+)-Cedrol
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $68
- Updated
- 2024/03/01
Cedrol Chemical Properties,Usage,Production
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
acaricide, enhances skin ECM production
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
In fragrances.
Definition
A tertiary terpene alcohol.
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
Cedrol Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Cedrol manufacturers
- Product
- Cedrol 77-53-2
- Price
- US $20.00/kg
- Min. Order
- 1kg
- Purity
- 99.9%
- Supply Ability
- 200000kg
- Release date
- 2024-04-26
- Product
- Cedrol 77-53-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2023-12-25
- Product
- Cedrol 77-53-2
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 100000tons
- Release date
- 2023-08-14