Cedrol

ChemicalBook > CAS DataBase List > 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

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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)
form: Solid
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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 22135
Product name: (+)-Cedrol
Purity: ≥99.0% (sum of enantiomers, GC)
Packaging: 5g
Price: $109
Updated: 2024/03/01

Sigma-Aldrich

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

TCI Chemical

Product number: C2854
Product name: Cedrol
Purity: >98.0%(GC)
Packaging: 5g
Price: $112
Updated: 2024/03/01

TCI Chemical

Product number: C2854
Product name: Cedrol
Purity: >98.0%(GC)
Packaging: 25g
Price: $247
Updated: 2024/03/01

Cayman Chemical

Product number: 25769
Product name: (+)-Cedrol
Purity: ≥98%
Packaging: 100mg
Price: $68
Updated: 2024/03/01

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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

Cedarwood oil

Preparation Products

Cedryl acetate Methyl cedryl ether

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Cedrol Suppliers

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View Lastest Price from Cedrol manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: Cedrol 77-53-2
Price: US $120.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-05-24

Hebei Weibang Biotechnology Co., Ltd

Product: Cedrol 77-53-2
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-01

Hebei Kingfiner Technology Development Co.Ltd

Product: Cedrol 77-53-2
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-06-24

77-53-2, CedrolRelated Search:

Sodium bis(trimethylsilyl)amide N-Methyl-2-pyrrolidone POLY(METHYLSILSESQUIOXANE) N,N-Dimethyldodecylamine Hexamethyldisilazane METHYL-2-PYRROLIDONE Cyclooctane CYCLOOCTANEMETHANOL CEDROL ACETATE,Acetic acid, cedrol ester CEDROL ACETATE 8,9-Epoxy cedrane cedrol,cedar camphor,cypress camphor,CEDROL(SG) CEDRENOL,cedrenol,cedr-8(15)-en-9-ol cedrol methyl ether n-Hendecane CEDRENE BICYCLO(3.3.0)OCTANE CEDROL FLUESSIG

(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

CYPRESS CAMPHOR

(+)-CEDROL

CEDROL

CEDAR CAMPHOR

CEDRENOL B

(+)-Cedrol, 98%, from Cedrus deodara (Roxb. ex Lamb.) G. Don

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

2,6,6,8-tetramethyltricyclo[5.3.1.0~1,5~]undecan-8-ol

CEDROL CRYSTALS

CEDROL LIQUID

CEDROL WITH GC

(+)-Cedrol, (1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol

OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3A-7-METHANOAZULEN-6-OL

OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3ALPHA,7-METHANOAZULEN-6-OL

(3R,6R)-2,3,4,5,6,7,8,8a-Octahydro-3,6,8,8-tetramethyl-1H-3aα,7α-methanoazulen-6-ol

Cedrol,(+)-Cedrol, (1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol

(+)-Cedrol >=99.0% (suM of enantioMers, GC)

(+)-Cedrol solution

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

8betaH-Cedran-8-ol

alpha-Cedrol

Cedran-8-ol

Cedrol crystal

[3R-(3alpha,3abeta,6alpha,7beta,8aalpha)]-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol

Cedrol,redistelled

CASMIERONE BY-PRODUCT

1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-

CEDROL CRIST.

CEDROL REDISTILLED

Cedrol &gt

(+)-Cedrol,0.98

Cypress brain

Kashiwagi brain

TIANFUCHEM--77-53-2--Cedrol

(3R,3aS,6R,7R,8aS)-3,6,8,8-Tetramethyloctahydro-1H-3a,7-methanoazulen-6-ol

77-53-2

2823-03-0

Complex Molecules

Chiral Building Blocks

Asymmetric Synthesis

Industrial/Fine Chemicals